Still Building the Room

I did a quick Google search on the legend himself and landed on a 2011 interview that gave me some great insight into Cleveland Jackson. One detail stood out immediately: he did his first stand-up set in March of 1996. For reference—and purely to keep things light—I was born in August of 1997.

Sorry, Unc.

What that timeline really shows is perspective. Cleveland has been doing comedy longer than some of us have been alive, yet he carries himself with humility, enthusiasm, and a genuine love for the craft. There’s no ego—just respect for the room and the people in it.

Cleveland has always been a huge advocate for local comedy scenes and understands how those rooms fit into the larger nationwide comedy world. In a time when it’s common to see comics gain success and disconnect, Cleveland remains one of the most welcoming and invested comedians I’ve ever met. He watches sets, encourages growth, and treats every comedian like they matter—because to him, they do.

One quote from that interview stood out more than anything else. When asked what the best advice he had ever received was, Cleveland said: “It gets better, but it never gets any easier.”

That line hit home. It’s something I’ve been unconsciously living by in my own comedy journey, and hearing it echoed so clearly by a veteran like Cleve made it feel even more true.

That philosophy is on full display every Tuesday at Mr. G’s Bar and Grille in Middletown, where Cleveland runs the weekly Behind the Bar open mic. The comic stands dead center in the room with the full attention of the crowd—no hiding, just honesty. It’s one of the most unique and valuable mics in the Louisville comedy scene.

Beyond the weekly mic, Cleveland also brings monthly showcases to Mr. G’s taproom, featuring nationally touring comedians. He’s also expanding into the podcast space with the Sunday Social Podcast, recorded at his homecourt—Mr. G’s (where else!). You can find the most recent episode linked here, and be sure to follow Cleveland on Facebook for everything circulating in his world.

Cleveland Jackson is proof that longevity in comedy isn’t about surviving—it’s about showing up, evolving, and keeping the room better than you found it. Comedy needs people like him, and luckily, he’s still right here building it.