For this all-new Working It Out Q&A, Mike fields listener questions about people fainting at his shows, how to write comedy about topics that are painful to you, and balancing a day job and creative life when starting out. If your question didn’t get answered on this week’s Q&A, stay tuned for another one soon where Mike answers the rest! Got a new question? Email workingitoutpod@gmail.com with a VoiceMemo asking your question.

Pete Holmes, a comedian and podcaster renowned for "You Made It Weird," joins Mike for a lively discussion. They punch up jokes before Mike's show, diving deep into the nuances of clean versus edgy comedy. A playful debate on puns unfolds, alongside reflections on the legacy of influential comics. Pete hilariously psychoanalyzes Massachusetts while Mike shares memories of opening for Tracy Morgan. Their candid banter blends personal anecdotes with cultural critiques, making for a delightful exploration of humor's many forms.

Nathan Lane, an acclaimed actor celebrated for his comedic brilliance, joins the conversation to share captivating stories from his illustrious career. He opens up about his collaborations with legends like Mike Nichols and Robin Williams, and reflects on the dynamics of friendship in comedy. Nathan discusses his emotional journey with his character in the upcoming Hulu series 'Mid-Century Modern', emphasizing the importance of taking risks in life and performance. The episode is a heartfelt blend of nostalgia, humor, and camaraderie.

Tig Notaro, a celebrated comedian and actress known for her candid and confessional humor, joins the discussion to share her unique insights. She hilariously recounts the time her brother fell into her stepfather’s grave. Tig opens up about the challenges of coming out as gay to her children, blending humor and heartfelt reflections. They also dive into the whimsical idea of a lesbian party bus featuring famous names. Expect plenty of laughs as they navigate love, family dynamics, and the humorous aspects of parenting.

Rory Scovel, a comedian and actor celebrated for his improvisational style, returns to share insights from his year-long journey of improvised stand-up. He reveals the emotional challenges of performing without a script and discusses his jealousy of fellow comedians' successes. Rory and Mike delve into how family dynamics complicate a comedian's life, balancing humor with vulnerability. They also explore crafting new jokes around complex topics, blending personal experiences with laughter, emphasizing creativity and adaptability in comedy.

Hasan Minhaj, a comedian and actor celebrated for his Netflix specials and work on 'The Daily Show,' makes a third appearance. He and Mike delve into hilarious memories of childhood crushes and athletic rivalries from school. They explore how comedy mirrors political cycles and the craft of joke escalation. Hasan shares anecdotes about his creative process, humor in crowd work, and unexpected incidents, all while keeping the laughs coming. Their camaraderie shines through as they reminisce about the past and discuss the nuances of storytelling in comedy.

Ben Stiller, a dynamic actor and director known for iconic films like 'Zoolander,' teams up with Adam Scott, famed for his roles in 'Parks and Recreation' and 'Severance.' They delve into the creative synergy that fuels their work on 'Severance,' sharing audition tips and how personal experiences have shaped their artistic choices. The trio reminisces about their early careers, discussing the balance of fame and identity, and the importance of genuine connections. Expect laughs as they unpack the art of directing and the power of empathy in performance.

Join a lively exploration of the struggle and joy within show business, as Matt Rogers shares his insights from writing for a hit TV series and auditioning for SNL. The significance of fun in the creative process shines through, paired with heartfelt reflections on friendships and industry challenges. A humorous debate on pop icons like Taylor Swift versus Michael Jackson adds a cultural twist. Plus, the hilarity of late-night cravings and the emotional depth of vulnerability and personal narratives brings a delightful mix of humor and introspection.

Stephen Colbert, renowned comedian and host, shares his comedic journey and invaluable lessons from legends like David Letterman and Mike Nichols. He reflects on the nuances of live performance versus television, emphasizing the importance of genuine dialogue and emotional connections with audiences. Colbert also candidly reveals what makes him cry and recounts memorable encounters with figures like George Lucas and the Pope. With humor and warmth, he highlights the beauty of improvisation and the significance of supporting charitable causes.

Rachel Feinstein, a vibrant comedian known for her Netflix special 'Big Guy,' returns to share her unique comedic insights. She hilariously reveals why her firefighter husband embraces her roast jokes and his quirky pronunciation of 'cash.' The conversation takes a wild turn as she recounts a chaotic road story involving Kevin Hart. Rachel also delves into new material about God getting sober and her funny experiences cuddling with a boyfriend at a spooky hotel. Plus, she advocates for supporting firefighters and their families.