In My Footsteps: A Gen-X Nostalgia Podcast

Episode 254: The Sad Genius of Robin Williams, Chappelle's Show, Collectible Investment Fails(7-29-2026)

Christopher Setterlund Season 1 Episode 254

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0:00 | 1:03:33

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The sad genius of Robin Williams. The undeniable impact of Chappelle's Show. Some of the biggest collectibles trends that were investment fails.

Episode 254 is loaded with legends and icons.

Robin Williams was one of the most talented actors and comedians of his or any generation. He could be a ball of manic energy in comedy, a relatable everyman, and even a terrifying killer. Though he entertained millions in movies and television, there was an underlying sadness to him. We look back at the life and legacy of a one-of-a-kind.

In the annals of television history, few shows have lasted such a short time but made such a huge impact. Chappelle's Show changed the way sketch comedy was written and received by the audience. Groundbreaking characters, memorable sketches, dozens of quotable lines. This show achieved more in 28 episodes than many do in several hundred.  

A new Top 5 will have you searching the attic and basement. Some investments pay off; these are not those. We will look at some collectibles that we thought would grow in value, but sadly they ended up flopping and collecting dust in a corner. How many of these collectibles investment fails did you own?

Of course, there is a brand-new This Week In History and Time Capsule, looking at the first cross-country trip by automobile.

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Listen to Episode 253 here

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0:02

Hello world, and welcome to the In My Footsteps podcast.

I am Christopher Setterland, coming to you from the vacation destination known as Cape Cod, MA.

And this is episode 254.

We're ending the month of July with one of the most loaded shows ever, at least in my opinion, and I can't wait to get started.

0:26

We're going to kick it off with a look back at the life and career of one of the funniest, most talented comedians and actors ever, Robin Williams.

We're going to go way back to the beginning of the 21st century at one of the funniest and most influential TV shows of this century, Chappelle's Show.

0:46

We're going to laugh, cry, and shake our heads at a new top five as we look at the top five collectibles that ended up being investment fails.

Did you blow your money on any of these?

And there's going to be a brand new This Week in History and Time capsule looking back at the conclusion of the very first cross country automobile trip.

1:07

All of that is coming up right now on episode 254 of the In My Footsteps podcast.

So what are we going to talk about this week?

How I have set the bar so high by saying this is one of the most loaded shows I can remember.

1:23

Does that make you more excited to listen to the show or does it make you think that the other shows I've done have not been loaded?

I think they're all good.

Listen to all of them.

But this one, though, you heard the intro there, it became more coincidence timing as far as when this show is going up, as far as what was being promoted.

1:42

I try to do a lot of these things happened this Week in History besides the actual This Week in History segment.

So that's where Robin Williams and Chappelle Show come in.

But we'll get into that.

Thank you all so much for tuning in, whether this is your first show, your 254th show.

2:00

Actually, I think there's more, including the hidden tracks and mixtapes.

This is your weekly dose of Gen.

X nostalgia, whether you're Gen.

X or Millennial or Boomer or, I mean, maybe Gen.

Z.

You don't have to be from Cape Cod like me, or New England or even the United States.

2:18

It's all good, it's all fun, and I'm so glad all of you are here to check it out.

Now that I've set the bar high.

And before we get into the meat of the podcast sandwich, you know I can't start off any show without thanking my Patreon subscribers.

So big thanks to Laurie, Mary Lou, Ashley, Kevin, Leo, Marguerite, Neglectoid, Crystal, Matt, Doctor, Shrimp, Porto Chico.

2:45

Thank you all so much for being my biggest backers, my biggest supporters, those who literally put their money where their mouth is to support me.

My never ending quest to be a full time self-employed content creator.

You too can get a shout out on the podcast and be held in such high regard by me by becoming a Patreon member.

3:06

I've got several tiers starting as low as $3 a month.

I've got a free tier.

You, if you're a paying member, get access to bonus podcasts like the members Only podcast, early access to the hidden track podcasts, you get access to the remastered without a map, live streams, early access to YouTube videos, and so much else.

3:29

And one more thing before we dive in, check out at the top of the podcast notes the link to the GoFundMe, the fundraiser for my feature film The Cabin.

There's still a few weeks left in the fundraiser, so if you want to donate any amount helps bring my feature film debut to life, a story that I wrote almost 20 years ago.

3:50

It's amazing that it's going to be a feature film next year with streaming and Blu-ray copies and hopefully a limited theatrical release around where I live.

I wanted to make sure I mentioned it at the top of the podcast because to pull back the curtain this past week I did an awesome author event at the Dennis Public Library and I brought a sheet that I created a flyer for the feature film for the fundraiser.

4:17

And then at the end of the event, I forgot to talk about it at all.

So I'm looking at this sheet like, why did I even bring it?

It's basically was there to blow around in the AC.

So please check it out, donate if you can, share if you can.

4:32

And obviously there's going to be a lot more info to come because we're about a month out from me going on the road to shoot this film.

But that's in the future.

Let's go back to the past.

Get ready to get your funny bones tickled as we look back at the life and career of one of the funniest men ever on this planet, Robin Williams.

4:55

There's going to be very little that I can share about Robin Williams that isn't pretty common knowledge.

He is, in my opinion, and I'm sure a lot of yours, one of the funniest, most talented comedians and actors, maybe of all time.

5:14

At the very least, there are few other entertainers in modern history that have possessed the range, creativity, and emotional depth of Robin Williams.

His career spanned nearly 4 decades and it felt like he was going to be a part of the zeitgeist of American entertainment forever.

5:35

It was amazing and inspiring to see him go from kind of a wacky, goofy comedian into one of these actors that crossed over.

He did way more serious movies, he did some creepy ones.

And in the end, it was his rapid fire wit, his boundless imagination and energy, and that genuine humanity that made him one of the defining entertainers of my lifetime, and I'm sure a lot of yours.

6:02

Robin Williams was born July 21st, 1951 in Chicago, IL.

His father, Robert, was a senior executive at the Ford Motor Company, with his mother Laurie being a successful model before raising a family.

Despite living in a financially comfortable household, Robin was often lonely because his father worked long hours and frequently traveled.

6:26

His mother maintained a busy social life, so Robin spent much of his childhood entertaining himself.

Many biographers believe that this isolation in his childhood helped to develop the imagination that later fueled his comedy.

Contrary to what you would see on camera and in public, Robin was painfully shy as a child, struggling socially.

6:50

He discovered, though, that if he could make people laugh, they liked him, and comedy became both his shield and his language.

In 1967, the Williams family moved to Marin County, California, where Robin attended Redwood High School.

7:07

He then briefly attended Claremont Men's College, transferring quickly to the College of Marin, where he focused on theater.

He then earned admission to the Juilliard School in New York City where only a handful of students were accepted into the advanced acting program.

7:25

One of his classmates became one of his closest lifelong friends, and that was Christopher Reeve, the future Superman.

Reeve later said that Robin Williams possessed more raw talent than anyone he had ever met.

It was while at Juilliard and shortly after graduating that Robin discovered his love of stand up comedy.

7:46

He was different than most other comics of the era, rarely relying on traditional joke structures, instead exploding onto the stage with lightning fast character changes, celebrity impressions, original voices, absurd observations, completely improvised conversations.

8:06

If you weren't ready for Robin Williams, you could quickly get overwhelmed, like being in a tidal wave.

It didn't take long for the entertainment world to recognize Robin.

In 1978, television producers needed an unusual alien character for an episode of Happy Days.

8:25

Robin auditioned, improvised nearly everything, astonishing the producers, and he became Mork from Orc.

As a kid growing up in the 1980s, Mork and Mindy was the 1st that I remember Robin Williams.

8:41

The show was on for Four Seasons and 95 episodes from 1978 to 1992.

It immediately made Robin Williams one of America's biggest TV stars overnight and earned him Golden Globe and Emmy nominations.

8:57

In addition to Mork and Mindy, My introduction to Robin Williams is maybe one of his lesser known films or probably forgotten based on his whole catalog.

And that was 1980s Popeye.

I loved the Popeye cartoons, so a live action version of it was bound to be fun for me.

9:17

I mean, I was a little kid.

Only Robin Williams could have perfectly captured Popeye's strange voice and his physical mannerisms.

The movie was a modest hit, 60% fresh on Rotten Tomatoes, making $60 million on a budget of 20 million.

9:35

Just those two things there, Popeye and Mork and Mindy, would have left a nice mark on me as an 80s child.

But even from the beginning, Robin Williams was dipping his toes into things besides his manic comedy.

In the 80s, he had The World According to Garp, Moscow on the Hudson, Good Morning Vietnam, Dead Poet Society.

9:58

It's funny, as I pause here, I realized when doing a segment about the life of Robin Williams, just how overwhelmingly huge and important his contributions were that I would be kind of speed running a lot of his career.

That's why just as I was naming those movies, I'm like, Oh my God.

10:15

I could probably stop and talk about each one for several minutes, but this podcast has several segments.

I think 1 of Robin's unique traits, and one of the things that made him sort of an anomaly in the world of acting was the fact that he became a master of both comedy and drama, sometimes weaving in and out of those effortlessly in the same movie.

10:39

Just look at what he did in the early 90s.

He went from Awakenings alongside Robert De Niro to The Fisher King, which is considered one of his greatest dramatic performances.

But then he went into the goofiness of Hook, where he appropriately played the adult version of Peter Pan.

10:57

He had one of his greatest performances ever without ever being seen on the movie screen when he was the Genie in Aladdin in 1992.

That is considered one of the greatest vocal performances ever recorded, with Robin recording hundreds of improvised jokes, celebrity impressions, alternate takes.

11:17

He really changed the possibilities of animated voice acting.

Your opinion may vary, but I think his most famous live action role was Missus Doubtfire in 1993, where he disguises himself as an elderly housekeeper to be able to be among his children as he's going through a divorce.

11:40

The 90s also saw him starring as a child in a man's body in Jumanji in 1995.

I remember seeing that at the theater and being fascinated by the pretty good for the time CGI.

Yes, it's not as good as how it is today, but you got to remember I grew up in a time when CGI was barely being used in the 1980s, so seeing all the animals come to life in Jumanji was huge.

12:06

He starred in The Birdcage in 1996 opposite Nathan Lane.

You can see it's hit after hit and they're all different types of movies.

Yes, he would have moments of being kind of manic with the humor in most of his films, but Robin Williams was so deep and so versatile that you never fully knew what his character was going to do, but you knew you wanted to watch.

12:33

No look at the career of Robin Williams is complete without Goodwill Hunting, which is in my opinion, in a lot of people's opinion, the greatest acting achievement of Robin Williams career.

He just commands your attention every time the camera's on him.

12:50

Playing therapist Sean Maguire, this performance won him the Academy Award for Best Supporting Actor and he gave in my opinion one of the best acceptance speeches where it was the perfect summary of who Robin Williams was.

The mixture of gratitude and humor just effortlessly rolled together.

13:10

At this point in the late 90s, early 2000s, Robin Williams is getting towards 50 years old.

He's like my age now.

He could have easily coasted on roles similar to what he had done, but instead he shocked a lot of people by diving into some darker roles, some horror roles, including back-to-back movies in 2002, One Hour Photo, and Insomnia.

13:36

In One Hour Photo, he has the bleach blonde hair and he's a lonely photo tech who becomes obsessed with a family.

In Insomnia, he was a calculating murderer playing opposite Al Pacino.

You might have started those movies off thinking of the genie in Aladdin or Popeye, but by the end you were terrified of Robin Williams because he was so good at basically everything he did.

14:03

Some of the younger listeners might know Robin Williams mostly for his role as Theodore Roosevelt in the Night at the Museum franchise.

That or Aladdin.

Over the course of his career he did comedy, he did more serious roles in movies, he was on TV, he kept doing stand up comedy.

14:24

In his career he won an Academy Award, 6 Golden Globes, 2 Emmys, 5 Grammys, 2 Screen Actors Guild Awards, the Cecil B DeMille Award for Lifetime achievement.

But this is where you start to see that the public face and the private life sometimes don't match up.

14:46

Robin freely discussed his struggles with cocaine and alcohol addictions during the late 70s and early 80s, with the 1982 death of his friend John Belushi becoming a major turning point.

This is where he gave up on cocaine, but years later he relapsed with alcohol.

15:05

He kept seeking treatment and remained candid about his recovery, inspiring people in a totally different way.

Later in his life, in the early 20 TENS, Robin Williams began experiencing symptoms like anxiety, insomnia, memory problems, tremors, difficulty concentrating.

15:25

Initially, doctors believed he had Parkinson's disease.

It was found after his death that he was actually suffering from something called Lewy body dementia, which was a progressive neurological disease that can cause severe cognitive impairment, hallucinations, mood changes, sleep disturbances and movement problems.

15:46

Medical experts have since described Robin's case as one of the most severe instances of the disease they had ever encountered.

On August 11th, 2014, Robin Williams died at his home in Tiburon, CA at the age of 63.

16:04

His death was ruled a suicide.

Subsequent medical findings made clear that the previously undiagnosed Lewy body dementia had profoundly affected his brain and behavior in the months leading up to his death.

His death is one of the few in entertainment where I can specifically remember where I was and what I was doing when I heard of it.

16:28

Still to this day.

I was out for a long run.

I was running down by the beach.

I was kind of winded from running, so I paused my running app.

I opened up my phone just to take a moment for a distraction.

And there on Twitter, when it was still Twitter, was the news of Robin Williams death.

16:47

It had already been ruled a suicide.

And it didn't match up in my head that one of the friendliest, warmest, funniest people I'd ever seen in entertainment could be so sad behind the scenes that he would decide to take his own life.

17:05

This was before we knew about the Lewy body dementia.

It was hard to wrap my head around that one of the funniest men ever was just so depressed behind the scenes.

Outside of the death of Nirvana frontman Kurt Cobain, I think the death of Robin Williams affected me the most as far as entertainment went.

17:25

I literally stopped, took a picture of the scenery where I was to never forget, and posted it everywhere.

It really affected me.

I'm sure it really affected a lot of you, but I have dealt with severe bouts of depression in my life and I know how strange and lonely and confusing depression can be.

17:47

And that was what I was assuming when he had committed suicide, that it was depression, not the Lewy body dementia.

I chose this particular moment to put this segment in the podcast because it's kind of a halfway between his birthday and his death day.

18:04

I wanted to make sure that we celebrated his life a lot in this segment, but I also didn't want to gloss over how impactful his death was.

There are no limits to the amount of amazing movies and TV shows and content that Robin Williams left behind.

18:21

You've got manic comedy like Mork and Mindy.

You've got tremendous movies like Good Morning Vietnam, Dead Poets Society, Misses Doubtfire, The Bird Cage, Goodwill, Hunting, the Night at the Museum franchise.

You can go on YouTube and just type in Robin Williams clips and you're going to find something that makes you happy.

18:42

Appearances on talk shows, His friendship with Coco the gorilla, even his lowest rated films like Old Dogs in 2009 which is 5% fresh on Rotten Tomatoes.

It has Nuggets of great Robin Williams in there.

18:58

He inspired generations of performers, comedians, character driven actors, but more importantly, Robin Williams demonstrated that humor and vulnerability could coexist.

His performances consistently balanced that between exuberant comedy with empathy, emotional honesty.

19:19

You felt that no matter what he was doing, the human Robin Williams was there and he was approachable.

He was someone.

If you saw him on the street, you thought he'd be friendly.

More than a decade after his passing, his performances remain timeless.

19:34

They remind us of the rare gift he possessed, the ability to make people laugh, cry and feel understood, sometimes all within the same scene.

This week in history we are going back 123 years to July 26th, 19 O3 and the very first cross country automobile trip ending in New York City.

20:06

Today, driving coast to coast is not a big deal.

I mean it takes a long time, usually around a week.

In 2001, I took a bus from Las Vegas to Cape Cod.

It took about 4 1/2 days today.

20:21

When driving cross country or long distances, you take for granted things that we have GPS navigation, gas stations every few miles, roadside hotels available around the clock, even paved roads.

Back in 19 O3, there were none of these conveniences.

20:41

There was no Interstate highway system, and most Americans hadn't even seen an automobile, much less believe that one could travel thousands of miles.

It seemed like that was an impossible undertaking and during the summer of 19 O3 Doctor Horatio Nelson Jackson undertook the seemingly impossible challenge and succeeded.

21:03

At the time when Jackson started his trip, there were only about 33,000 registered automobiles in the United States.

Today that number is somewhere around 298,000,000 and I'm sure probably a few that aren't registered.

21:21

The adventure began on May 18th, 19 O3 with Doctor Horatio Jackson, who lived in Burlington, Vt, was out in California visiting the state with his wife, Bertha.

It was while relaxing at San Francisco's University Club that he overheard a discussion in which several men insisted that crossing America by automobile was impossible.

21:45

Jackson disagreed, and before long he accepted a $50 wager that an automobile could be driven across the continent in under 90 days.

If you're wondering, that bet would work out to just under $1900 today.

22:01

One of the funniest things about this whole thing is that at the time, Jackson didn't even own a car and he had almost no driving experience.

That would be like someone betting me that you couldn't take a submarine around the world and me saying, OK, for $1900 I'll do it.

22:17

And then I have to go get a sub and learn how to drive a sub.

I mean, I know I can eat a sub sandwich, but I don't know if I could drive one for this trip.

Jackson would eventually locate a used 19 O 3 Winton touring car owned by a Wells Fargo executive.

22:35

The car already had 1000 miles on it, but Jackson paid approximately $3000 for the car that he would name the Vermont.

That $3000 is equal to just over $113,000 when adjusted for inflation.

22:51

What did he get for that $3000?

A two cylinder engine, 20 horsepower chain drive, two forward gears, one reverse gear, top speed of a whopping 30 miles an hour, no roof, no windshield and a wooden body.

23:10

Jackson hired 22 year old mechanic Sewell Crocker to come along with him 'cause he was an auto mechanic and there weren't service stations.

In fact, they had to pack sleeping bags, cooking equipment, rain gear, tools, spare parts.

23:26

They weren't just packing to travel, they were packing to live.

It's like they were going camping across the country.

The trip began May 23rd, 19 O3, with the car being ferried from San Francisco to Oakland.

Within 15 miles they suffered a flat tire.

23:44

At this time, the roads were barely roads.

There were no highways much of the western United States.

They had to follow wagon trails, railroad right of ways, river valleys, cattle paths.

Sometimes they just drove across open land hoping that it led to somewhere useful.

24:04

Just imagine you walking across the country and just stepping out your front door and just walking wherever you are across the street and just going that way.

That's kind of what they did.

There were constant issues with broken chains, bent axles, blown tires.

24:22

Luckily, he had a mechanic.

You would have mud and sand with them having to dig the car out by hand.

But this trip was one of the most fascinating events at the time.

Outside of major cities, most Americans had never even seen an automobile.

24:40

You had crowds gathering when they went by, kids chasing it, farmers stopping to watch.

In Idaho, 1/3 member was brought aboard the team with Jackson purchasing a bulldog named Bud.

On July 26th, 19 O 363 days, 12 hours and 30 minutes after leaving San Francisco, the battered Winton automobile rolled into New York City.

25:07

They had traveled approximately 5600 miles.

If you're wondering, I just put it in on Google Maps.

If you were to drive from San Francisco to New York City today, the quickest route is 2906 miles.

That's a little more than half of what they drove because there are highways today, even if you avoid highways, the quickest distance is still 3121 miles.

25:34

So that's a lot of open fields they drove through.

The Wynton automobile barely survived the trip back to Vermont, but the significance of that trip can't be overstated.

It helped to cement the automobile as something that could be practical transportation.

25:52

It inspired improved highway and Rd. constructions, made cross country vacations more common, made automobile tourism more common.

Today, that famous Winton, Vermont automobile, as Jackson called it, remains around today as it's preserved by the Smithsonian's National Museum of American History.

26:15

Jackson went on to enjoy a distinguished career as a physician, businessman, newspaper owner, banker, radio station owner and decorated Army medic during World War One.

But he's probably remembered most for his trip across the country via automobile.

26:34

And that first cross country automobile trip ended in New York City 123 years ago this week in history.

Now we open up a brand new time capsule.

For this one, we're going back 32 years to July 30th, 1994.

26:56

My sisters Lindsay and Ashley would have been turning 10 years old.

What was going on in the world of pop culture back then?

Well, let's find out.

The number one song was I swear by All for One.

This song was originally a country music hit for John Michael Montgomery in 1993.

27:17

The All for One version spent 11 weeks at #1.

This song was everywhere my sophomore year of high school.

This song made All For One's debut album, also called All For One, a major hit, and the song won a Grammy for Best Pop Performance by a Duo or Group With vocal.

27:38

It's a lot of words that just don't go together.

The album has gone on to sell around 5 million copies worldwide.

The number one movie was The Mask and you could get into the theater with a ticket costing $4.08.

27:55

We talked earlier about the manic comic energy of Robin Williams.

Jim Carrey is right up there with him.

This is the movie about that loser Stanley Ipkiss finding the mysterious mask that turns him into the green faced superhero.

28:13

The movie was a massive hit, making over $350 million on a budget of somewhere between 18 and 23 million.

It made Jim Carrey A bankable star.

It also introduced the world to Cameron Diaz and also led to one of the worst movies of all time with Son of the Mask.

28:33

Son of the Mask made $60 million, which sounds good until you hear that the budget was up close to 100 million.

Sorry to the few of you that find Son of the Mask better than the original.

The number one TV show was Home Improvement.

28:52

This starred Tim Allen Is Tim the Toolman Taylor, a quintessential 90s show because it was on from 1991 to 99.

In total, there were eight seasons, 204 episodes, with the show being in the top ten of ratings every single year, topping as high as #2 in the ratings for season 3 in 1993.

29:17

And if you were around back then, July 30th, 1994, perhaps you had some money to burn and you were looking to invest in a home computer.

Well, I've got a deal for you.

Or possibly a deal.

At Best Buy, you can get yourself an Acer Multimedia Home Computer system.

29:38

It has a 420 megabyte hard drive.

Free Harvard graphics come with this computer.

It's preloaded with the original Microsoft Windows Prodigy, not the Band, QuickBooks and Carta for some reason.

29:56

Some kind of golf CD, internal facts, and for some reason they promote a double spin CD-ROM drive.

All this costs you 1998 dollars, or about $4500 when adjusted for inflation to 2026.

30:17

If you really want this computer, you can probably go to the dump right now and find 1.

So yay, that'll wrap up a new time capsule and another this week in history.

If you think that Acer computer was an investment failure, boy, if I got some for you, we got a brand new top five as we will laugh, cry and shake our heads at the things that we wasted money on that we thought would be our retirement fund.

30:45

So let's look at some collectibles that were investment fails.

We've heard of get rich quick schemes, pyramid schemes, Ponzi schemes, anything that people can do to make as much money as possible in his little time with little effort.

31:07

I guess collectibles would be kind of a get rich slow scheme.

You put a lot of faith in.

The things that you're spending money on now are going to increase in value so that years from now you can look back and point fingers at people and say, see, told you I was smart.

31:24

Unfortunately, many of these collectibles end up not being worth anything, or at least so little that it doesn't justify the amount of time and money you put into them.

What we're going to do now is a brand new top five.

Looking at the top five collectibles that were investment fails, there was one in particular that started this whole thing off mine that I was the biggest culprit in wasting money on, but then it opened it up to a lot of different ones.

31:54

How many of these have you wasted money on or warned other people to not spend their money on?

As with most of the top fives, they are in no particular order.

There are also some honorable mentions.

I hope as I mentioned these you're not staring at one of these covered in cobwebs and crying, but let's get into it.

32:16

Honorable mentions for collectible investment fails include the Power of the Force 2 Star Wars figures.

These were from the mid 1990s, meant to capitalize on the original Star Wars figures.

32:32

The difference was they manufactured way, way too many.

You can get graded ones that are worth about 5 to $10 to this day.

Another honorable mention is the 1990s McDonald's Happy Meal toys.

32:49

This was the peak of McDonald's putting out things that you thought would be worth a lot.

They had sets of things, Super Mario 3, Power Rangers, Mcnugget Buddies.

In rare cases, unopened sets of some of these might fetch you a few $100.

33:07

But how much did you spend on fast food to get them?

Another honorable mention is Funko Pops.

These are still around today, still popular and still pretty easy to find.

Which is why they are not worth much.

33:23

It is because they have been mass produced.

When they were first seen to be popular, companies capitalized and made way way too many.

So you can find them everywhere, which makes them virtually worthless except in some extreme cases.

Another honorable mention is the 50 State Quarters program.

33:44

These were released between 1999 and 2008.

Unless you have a rare uncirculated coin and a complete set displayed, these quarters are worth exactly what their amount says. 50 quarters At $0.25, you've got yourself $12.50.

34:05

And the final honorable mention is the 1980s porcelain dolls.

These are another victim of being mass produced when the collectibles started to become a craze in the country.

Very specific dolls might get you a little more, but for the most part they are valued at anywhere between 10 and $30.

34:27

And when they were selling in the 80s for anywhere from 20 to $100.

You can see where this was a fail.

So those are the honorable mentions.

How many of those did you waste money on?

I think at one point I was trying to collect those 50 state quarters, but it just became too much of a pain, so I gave up.

34:45

And luckily.

And then when I go spending $50.00 to get that last quarter I needed and then, yeah, it's worth $0.25.

Oh, but I am not immune from collectibles fails.

And we're going to find out at the very beginning with the actual top five, starting with #1 Beanie Babies. 1st I got pinky then I got pinky.

35:08

I got pinky and Patty in the same week.

Would Vanessa catch something Teeny beanie baby I just now at McDonald's your kids can get teeny beanie babies and a happy meal.

Real Thai Beanie Babies and a mini size.

Oh, so cute and so many different little animals.

35:24

Oh, they're going to be worth a ton.

And here we are 25 years later.

They are virtually worthless.

These were all sorts of different animals, mostly bears.

Those were the ones I remember with the tie tag on the ear.

35:40

Different cute names.

These were created by Tie Warner and originally introduced in 1993.

They were seen as the very first Internet sensation.

I obviously fell for it.

At my mother's house.

35:55

I have a giant grey tote that is filled with Beanie Babies, A lot of them in zip lock bags with plastic covers for the tie tag because that was supposed to make them more valuable if the little heart wasn't damaged.

I specifically didn't mention the teeny beanies when talking about the 1990s McDonald's Happy Meal toys 'cause I wanted to wrap that in here.

36:19

I spent a lot of money on fast food to get those.

I wonder if I could go back with them still in their package and like trade them in.

Can I trade in this elephant for 1/4 pounder with cheese?

So I have hundreds of these.

They're probably not worth much but they're still being made today so there could be a resurgence.

36:39

I'm going to keep my beanies till I'm like 90.

Maybe they'll be valuable then.

Then when they become valuable I'll go grab them out of the attic and immediately fall down the stairs and get killed on the weight trying to sell them.

There's the outlook of my old age.

36:56

Moving on.

Number 2 is NFTS non fungible token.

These are unique digital certificates stored on a blockchain.

Every one of them is supposed to be one-of-a-kind.

37:13

These were the most recent collectibles that everyone thought was going to be worth a ton.

The problem was all these NF TS.

It was the hype around what they could be worth.

You started to get scams out there.

There was a lack of legal copyright protections.

37:31

It is said that over 95% of NF TS eventually lost all monetary value.

The worst as far as NFT fails go was in 2021 when crypto investor Vignesse Sunderson hope I said his name right because he spent $69.3 million on an NFT.

37:54

It was the Beeple NFT every days the 1st 5000 days.

Reports vary but the $69 million for it.

This NFT is reported to be worth around $18,000 now, which is still a good money if you were just collecting.

38:14

Come on man, just imagine how many Beanie Babies you could have bought for $69 million.

Number 3 is Thomas Kinkade.

Prince Thomas Kinkade was an American painter known as the Painter of Light.

38:31

His paintings began to become popular in the 1980s.

While some of his original older oil works can still be valuable, he immediately went into mass production and commercialization of his paintings.

So you could have jumped in on this craze, buying these paintings thinking they were going to be worth thousands, 10s of thousands, only to see that he put out hundreds of thousands of copies of the same painting.

39:00

Good for him.

He ended up with a worth of almost $4 billion at his peak with how much money he made from these paintings.

But you started finding them discounted on QVC and that couldn't have been good for their resale value.

Like I said, the originals that he did, you could get somewhere close to $30,000 at auction.

39:21

But if you have one of the mass produced commercialized paintings, you're looking at 50 to $100.

You won't be finding these on Antiques Roadshow anywhere #4 are Franklin Mint items.

39:38

They're back.

The Franklin Mint brings back the cars of the 50s classics like the 57 Corvette, 56 Thunderbird, 59 Cadillac El Dorado 12 imported authentically detailed die cast dream machines in the classic 1 to 43 scale.

39:54

The Franklin Mint actually just made a comeback I guess.

I found their website.

They did a lot of products that were mass produced as collectors items in the 70s and 80s.

Figurines, collector plates, coins, medallions.

40:11

The funny thing is that you can still get money selling your Franklin Mint items.

But it's not for the items themselves, it's the resale values of the actual precious metals that the items were made from.

So if you had silver coins, people aren't going to buy them for the coins themselves, they're going to buy them to melt down the silver.

40:32

When you make a lot of things, mass producing them and then marketing them as investment opportunities, their value drops when people realize that all these other people have the same thing.

So they put them up on eBay and they get about 10% of what they paid for them.

But Franklin Mint is back, franklinmint.com.

40:51

That's what they say on their front page.

So there's a whole new generation of people that can go buy all kinds of things that could be valuable.

I'm sure if I'm still doing the podcast in 20 years, I'll look back at now when the things they're making is Investment Fails Part 2 and finally #5 on the top five collectibles that ended up being Investment Fails are Pogs.

41:27

Separately.

These were a part of my 90s teenage years.

Cardboard round tops that were decorative claim to be collectible.

The pogs, They were milk caps.

They got the name Pog from passionfruit, orange and guava juice.

41:45

It's a good thing they didn't start pogs with apple, strawberry and sour cherry.

Sorry, there's my teenage humor.

Pogs had their roots in Hawaii in the 1920s.

They were revived in Oahu in the 1990s to help teach math, and then they were globally commercialized by the World POG Federation, which I didn't know there was a such thing.

42:10

That's when you ended up with all kinds of characters all over the Pogs, Disney characters, Marvel characters.

You need to have a rare mint condition POG to get anything of value.

The majority of these Pogs today are worth between 5:00 and $0.25, but in rare cases you can get upwards of $100 for one of the officially licensed ones.

42:35

But like I said, rare mint condition.

But I'm sure most kids that bought Pogs in the 90s it was their allowance so their parents actually bought them so it wasn't really a waste of our money.

I kind of traded your soul to the guy at the comic book store.

42:51

But look, I got some cool pogs.

Alf pogs.

Remember Alf?

He's back in pod form.

But there you have it, some of the biggest investment fails that were masked as collectibles.

How many of these did you have or do you still have?

43:09

Should I ruin your day by telling you your NFT or Thomas Kinkade painting or any Franklin Mint items or Pogs were worth nothing?

Well don't worry because I have to be face to face with the Beanie baby so I'm suffering along with you.

43:25

I honestly thought around 2000 that I was going to have beanie babies that were going to pay off my house in the future.

Oh well, I'll wait another 25 years, maybe then they'll be worth something.

In the annals of history, there are some television shows that make huge impacts without lasting that long.

43:54

Shows like Freaks and Geeks, My so-called Life, Twin Peaks Police Squad.

All of those lasted one season.

But it's not limited to shows that lasted one year.

There are few TV series that have had as profound an impact on American comedy as Chappelle's Show and The Thing With Chappelle's Show.

44:17

It lasted for two full seasons between 2003 and four, and then a posthumously assembled third season released in 2006, Seasons 3.

The Lost Episodes was only three shows in total, with the final ever Chappelle's Show airing on July 23rd, 2620.

44:38

Years ago this week.

The show that aired on Comedy Central became a cultural phenomenon that permanently changed TV comedy, launched countless catchphrases into pop culture, influenced countless comedians, and transformed the creator Dave Chappelle into one of the most famous comedians in the world.

44:59

The irony is that the show's enormous success also became one of the primary reasons for its demise.

My introduction to Dave Chappelle came in 1996's The Nutty Professor that starred Eddie Murphy.

45:15

Dave Chappelle played Reggie Warrington, who was a comedian that Eddie Murphy went to see and when he was fat he got roasted by.

Before becoming one of comedy's biggest stars, Dave Chappelle had spent nearly a decade building a reputation as an exceptional stand up comedian.

45:33

He was born in Washington, DC in 1973.

He began performing stand up while still a teenager.

Throughout the 90s, he appeared on Def Comedy Jam, Late Show with David Letterman, Howard Stern, various other HBO comedy specials in addition to The Nutty Professor.

45:52

In the 90s, you could find Dave Chappelle in Robin Hood, Men in Tights, Conair, Blue Streak, Half Baked, You Got Mail.

Some of those movies were hits, some of them weren't.

But rather than chasing more film roles, which Chappelle wanted was creative freedom, a major turning point came when Chappelle partnered with comedian and writer Neal Brennan.

46:15

They had developed comedy ideas together for years, and their goal was ambitious.

Create a sketch comedy show that wasn't afraid to tackle race, politics, pop culture, stereotypes, celebrities, and uncomfortable social issues.

That was a big thing for me, watching Chappelle's Show as a white man from Cape Cod.

46:37

There were so many things that were so funny, but you'd also have this little bit of uncomfortableness while watching and listening to it.

It was kind of like, should I be laughing at this?

That was the point though, Chappelle's Show.

The point was, instead of playing it safe, they wanted to push boundaries every week.

46:56

Chappelle's Show debuted on January 22nd, 2003.

Let's start the show.

47:17

The show mixed several different comedy styles, but each episode kind of followed the same formula, with Chappelle opening with a stand up monologue, introducing film sketches, returning between the sketches, and ending with a live musical performance.

47:35

So it combined stand up sketch comedy, satire, fake commercials, music, television.

Unlike a lot of sketch comedy shows, the comedy almost always revolved around 1 central question on Chappelle's Show.

47:50

What if society's assumptions were taken to their most ridiculous conclusion?

Many of the sketches on the show began with relatively believable situations before becoming more increasingly absurd.

Naturally, the centerpiece of the show was Dave Chappelle himself.

48:07

He portrayed hundreds of different characters, different historical figures, news anchors.

He was Samuel L Jackson.

Black, George Bush, Lil Jon Dylan, Tyrone Biggams, Clayton Bigsby Other recurring people on the show included Donnell Rawlings, Paul Mooney, Neal Brennan who Co created the series.

48:31

But the biggest star on Chappelle's show besides Dave Chappelle himself was Charlie Murphy.

His True Hollywood Story sketches are some of the funniest things ever put on TV in my opinion and I'm sure a lot of yours that have seen the show.

48:48

If you have never seen the two sketches, I'm not going to do them justice, but naturally I'm going to go into both.

The most famous one is the Rick James one.

Tom Murphy What's up, partner?

Darkness, Everybody dark, Everyone.

49:04

Darkness is pretty.

That is in Season 2 Episode 4, which debuted on February 11th, 2004.

It has to do with various run insurance between Rick James, the R&B superstar and Charlie Murphy and Eddie Murphy in the early 1980s.

49:26

It includes Rick James destroying Eddie Murphy's new couch, punching Charlie Murphy in the forehead with his unity ring, the famous 5 fingers joke.

Charlie, that's a new joke going around.

Have you heard it?

What is the five fingers side of the face?

49:47

What slap?

Me and Charlie Murphy kicking him Kung Fu style and him flying through the air and smashing into a mirror.

What was crazy is they had Rick James actually on the show and him confirming some of these stories.

50:03

See I.

Never just did things just to do them.

Come on.

I mean, what am I going to do just all of a sudden just jump up and grind my feet at somebody's couch?

Like it's like it's, you know, something to do?

Come on.

I got a little more sense than that.

Yeah, I remember grinding my feeding at his couch, you know?

This might have been the last thing that Rick James ever did.

50:21

He died only a few months later.

I'm Rick James, bitch.

Then there was one that was just as funny and just as crazy, where it had to do with Prince and a game of basketball between Prince and his crew and Charlie Murphy and his crew shirts versus blouses.

50:41

And then after Prince dominates them in basketball, he makes them all breakfast with pancakes.

And Prince confirmed that this story was also true.

And he used a picture of Dave Chappelle dressed as Prince for the cover of his 2013 single Breakfast Can Wait.

50:59

Those 2 are my personal favorites and I'm sure probably a lot of yours.

They're not really that controversial characters in sketches like Clayton Bigsby, that's probably the most controversial because he's a black man who is blind, but he's also a white supremacist because he never knew he was black.

51:17

Tyrone Biggams, he was one of the most recognizable characters.

He was a crack addict, hyperactive personality with his random observations and constantly trying to find drugs.

You had wacky ones like the racial draft where they were drafting people like Tiger Woods, Colin Powell and Eminem.

51:38

The player haters ball where was characters competing to become the greatest hater?

Samuel Jackson beer, the take on Sam Adams where it's just all him swearing Jackson's.

Coming right out.

Good mother, of course, Jackson, made painstakingly by me, Sammy will Jackson.

52:01

It'll get you drunk.

You'll be fat girls in no time and.

Of course, Chappelle's impersonation of Lil Jon, the rapper, which helped to define his public perception.

The exaggerations of him saying what OK and yeah are.

52:19

You checking any luggage today, Sir?

And the backs have been in your possession the whole time?

What possession?

The whole.

Time you can see I'm trying to sprinkle in clips, but it's also I like to keep my show where you can all listen to it.

52:42

Not a whole lot of swears, but you know that Rick James 1, I had to have that in there.

One way that Chappelle's Show reminded me a little bit of In Living Color was him having musical guests every episode.

Now, In Living Color, it wasn't every episode, but they had a lot of hip hop artists and that helped to introduce them to a mainstream audience.

53:04

Chappelle's Show had people on like Kanye West, The Roots, Most Def Common, Talib quelli Erykah Badu, Cee Lo Green, Busta Rhymes, even John Mayer.

The show was a cultural phenomenon because it wasn't simply trying to be funny.

53:24

The humor behind things like racism, class, fame, media stereotypes, celebrity worship, police violence, it often forced audiences to question why they were laughing.

I know it made me question that.

The show received numerous honors Emmy nominations N double ACP Image Award recognition Television Critics Association praise.

53:50

Following the success of seasons one and two, Comedy Central reportedly offered Chappelle a contract worth around $50 million.

It was one of the richest television deals ever offered to a comedian at the time.

As production on season 3 began, everything changed.

54:09

In May 2005, Chappelle abruptly left production and traveled to South Africa.

Rumors were spreading that he was exhausted or that he was having trouble with substance abuse.

Chappelle later rejected a lot of these rumors, explaining that he was burned out, uncomfortable with aspects of the production environment, and increasingly worried that some viewers were laughing at racial stereotypes rather than understanding the satire.

54:37

That is why Season 3 of Chappelle's Show was only three episodes.

Dave Chappelle was not hosting them.

The episodes consisted largely of previously completed or unfinished sketches, and fans don't consider it a true third season.

54:55

I used it kind of as a jumping off point for this segment because it was 20 years ago this week that the last ever episode of Chappelle's Show, whether it was seen as a real one or not, aired.

Years later, Chappelle's Show became the center of a major debate over artists rights.

55:11

In 2020, Chappelle publicly asked fans not to stream the show because he said he was not being fairly compensated under his original contract.

Several streaming platforms removed the series while negotiations took place.

In 2021, Chappelle announced that he had reached an agreement with Viacom CBS, after which seasons one and two returned to streaming services.

55:35

Looking back, the show's influence can be seen across modern comedy.

Many later sketch series, including Key and Peele, borrowed its blend of cinematic production values, sharp social commentary, and recurring characters.

55:51

There are so many catch phrases and sketches that entered everyday conversations, and it demonstrated that cable TV could produce comedy with the same cultural reach as broadcast giants like Saturday Night Live.

Today, Chappelle's Show is widely regarded as at least one of the greatest sketch comedy programs ever made.

56:12

It helped to transform Comedy Central into a destination for original comedy.

It launched and elevated the careers of numerous comedians and performers.

It influenced countless more with sketch comedy writers and performers, created some of the most quoted and recognizable sketches in television history.

56:32

And this was all a show that lasted a total of 28 episodes. 20 years ago this week, Chappelle's Show aired its last episode, and since then, the series remains a touch tone for both comedians and television critics.

It helped to make Dave Chappelle, one of the defining TV stars of the 21st century, one of the best comedians of this century.

56:57

And for a show that lasted 28 episodes, its legacy is going to last much, much longer.

But until next week, that is going to wrap up episode 254 of the In My Footsteps podcast.

Thank you so much for tuning in.

57:12

Thank you for making it to the end.

I hope you have enjoyed this latest batch of Gen.

X nostalgia.

Whether you're on the beach, in some kind of AC filled room, or hopefully not stuck in traffic, the content train keeps rolling.

57:28

Next week we get into the month of August with episode 255.

Perfect for the heat of summer.

We're going to look back at the origins of sports drinks, Gatorade, Powerade, whatever else.

It's going to be story time as we take a look back at what it was like to live in the 1980s in summer.

57:49

You will hear me say a lot.

Things were better back in my day, but I'm just preparing you for it.

I say that, but we're also going to be looking at the top five 1980s TV show fails.

So not everything was better back in my childhood.

So that's coming up next week on episode 255.

58:08

Heads up, at the end of next month, beginning of September, there are probably going to be a few weeks that I may do mixtapes because as you know with the cabin filming, I'm going to be out on location.

It's not going to leave me a lot of time to create new podcasts and I don't want to rush 1.

58:28

I don't want to make a short one.

I'd much rather do something like a mixtape.

But don't worry, I'll be filming a lot of content while I'm on location, so you'll be getting a lot of stuff that I take in from my filming experience.

That stuff will probably be on Patreon first.

58:47

So if you want to get early access to all my behind the scenes foolishness on my filming adventure, join on Patreon tiers as low as $3 a month.

You're supporting me, my content, podcasts, books, blogs, videos.

59:04

You can also buy me a coffee.

Those are not recurring and they can be as low as a dollar, which really can't buy you coffee, but that's fine.

And also, once again, don't forget to check out the Cabin fundraiser.

It's right at the top of the podcast notes.

I had a really fun, unique, validating kind of time this week in checking comments on my podcast on Spotify.

59:30

I found a comment from someone and I'm not going to name their name, but if they hear this, they know I'm talking about them.

And they mentioned that they had been struggling with depression and finding my show and the content in it has helped them to deal with it.

59:46

They let me know that if I wasn't sure if my podcast mattered, to know that it did to them.

And I'm thinking to more of you.

I just don't hear it.

And it was something unexpected.

So I ended up sharing that sentiment on social media.

1:00:04

And I started to get more messages from more people about how not just my podcast, but my content.

Even my outlook on life has helped them or motivated them.

It really made all of this worthwhile.

1:00:21

I always loved doing these podcasts.

I love all the content I make.

I put so much work into these.

I've said so much.

I work a full time job and then I spend sometimes upwards of 1520 hours a week on top of that, creating, marketing, editing content.

1:00:39

I do all of this without any guarantees of success.

I guess it's kind of legacy building, leaving things that will be there when I'm gone.

It continued this week with my event at the Dennis Public Library.

I had specifically cousins coming just to tell my mother who was there how proud they were to be related to me.

1:01:05

I am not someone that goes out of my way to pat myself on the back.

I tend to either just stay quiet in the background or promote others.

But to hear such kind words from so many different people, many of whom I don't know, it made me feel like all of this work that's gone on for over 15 years has been a success.

1:01:27

I just wanted to make sure that I shared that and properly thanked everyone that reached out, Everyone that said such kind words, and all of you who might think these things but don't have the time to write me messages.

You all are the reason why I keep doing this. 254 episodes in 10 books, hundreds of blogs, hundreds of videos.

1:01:49

It is not work if you love what you do.

A very special birthday this week to my baby sisters, my twin baby sisters Lindsay and Ashley.

Their ages will remain redacted once you get over 40.

1:02:05

It's like OK.

I am so grateful and blessed to have you both in my life.

I hope the birthdays are the best they can be.

You get everything you want or at least have some good food and laughs.

I'm very proud to be your brother and I hope I make you proud to be my sisters with my foolishness that I do every week.

1:02:28

So happy birthday to both of you.

I love you and I'm sure I will see you soon if I haven't already by the time you hear this.

And for all the rest of you, there's still summer left.

We're just getting ready to start August.

Just remember, real summer doesn't end until the third week of September, no matter what magazines and TV commercials try to tell you.

1:02:48

And remember, in this life, don't walk in anyone else's footsteps.

Create your own path and enjoy every moment you can on this journey we call life because you never know what tomorrow brings.

Thank you all again for tuning in.

This has been the In My Footsteps podcast.

1:03:06

I am Christopher Centerland, you already knew them, and I'll talk to you all again soon.

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