If there was a competition for WTF guest who comes from the most far-flung, middle-of-nowhere place, comedian Ian Bagg would probably win by a lot. Ian tells Marc about growing up in Northern British Columbia, being part of the blast crew in a gold mine, and realizing that the satisfaction he got blowing things up was equaled only by doing stand-up comedy. Also, Bert Kreischer returns to the show on the cusp of a mid-life crisis that is mitigated a bit by his new Netflix special. This episode is sponsored by the Around The NFL Podcast, NHTSA.gov, SimpliSafe, and ExpressVPN.

Jo Koy is one of the biggest headlining comedians in the world and it might not have turned out that way if he hadn't become a vigorous self-promoter. Jo tells Marc how moving around a lot as part of a military family and dealing with his brother's severe mental illness  made him realize that if he was going to do something big, he had to do it himself. Jo and Marc also talk about holding down other jobs while doing comedy, the hazards of burning through material, and why people mistakenly think being a stand-up is easy. This episode is sponsored by The Jim Jefferies Show Podcast, ZipRecruiter, and Starbucks Doubleshot.

Jay Leno came up as a comic's comic, a performer recognized by other comedians as one of the best in the game. He also became one of the most successful late night television hosts in history, not once but twice. Those two sides always seemed at odds with each other, especially in the minds of many other comics, but Jay never saw it that way. He tells Marc about the early days in the clubs with Pryor, Carlin, Robin and others, how he and Letterman influenced each other as comics, and how things went south as they both made it big. And then there's the whole Conan thing. Marc and Jay deal with all of it, and then some. This episode is sponsored by The Happytime Murders, Sennheiser CX Sport Headphones, ZipRecruiter, and Stamps.com.