Jay is joined by his good friends Chet Siegel (Uncle Peckerhead, Alternatino) and Ellen Haun (How to Get Away with Murder) to play a wild game of 500. There's the Country Bumpkin Round, FMK about Prince Charles, Charlie and the Chocolate Factory and Charles de Gaulle, and a Ones Gotta Go about Sex Love and Breakfast. Just saying.…

Jay is joined by his friends, hosts of the podcast INSERT MOVIE HERE: The Musical, Sam French and Kyle Wilson, to talk about musicals, Claudia Conway, Seal, and play a very good game of 500!由Jay Wolff

Jay is joined by his dear friends Jess Smetana and Priya Desai to play 500!, talk about sports and non-sports, and make some big decisions about which Chrises Gotta Go.由Jay Wolff

Season 2 is here and with it, Jay's friends Kira Kosarin and Audrey Whitby. They play 500, discuss how to make Jay popular with the youths, and much, much more. Music credit: Quiet Night by Tokyo Music Walker | https://soundcloud.com/user-356546060由Jay Wolff

Jay is joined by his very good friends, hosts of SportsCenter on Snapchat and Chiney and Golic Jr., and all around great human beings, Gary Striewski and Mike Golic Jr. for a real good round of 500! The game includes The Dude Bro Round, the debut of the One on One round, and a big plot twist.由Jay Wolff

Jay is joined by comedians, friends and internet sensations Ester Steinberg and Eric Williams to compete in a surprisingly NSFW game of 500. Tune in for the Shoes round, the return of the Name That Song round, and some big closing arguments about quantum physics and formalwear.由Jay Wolff

Jay is joined by his friends, comedians Di Billick and Sam Beaver, who are married (!) to compete in a raucous game of 500. Featured rounds include The Tony Hawk Pro Skater Round and The Haiku Round. You're gonna wanna get it in your ears.由Jay Wolff

Jay is joined by comedy writer Eden Dranger (The Unicorn) and musician Ben Lee to play a very good game of 500!由Jay Wolff

Jay is joined by his friends, comedians Atsuko Okatsuka and Clayton Farris, who between the three of them host 5 different podcasts. It's a rollicking good time.由Jay Wolff

Jay is joined by comedians Steve Hofstetter and Dan Muggleton, hosts of "Ask Us Anything," for a very rousing game of 500.由Jay Wolff

Jay is joined by friends Ellen Haun (How To Get Away With Murder) and Joel Marsh (#BlackAF, Chef's Table) to compete in the very first game of 500.由Jay Wolff