The guys head to Sean's hometown of Chicago with special guests Andy Richter, Jeff Tweedy and Mark Cuban.
1. Tuxedos and Cool Sunglasses
Aired: May 23, 2023Will, Jason, and Sean kick off the tour in Washington, DC, and nervously prep...
Aired: May 23, 2023 The boys brave an ice storm in Boston with special guests Conan O'Brien and M...
3. Sorry, Did I Lean on Your Laugh?
Aired: May 23, 2023The guys hit the Big Apple with guests David Letterman and Alexandria Ocasio-...
Aired: May 23, 2023 The guys head to Sean's hometown of Chicago with special guests Andy Richter,...
Aired: May 23, 2023 A very special Madison show with Matt Damon and a visit from Sean's sister (a...
Aired: May 23, 2023 The guys finish out their tour in Los Angeles with special guests Kevin Hart ...
Streaming in:
Guest Staring
Appearances
Currently you are able to watch "SmartLess: On the Road" streaming on Max.
