Weird Al Yankovic joins Samantha Bee to discuss their unique meet-cute, and how their interview came to be due to a scam gone right. Al tells Sam about how he’s actually happy with all the choices he’s made in life except (other than wishing he had bought Apple stock) and yet he agonizes over little decisions—especially when editing music videos. He reveals that the ultimate dig at him is when people say he’s talented enough to do “real music”, why record companies beg for Christmas albums, and turning down an opportunity to open for Duran Duran at Madison Square Garden.

Keep up with Samantha Bee @realsambee on Instagram and X. And stay up to date with us @LemonadaMedia on X, Facebook, and Instagram.

For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

See omnystudio.com/listener for privacy information.