Let's Talk About Sets!

The delightful charm monster, Patrick Holbert, joins us to pick away at PAIN in stand-up comedy. We talk about how pain is the source of much of stand-up, both physical and emotional, and how usually the audience needs to know that the pain is ultimately “ok” in order to laugh. We cover generational pain, the occupational hazards of talking about pain, how to refocus personal pain onto a “shared” experience rather than just making it about you, and how Patrick went about talking about his painful experiences the first time. It’s a fun talk with old friends about a major element of comedy as a whole, and stand-up in particular, which we trace through a few key bits from Patrick’s own material and a seminal late night set by Gary Gulman.

The "illustrious" Jay Jurden gayly talks about gay humor and also humor about gayness in this episode where we examine the relationship between stand-up comedy, homosexuality, and homophobia, tracing a path from Richard Pryor to the present.

Roy Wood Jr., Daily Show correspondent and stand-up comic, shares how he researches and builds risky, perspective-driven jokes. He talks about flipping morals for laughs, pacing complex premises, turning confrontation into material, and the roadcraft of testing and organizing sets. Expect stories about courting outrage carefully and creative hacks he used to get ahead.

LeClerc Andre, stand-up comic and writer seen on The Tonight Show and NBC's Bring The Funny, breaks down callbacks and comedic structure. He analyzes Patrice O'Neal and Moshe Kasher bits, explains timing, repetition, and when callbacks become powerful or cheesy. LeClerc shares his visual notebook method, rehearsal habits, crowd-work tactics, and why callbacks build instant in-jokes with audiences.

Steven Rogers, stand-up known for clean, self-deprecating material and TV spots, performs and breaks down tight, misdirected bits. Short clips spark talk about implied filth, “I know I look like” jokes, and making clean language sharpen absurdity. They also dissect Late Show with Stephen Colbert prep and stagecraft.

Steven Rogers, a clean observational comic who has opened for Brian Regan and appeared on The Late Show with Stephen Colbert, joins to discuss clean stand-up. He talks about adapting to theater crowds, following a headliner’s tone, why clean comedy reaches wider audiences, and how constraints can sharpen writing.

Bret Raybould, stand-up comic and sketch creator known for fearless stage work, talks stage presence, being present, flow state, pacing, silence, and resetting a room. He shares touring stories like following Leslie Jones and how knowing your act frees you to riff. Conversation highlights using universal road bits, eye contact, and when leaving the script can win a crowd.

Gastor Almonte, Brooklyn-born stand-up known for his Comedy Central “Brooklyn Batman” tale. Jeff Simmerman, award-winning NYC comic and storytelling teacher who maps a five-point comedic formula. They explore building stories from need to return, using surprise twists, vivid sensory detail, vulnerability over one-liners, structuring long tales, and practical editing and rehearsal techniques.

Usama Siddiquee, a stand-up comic known for observational, character-driven material, returns to break down contrast in comedy. He discusses playing naive personas, crowd-work games, satirical flips, and uses clips from Bargatze, Schulz, and Demetri Martin. Expect talk of delivery, tonal swings, and how contrast fuels laughs.

Jackie Kashian, stand-up comedian and Dork Forest creator, shares her Wisconsin roots and knack for longform storytelling. She talks about turning painful family moments into funny bits. She explains balancing poignancy and humor, respecting real relationships onstage, and mining specific details to make stories universal.