Bay High grad returns to Cleveland to headline at Hilarities

BHS grad Rob O'Reilly will be headlining at Hilarities Comedy Club on July 2, 6, 9 and 13.

When Rob O’Reilly graduated from Bay High School in 2003, he had a dream of becoming a stand-up comedian. So, he went off to Boston University to study communications and began to do stand-up at Boston venues – for free – just to get the stage time.

Since then, Rob has had appearances on "The Tonight Show" as Jay Leno’s correspondent, NBC’s "America’s Got Talent," and Comedy Central’s "Live at Gotham." He was named one of LA Weekly’s Top Ten Comics to Watch and has performed at over 300 colleges. Now 29, Rob currently lives in Los Angeles and is in his third season working as writer for the hit MTV show “Ridiculousness.” 

In July, Rob will be returning to Cleveland to headline at the comedy club Hilarities, which is downtown on East 4th Street – an upscale comedy club that is located in the basement of Pickwick and Frolic.

Rob always had an interest in comedy. “When I was about 4 or 5, I was at a Toledo Mud Hens minor league baseball game, and the mascot pulled me down on the field," Rob said. "He asked me to kick him in the butt when he turned around. I did so, he fell down, the crowd went wild, and I became hooked on making people laugh. I was voted class clown in the eighth-grade yearbook. Then, during my sophomore year, my Spanish teacher, Mrs. Rule, encouraged me to put something together for the high school talent show. I didn’t have enough material yet, but I started writing jokes. When the talent show came around during my junior year, I had 5 minutes prepared and performed at that for the first time.”  

Rob acknowledges that the transition from a high school talent show to a career in stand-up comedy is extremely difficult. “Beginning a stand-up career is honestly the hardest thing I’ve ever had to do. There are many nights where you question not just whether you’re any good, but whether you are sane. You’re caught in a Catch-22 where you need stage time to become funny, but nobody will give you stage time because you’re not funny yet!”

However, now Rob is really enjoying his career. “Now that I’m over that hump, it’s super easy and fun pretty much all the time. People pay me to tell jokes. It’s the best!”

Rob writes all of his own material. When asked how he comes up with new jokes, he chuckles. “Usually I’ll observe something weird or someone will say something I think sounds dumb, so I’ll make fun of them in the moment. Then I’ll write it down in my phone. Later on, I’ll think about all the even funnier things I would have said if given enough time to brainstorm. Generally this involves creating an analogy. So the joke becomes, ‘this weird thing happened, that’d be like this other even weirder thing’ or ‘imagine if this even weirder result had happened’. I’m not sure if what I’m saying makes sense, but that’s the nuts and bolts of it.”

Rob has plans to continue doing stand-up comedy and hopes to become a writer for a network sitcom. You can see him at Hilarities on July 2, July 6, July 9 or July 13. The shows start at either 7 or 8 p.m. Tickets are $13 or $18 and can be purchased in advance at

Read More on Arts & Entertainment
Volume 6, Issue 13, Posted 9:20 AM, 06.24.2014