Podcast Awesome

Clippy Cult: The Paperclip That Wouldn’t Quit

• Matt Johnson • Season 3 • Episode 18

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Inside the UX lessons, internet lore, and surprising comeback of Clippy

Love him or loathe him, you remember him. Clippy — the googly-eyed paperclip that lived inside Microsoft Word — has become a permanent fixture in internet culture. But how did a productivity tool become the patron saint of annoying-yet-adorable UI? In this episode of Podcast Awesome, we’re digging into the cult of Clippy with behind-the-scenes insights from Clippy's original creator Kevan Atteberry and Microsoft designer Sam Cundall. From meme fame to Microsoft Teams emoji, Clippy's legacy is more layered than you think.

📝 What We Cover in This Episode:

  • 📎 Why Clippy was loved and hated
  • 🧠 The psychology of nostalgic design
  • 🔁 When Microsoft secretly brought Clippy back
  • 🤖 What Clippy might teach us about the future of AI assistants
  • ✍️ thoughts on reviving legacy designs the right way

⏱️ Timestamps:
00:00 – Welcome to the Cult of Clippy
02:00 – The origin story: from helpful to hated
04:30 – Nostalgia and annoyance: why we love to hate him
06:00 – Microsoft’s secret Clippy emoji comeback
08:00 – What makes emoji design "work"?
10:00 – Fun at work: why weirdness builds culture
14:00 – The creator's take: Kevan Atteberry on designing Clippy
20:00 – From embarrassment to pride: Clippy's redemption arc
24:00 – Clippy vs. Siri: The rise of personality-driven UI
26:00 – Final thoughts: where personality fits in UX

🔗 Links & Resources:

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[00:00:00] Welcome to podcast Awesome. Where we chat about icons, design, tech, business, and Nerdery with members of the Font Awesome team. Well, it's just me here on another solo episode and uh, I'm a member of the Fun awesome team. My name is Matt and I'm the content guy and the host of this year podcast. And I'll be putting this podcast into the Nerdery category because today we're going to do a deep dive.

On the Cult of Clippy. Who's Clippy you may ask. Well, you know, back in the day when you were working in Microsoft Word and a little animated paperclip would pop up and ask if you needed tips with what you're trying to create.Yep. That, that's the clippy that I have in mind.

So why would I cover this? Well, you know, the Internet's already told clip's origin story a whole bunch. instead of adding yet another story, I figured we'd ask, why can't we seem to quit this guy? Why is Clippy still showing up in memes and sticker packs?

We just can't seem to quit Clippy. So let's rewind to 1997. A lifetime ago in internet yearswhen word art ruled and dial up was drilling that bing bonging nails on a chalkboard sound due to our brains.

And this was back in the day when home computers weren't quite ubiquitous yet and Microsoft was on a mission to make its office suite feel a little bit more intuitive and helpful, I guess. So at that point, Microsoft's office suite had been out for a few years, and when the 97 version launched, it included a delightful little affirmation, animation, a playful, googly-eyed, little paperclip guy with a bendy paper, clippy body, and uh, a whole lot of word processing optimism. [00:02:00] It seems like the big idea was that Microsoft was making a marketing push to show that their software was intuitive and helpful, and so love or hate him.

Clippy became a daily part of your work life. Were you writing a resume, drafting a formal letter, writing love poetry to our technological overlords? Clippy was there to support you with expert advice on how to make that document look super profesh. But let's say you were drafting something up that was a little out of the ordinary, or you were just taking down some notes and you didn't really need any formatting help.

Well, uh, then Clippy was, um, let's be honest, Clippy was a little annoying at that point. For some, he was a helpful little buddy, but for others he was an uninvited guest interrupting our workflow. He was cute. Yep. Absolutely annoying without a doubt. And it seems that Clippy was intended to provide humanizing user assistance, but maybe you remember how annoying it was when you were happily plunking along and.

Along comes clippy with a little popup that says, it looks like you're trying to write a resume and, uh, he derails your train of thought. So, as many of us may wish, Clippy had entirely died off nerd's. Collective consciousness just couldn't seem to quit Clippy.

It is like a chorus from a bad nineties radio hit that didn't age really well, that you can't seem to quite get outta your head. You know, the melody comes out of nowhere And so we wince, we roll our eyes and we groan. But come on, man, you know, you love it, but you hate it and uh, and you love to hate it

Smash Mouth: Hey, now you are an all star. Get your game on. Go [00:04:00] play. Hey, now you 

by 2021, it seems that some folks at Microsoft since this cultural ambivalence and brought clippy back as an emoji and the internet lost its ever-loving mind. For about, uh, roughly 36 hours. People were super stoked. Uh, Twitter exploded and then, then there was silence. And, uh, yet. Clippy still lingers like a mascot, haunting.

The code base clippy isn't really gone. He's just been fragmented and reincarnated across emoji packs and nostalgic Easter eggs forever popping up when you least expect him. And if you can believe it, it's been nearly three decades. Wow. Three decades and Clippy has taken on yet another life in internet folklore.

There are fan sites, tribute art and sticker packs and Microsoft teams to tell us a little bit more about Microsoft hinting at Clip's Comeback, I got a chance to catch up with Sam Conall? Kundal? ...  and here's what they had to say.

Matt: So at some point Microsoft did decide to re revive clippy and teams in emoji form. When that decision was made, you put a tweet out there, it kind of went viral.

 can you tell me the backstory of that a little bit.

Sam: so there was a hackathon, which we do every year and a design week, and one of those things was we were looking at changing our design language from, um, if you're Microsoft, uh. Nerd, like an MDL font to, um, this new fluent design, which is more three dimensional. You'll see the backgrounds and, and the splash screen.

I have the bloom on my, on my desktop and I can see it. And one of the, not just the icons [00:06:00] that we were changing, but we're also updating the emoji. And as we went through the set, we got to the, um, objects and symbols and we stopped at the paperclip. And that was the point where we went, this has to be clippy, it has to be clippy.

That nostalgia. Yeah, we're discussing about how to do it and just to validate it, this tweet that we put out, From Microsoft, we wanted to get, what was it, 20,000 likes or something? Um, it got 140,000. Uh, so

Matt: so great.

Sam: I think that's good validation to say we should do it. you know, we just stumbled across

what do people want? Well, let's just embrace it.

Matt: Yeah, absolutely. I was talking to another designer, uh, in recent weeks and he creates toys for his studio just for the joy of it, you know, and, and does like limited runs of it.

And, and so we were talking about nostalgia

maybe this is a big question, but how do you think about that idea of nostalgia and then the functionality alongside of that in design?

Sam: Um, there's a blog, Dilbert blog that talks about writing funny, uh, which says, if you can hit a few of these items, like cute, uh, recognizable, clever, uh, and these different items, then you're starting to like tap into something that people. Can not only just use once, but they can use many times in different conversations.

And I think that's the key to a really successful emoji. And clippy expressed that through this sense of a bit of a deadpan face or an expected face through just [00:08:00] ease a paper clip. You know, he is used for holding pieces of paper together. You know, that's a real functional thing, but it's got this personality, which is more hopeful.

That nostalgia connects to the human need of like. I remember this. Do you remember that? So when we're adding these little flares, you know, what are we doing there?

When I create emoji, it is about, uh, the accent of that message and being able to give more meaning to go beyond just that's a.

That's just saying I'm happy, you know, I'm sad I'm, but it's like sometimes you lose the context of the conversation. You know, so you can just really, you know, form those fun personality traits and connects with other people. 

Matt: Was there a feeling among Microsoft that you could kinda get a temperature for?

Like people are like, oh, this is so funny, this is gonna be great. Or, oh boy, you know, like a lot of eye rolling.

Sam: We were looking at ways that we could bring Clippy back and so, you know, that was something that the sentiment around our company was sort of growing in excitement as we sort of suggested this idea of clippy in the emoji set

Matt: so how, how do you think about balancing, um, that sense of playfulness and like a, a productivity tool like teams?

Sam: it was there to be able to express more clarity and we need to do that in our now hybrid work environment. It's like, how do we help people bring more clarity?

 we need to have this variety that resonates with different people so that.

 there are different scales or temperatures of, of feelings. So, [00:10:00] you know, data shows that fun at work, um, helps in so many ways. It helps people be productive, it helps connection and it brings a better culture. And so, you know, I really feel that we need to help everyone feel included. So yeah, the quirkiness helps people share, um, makes people feel connected. 

Matt: Absolutely. that's one of the drawbacks of remote work is that you're not there with that person. You don't see, you don't see facial expression, tone of voice. If there's ways to sort of share a semblance of that, then you're still, you're keeping that connection, you're keeping that human aspect, um, to the rhythms of works, which I think is really important.

Sam: Totally.

You know, having something that we both share now that could be a gif that has something from say the Office or from Monty Python or from Minions, you know, that really like, oh my gosh, I remember that from that film. 

Matt: So do you think that there's ever gonna be a time where Clippy will actually be a real, real assistant in the future and not just a sticker?

Sam: Okay. You know, I'm gonna say Microsoft Line. There is no official plans to bring him back, uh, but. It definitely remains as a popular internal joke. If you, if you come and work at Microsoft on the NEO day, um, then there is definitely a figure of clippy or someone dressed up as clippy. Um, and so, you know, the fans are still there.

 Uh, actually you have seen some Easter eggs of, of like could clippy be an assistant and when we talked about Microsoft copilot, I was actually [00:12:00] asked the day before the announce, hey, could you just. Put a little blink on clippy.

It was all shush, shush. So I didn't know what it was for, and I was like, oh, we don't have that. Oh, and just, oh, just add it. I'll just add it. So, uh, in my sort of hacky way, I took the smiling face, I removed the yellow, I took the eyes, I found the clip emoji, I put the eyes on top and masked out and sent it.

And. That was it. They were like, oh, that's great. Next day there's this announce with you, Yusef at Microsoft Copilot, and he goes, we've got, someone can help with talking about copilot. And there he pops up on the screen and I'm like, oh, what? Oh, oh my gosh. I did not know that what I was doing the day before was gonna be for the the announcement.

Yusef: do you have a favorite video game character, for example, like Spiro. Or perhaps some people in this audience might want something a little nostalgic. Woo,

Sam: So I'd say. Not officially, but it's there on the side. Just like, you know, playing along with the idea. So

Matt: You nev you never know. You never know. Maybe, maybe someday. I love that.

Do you have any advice for, um, that you'd give to somebody that's trying to revive an old design or a mascot, um, in a way that lands, you've been through this experience now, it's been a couple years, uh, what would your advice be for somebody?

Sam: Simon Sinek is a great, um, podcaster does a thing called, a bit of optimism on Spotify. my point to Simon Sinek is he came up with the why.

simon sinek: very few people or organizations know why they do what they do.

And by why I don't mean to make a profit. That's a result. It's always a result. [00:14:00] By why, I mean, what's your purpose? What's your cause? What's your belief? Why does your organization exist? Why do you get out of bed in the morning? And why should anyone care?

Sam: The way the businesses work are like the why, the how, and the what. And it's so easy to fall into the what, like, I'm gonna make this, but really knowing why's so important and, and so if you ask yourself that question, but I wanna layer on one more thing, which is like, yes, there may be a why, but. Also marry that with your personal brand.

What brings you joy, meaning value to your, to your life? What are you doing that you feel that is you? So if you can take that why and your personal brand and bring it together and it and it works. Say for example you do like a, um. A blog before you start the project. That's another approach you can do.

And if that blog sounds really interesting, then you're onto something. If it sounds like I'm changing the radius of a corner, you know, uh, then maybe not. You know, you may have to do it, but you're not gonna sort of shout about it. So yeah, I would, I would add that personal branding to the why, and you'll be onto something. 11:30 ET / 10:30 CT / 8:30 PT

How do I get rid of what? Ah, we invented this stupid paper clip. Design some characters for a project called Microsoft Bob, That'd be me.


And after his creation of clippy with Microsoft back in the nineties, Kevin has since become a children's book illustrator for books like. Bunnies. I want a boat and I love you more than the smell of swamp gas.

Matt: I was kind of looking over sort of the history of, of all the clippy stuff [00:16:00] and, um,it's funny to see the fandom around it and the nostalgia and, these niche things 

Kevan: Yeah, I mean, he's really come into his own in the past, say, 10 years just on, he's adored as much today as he was held in disdain when he was in the, in the product.

Matt: When I talk to folks, it's sort of this feeling of. Oh man, it was so annoying. You know, all I was wanted to do is just jot down some notes or I was trying to do something simple in Word and lops this thing and I had to figure out how to disable it, and it's so annoying.

Um, but then when you recall it again and you have a conversation Oh yeah, I remember that thing. even if it was a little bit of a flub on Microsoft's part, it's sort of draws people in, you know?

Kevan: Yeah. Well, it's, it's a, it's, it's a, it's a shared experience with everybody. 

Matt: I think I came across something at some point that said, Clippy tested well, initially, but then wasn't received very well. Do you remember that at all?

Kevan: Oh, yeah, yeah. I do. I remember that. we had these, a couple of, uh, social psychologists, here for, uh, six months uh, clippy kept testing really well in likability and, uh, trustworthiness and, intelligence and eventually he became the default character because people liked him and, and you know, as a static image, he's really kind of engaging, but there was other people, that really.

Were not happy with the choice and, developers were more, oh, you can't have a stupid paper cliff. And, you know, and, and my, I was just, well, that's what they chose. Had I known how, what a big deal.

He would be eventually, if I had known, I would've treated, you know, obviously treated it a little differently. But I would never put Clippy in my portfolio 'cause I was kind of embarrassed about him because, um, people did not like him. People, you know, [00:18:00] had really strong negative feelings about him.

Um, until I, I realized that, you know. Press is good press. And I saw it on a client's computer one time and, and when I was at, uh, at her office and I guess said, oh yeah, I created that. And she goes, oh my God, that is so cool. And so, oh well, yeah, I guess it is. Cool. Um, and then I realized that, you know, like I said, that no press is bad.

Press us.

 I just, uh, I just embraced him and, uh, and then I would use that. I, I would say, this is one of my bigger things is I created clippy. And, um, over the years, uh, I tell you, he opened a lot of doors for me. I got in to see people that I, I may or may not have, uh, without him, but the, the notoriety of it is, was, was really valuable to me.

It's still really valuable to me. I mean, it, a week doesn't go by when, when somebody doesn't send me or, or 10 people don't send me the latest clipping meme, you know?

Matt: Oh, that's funny. Yeah. And it like pops up in, uh, TV shows and people make these like, drop these little references. It's like, yeah, it's, it's a shared experience across the board, you know?

Stewie: Once they're under my control, the entire world will be subject to my whims. Go wear your paperclip. No one likes you. 

Matt: At Microsoft I did get a sense that there were like kind of these.

Competing voices of like, oh yeah, this is great. but then there were, like you said, maybe developers that were like, I hate this. I don't, there, there were like internal code names or like acronyms

Kevan: Yes.

Matt: words where people are like, I hate this thing.

Kevan: everybody says that bill referred to it as that fucking clown. Um, and it's a funny thing because, Clippy came out of, uh, Microsoft, Bob, which was, um, [00:20:00] Melinda's, big project at the time.

And, um, 

Matt: Yeah. So maybe he's like, well, she likes it. I, I don't know. It's like one of those things on our product.

Kevan: I dunno either. I don't know how all the big money works around you.

To me, Clippy is, a really, uh, interesting and likable character. I always would, was kind of an Apples product guy and 

I never actually saw him in action. I did not know how, people respond to him. And so when he got just all this horrible press about, how annoying he is and everything. It was, it was embarrassing,

Matt: Hmm. Yeah. Yeah, that would, that would be tough. I also had that shared experience of like, this is annoying. Like, how do I turn off this notification

Kevan: Yeah.

Matt: Looking back on it, the, the, the way that you set up the animations it was like, that's really cute.

That's delightful. Especially given, um, probably the constraints that you had with the tools that you were using. I mean, that, I'm sure that would've no small task to do that.

Kevan: Yeah. Yeah. Uh, just to be clear, I would like to say that I did not do the final animations on 'em. Um, I, uh, I, I designed a bunch and then, a friend, uh, named John, Michelle did the, I believe, did all the animations and he did a

Matt: Oh, I see. Mm-hmm.

Kevan: uh, you know, I were based on, on the stuff that I designed as, but, uh, yeah, he did a really great job. 

Matt: Can you remember back when. working on this, uh, project, like, what was the feeling at the time when you were creating it? Did you had to have a sense that it would get legs or, you know, what it would become 

Kevan: I think we had about 250 or so character designs that was all whittled down to Clippy. Um, and I had about 26 in them. The honest to God truth.

That was the very, we, we were, you know, given the assignment, let's go design characters. The very first character I, I drew was Cliffy. we were moving from Bob, which was a home environment to office, which is, business environment. But, and so, you know, I just said, okay. I started looking, you know.

[00:22:00] What's an office thing? What kind of character would be in an office? And I, the first thing I did is I drew a paperclip and I thought that was hilarious. This was all a lesson learned for me from. taking a job se seriously, or not seriously? Not that I didn't take it seriously. And then back at the time I just was my own vendor. Clippy taught me that, that, you know, to take, take things a little more serious.

Everything you do, it could, who knows what it's gonna turn 

so Clippy wasn't just a productivity feature, he was Microsoft's first real attempt at personality driven design. And uh, it raises a bigger question, how much personality do we actually want from our tools? come on, you gotta hand it to clippy. He was trying his darnedest to be contact to wear. Looking over your shoulder. A little creepy maybe. and like clockwork, he'd pop up with related help tips even when he didn't ask. So while Clippy was based on developing albeit shallow pattern recognition, now the world of AI based on large language models can better understand context to generate helpful answers or code and text on demand.

We should at least recognize that Clippy did have a vibe. He wasn't just a tool. He had a face, he had expressions. He had a sort of faux personality. Clippy may have been basic, but Clippy walked so that Siri could tell you a joke.

Have you heard the joke about margarine? Nevermind. I better not tell it.

Alexa. Alexa could develop a personality Chat, GPT could banter and replica could simulate emotional relationships.

Uh, is it just me or is that a little bit creepy? Huh?

So for me, Clippy brings up some questions about adding personality to digital tools. How do you balance inserting an emotional tone into an interface while staying functional at the same time?

Clippy may have [00:24:00] been charming, but where do you draw the line between charming and annoying? Since the days of clippy design has come a long way and minimalism, subtlety, and opt-in help make for a better user experience in general, but. In the end, maybe you could make the argument that, uh, clippy unintentionally inspires better design through bad design.

 just think of Clippy had today's AI machine learning and natural language processing. Undoubtedly, there's already somebody bringing together the very best of clipping nostalgia with the sophistication of today's ai. Everybody loves some well trained novelty, I mean. I, I mean, at least I do. Even if you're not knee deep in UX wire frames all day,

It's easy to see how design intent doesn't always equal user joy. Thanks to Sam Cundall and Kevin Atterberry for giving us the scoop on the background for Clippy, and thanks to. Clippy himself. Clippy, clippy herself, Clippy, clippy themselves. Thanks Clippy for all of the nostalgia, the great fond and irritation Podcast Awesome was produced and edited by this guy right here, Matt Johnson. The Podcast Awesome theme song was composed by Ronnie Martin. The music interstitials were done by Zach Malm and the video editing for these video episodes, we get a little extra help from Isaac Chase.



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Matt Johnson

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Jory Raphael

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