What happens when an insurance salesman walks into a comedy club on a dare, gets hooked on making people laugh, and eventually becomes the World Series of Comedy Grand Champion?

You get Rob Coleman.

On this episode of The Bar Gig Files, I caught up with Rob Coleman, the 2025 World Series of Comedy Grand Champion and one of the headliners on The Pub & Grub Comedy Tour, to talk about winning comedy competitions, working neighborhood bars, surviving the business, and why the future of stand-up comedy might actually be found in its past.

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

He got interrupted by hunting photos, a flying leg kick, and fake boobs -- now Bar Comedy USA Superstar, Dewayne White calls bar comedy "combat comedy."

• Why Bar Comedy Makes Better Comedians
• The Bar Gig That Sounded Like a Reality Show Nobody Would Greenlight
• The Hardest Comedy Audience is Not Always The Mean One
• Clean Comedy is Expert Mode
• From Army Veteran to Comedy Teacher