The Bar Gig Files with Guest, Skyler Bolks "Tall Tales and Bike Trails"

The Bar Gig Files

The Bar Gig Files
The Bar Gig Files with Guest, Skyler Bolks "Tall Tales and Bike Trails"
Jul 13, 2026 Episode 10
Jeremy Danley

 What happens when a 6'7" comedian, a 1,000-mile bicycle tour, and a lifetime of Midwest stories collide? 

Skyler Bolks, headliner on The Pub & Grub Comedy Tour, talks about life on the road, performing in neighborhood bars across America, writing razor-sharp one-liners, and the surprising inspiration behind his Jokes & Spokes bicycle comedy tour across South Dakota. 

Along the way, Skyler shares hilarious travel stories, behind-the-scenes insights into the life of a working road comic, and why some of the best comedy crowds you'll ever find are in small-town bars.

Whether you're a comedian, bar owner, or just love hearing what really happens between the gigs, this episode is packed with laughs, road wisdom, and plenty of Midwestern charm.

Topics include:

  •  Touring the country as a full-time road comic 
  •  Performing in bars vs. comedy clubs 
  •  The art of writing great one-liners 
  •  Skyler's 1,000-mile comedy bicycle tour 
  •  Life as one of America's Best Bar Comics 
  •  Why small-town audiences are some of the best in comedy 

Grab a drink, pull up a barstool, and enjoy another behind-the-scenes conversation from The Bar Gig Files
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