Writer-director-actor Alex Heller (The Year Between) talks with Jack about the dangers of being labeled "gifted" as a child, her mental health struggles, being misprescribed Adderall as a teen, working with Steve Buscemi and J. Smith-Cameron, and social anxiety. Watch out for her new short film, Debaters, which will premiere as part of the 2025 Sundance Film Festival.

Writer-director-actor Madison Hatfield talks with her festival buddy, Jack, about embracing kinks, learning to advocate for oneself sexually, being a sub vs. being a dom, and her divorce. Watch out for her short film, I Could Dom, which will be online soon.

Jack wishes you a happy New Year and tells you about the first time he got arrested.

Jack wishes you a happy holiday and tells you about the time he ruined Christmas.

Musician-actor Hannah Lee Thompson speaks with Jack about night-eating, her musical origins, being ostracised from her community, and her ongoing struggles with depression and weight management. Check out her feature debut, the Slamdance-winning Hannah Ha Ha (which Slamdance also gave her the Best Actress award for) and listen to her songs wherever you stream music. Follow her on IG @banjohannah for updates on her upcoming shows and music!

Actor Colleen Rose Trundy and Jack discuss the challenges that face their relationship, namely their sex life. Colleen opens up about her complicated relationship with her own sexuality, the effect that Jack's cheating had on her (as well as him discussing it publicly) and how annoying Jack's bathroom habits are.

Writer-director Alexandra Qin speaks with Jack about infidelity (on the heels of him stepping out on his own relationship), her journey from tech to filmmaking, her need for excellence, and life as a recovering alcoholic, workaholic, and sex, love and drug addict. Check out her short film, Thirstygirl, now: https://vimeo.com/alexqin/thirstygirl

Animator/video guy Joe Cappa opens up about depression, social anxiety, finding inspiration in things he hates, and the importance of not overthinking things. Look out for his new series, Haha You Clowns, coming to Adult Swim soon.

Legendary filmmaker Caveh Zahedi speaks with Jack about their complicated mentor-mentee relationship, seeking revenge through art, and his unique views on morality. Check out Caveh's The Show About the Show, wherever you can find it.

Writer-filmmaker-actor Sofia Banzaf talks with Jack about Kratom addiction, “slut recovery,” the cost of autobiographical writing, and the need for drama to create art. She also helps Jack navigate a budding romance of his. Check out her book Pony Castle, wherever you get books.