How Ben Gleib Reinvented Late Night on YouTube, Went Viral in Political Debate, and Helped Save Comedy During COVID

About this episode

Ben Gleib discusses his journey in comedy, including his viral political debate and the creation of a new late-night show for YouTube.

How Ben Gleib Reinvented Late Night on YouTube, Went Viral in Political Debate, and Helped Save Comedy During COVID Hosts Sarah J. Halstead and Rich Chassler welcome comedian, creator, and disruptor Ben Gleib for a fast, funny, and surprisingly thoughtful conversation about career pivots, political courage, crowd work, and building comedy for a new era. Ben opens up about overcoming a childhood speech challenge, creating connection through stand-up, and why he's always pushed beyond the expected lane. The conversation moves from live comedy and dating confidence to the deeper purpose behind making people laugh. This episode also dives into some of Ben's biggest career swings, including his viral Charlie Kirk debate, the launch of Nowhere Comedy during the pandemic, and his newest ambition: Good Night with Ben Gleib, a digitally native late-night show built for YouTube. It's a sharp, hilarious look at what happens when a comic combines talent, activism, and entrepreneurial instinct to build what traditional entertainment wouldn't hand him. Guest Info Ben Gleib is a stand-up comedian, TV host, and creator known for sharp crowd work, high-energy storytelling, and building projects…

People in this episode

Hosts: Sarah J. Halstead, Rich Chassler

Guest: Ben Gleib

Topics covered

• late night comedy
• YouTube
• political debate
• COVID-19
• career pivots
• crowd work
• comedy activism

Keywords

• Ben Gleib
• late night
• YouTube comedy
• political courage
• crowd work
• Nowhere Comedy
• COVID-19
• comedy career

Mentioned in this episode

Organizations: Nowhere Comedy

Books & works: Good Night with Ben Gleib, Idiotest

More episodes of Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

• Bob Kushell on The Simpsons, Stand Up, and Starting Over in Hollywood · June 1, 2026 · 59 min
• Danny Farber on Vertical Filmmaking, Platform Strategy, and the Future of Storytelling · May 25, 2026 · 59 min
• From Teen Dad to Touring Comic: Willie Macc on Pain, Parenting & Punchlines · May 19, 2026 · 53 min
• Laurie Douglas on Comedy, Social Media, and Why Art Should Make People Uncomfortable · May 11, 2026 · 55 min
• Fizaa Dosani on Going Viral Without Selling Out | Comedy, Culture & Mental Health · April 27, 2026 · 57 min
• From ChoCo Krispies Commercials in Colombia to Netflix Is A Joke Fest: The Brittany Ross Story · April 20, 2026 · 49 min