In the season one finale, Jack is interviewed by his mother and aunt. They remind him how difficult he was as a child and when he was using, and Jack airs some grievances. Jack's mom recounts the times she had to pick him up from jail and admit him to a psych ward. Past guests call in too. And ... Jack interviews his late best friend, John Cibula.

"Public Servant of Cinema" Kathy Del Beccaro speaks with Jack for the first time in five years about how an article he wrote about her negatively affected her. They recount the unique relationship they had when they were both active alcoholics, and discuss whether or not they

can reignite their friendship as non-drinkers. 

Actor-singer Jessie Pinnick challenges Jack as to why he needs to make hyper-personal work at the expense of his personal relationships. She also talks about finally being able to take herself seriously as an artist, getting over self-loathing, and some of her and Jack's worst fights as collaborators.

In lieu of a proper episode, enjoy more of Jack's conversation with writer Laura Albert a.k.a. JT Leroy. Laura speaks on the backlash she faced after being outed for not "really" being JT Leroy, gender fluidity, and how to politically activate people through art. Jack will be back with a regular episode next week.

Actor-comedian Mike Cullen joins one of his oldest friends, Jack, to discuss how Jack used to be a bit "dramatic" for his taste, the obstacles of trying to make it in L.A., depression, food addiction, receiving sage advice from Bob Odenkirk, and working with the late Biff Wiff. Check his hilarious videos out at @mikeccullen and his album Red Rings of Death (under the stage name Airball Mike), coming soon.

Actor-comedian-filmmaker-dancer Eleanore Pienta and Jack bond over having dead dads. Eleanore also opens up about the societal stigma she faces for dating a man her dad's age, and why she makes things. Visit Eleanore's website, https://www.eleanorepienta.org, for all things Eleanore.

Ena Da, a.k.a. @park_slope_arsonist, is a comedian, digital creator and viral sensation. She speaks with Jack about the pros and cons of social media, growing up in Ghana, sexual mismatches, and how we survive a digital landscape controlled by oligarchs. Follow her on Instagram, Tumblr and Twitter/X.

Music legend Loudon Wainwright III speaks with Jack about the consequences of autobiography, wanting to connect with his children, being tagged as the new Bob Dylan, and whether or not there is hope. Check out his new album, Loudon Live in London, today.

Singer-songwriter-actor Hal Baum speaks with Jack, his oldest friend, about self-harm, depression, his musical influences, and what it was like to watch their mutual friend, the late John Cibula, slip into drug addiction.

Caveh Zahedi returns to talk about his sometimes-turbulent relationship with his late friend, D. Montgomery, who founded the Austin Film Society along with Richard Linklater. She was also in Linklater's Slacker and Caveh's I Don't Hate Las Vegas Anymore. Jack and Caveh discuss what it's like to have a friend who struggles with alcoholism, and how helpless one feels when there is nothing you can do to help. This interview was recorded in 2022.