Comedians Jay Larson and Sean Patton drink their way down the southern California coast, where they find an old stagecoach stop in the mountains of Santa Barbara, a pop-up culinary cocktail bar in a Venice garden, a beachfront dive with the coldest beer in SoCal, and comedian Bill Burr.

In Chicago, comedians Jay Larson and Sean Patton learn booze's mobster roots. They get the Picasso treatment at a neighborhood landmark, take in the comedy scene with Pete Holmes, and get a taste of the local music with Blues legend Buddy Guy.