HBO and The Ringer’s Bill Simmons is joined by comedian and star of HBO’s ‘Crashing,’ Pete Holmes, to discuss his start in comedy, his favorite conspiracy theories (11:00), why roasts are therapeutic (22:00), the art vs. the person (28:00), the premise behind ‘Crashing’ (33:00), New York’s stand-up scene (46:00), recording with Garry Shandling (55:00), Aaron Rodgers’s UFO obsession (1:03:00), the power of boredom (1:12:00), and finding the weirdness with podcasts (1:20:00).