Initially conceived as a show about the humorous side of addiction, specifically excluding stories about recovery, the focus has changed over time, especially following Chris' relapse and overdose death in July 2018.

As of 2019[update], Dave hosts the show alone, with occasional celebrity guests notably Jamie Lee Curtis, Dr. Drew, Brandon Novak, Fentanyl Jay, Ray Brown, and Brian "Hottwheels" Connolly.

[1][3][a] Dave worked at a Jewish deli in Manhattan, while Chris managed a sober living facility while studying for postgraduate degrees in psychology.

[2] As the show grew in popularity, it reached 40,000 monthly downloads and a fan base they termed "Dopey Nation".

During the podcast's 100th episode, Chris had jokingly speculated about one possible way the show could end: "One of us will get injured and get pain meds and take them while doing Dopey.