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For Tracey in Wisconsin
SmartLess: On the Road - S1 - E5
A very special Madison show with Matt Damon and a visit from Sean's sister (and fan-favorite), Tracey.
SmartLess: On the Road: Season 1 - 6 Episode s
1x1 - Tuxedos and Cool Sunglasses
May 23, 2023
Will, Jason, and Sean kick off the tour in Washington, DC, and nervously prep for their first live show ever with special guest Will Ferrell.
1x2 - Sashimi!
May 23, 2023
The boys brave an ice storm in Boston with special guests Conan O'Brien and MIT physicist Max Tegmark.
1x3 - Sorry, Did I Lean on Your Laugh?
May 23, 2023
The guys hit the Big Apple with guests David Letterman and Alexandria Ocasio-Cortez, plus an extra-special cameo.
1x4 - Portillo's for the Burp
May 23, 2023
The guys head to Sean's hometown of Chicago with special guests Andy Richter, Jeff Tweedy and Mark Cuban.
1x5 - For Tracey in Wisconsin
May 23, 2023
A very special Madison show with Matt Damon and a visit from Sean's sister (and fan-favorite), Tracey.
1x6 - Time Flies Byeeee
May 23, 2023
The guys finish out their tour in Los Angeles with special guests Kevin Hart and Jimmy Kimmel.