Smartless: On The Road

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.

The boys brave an ice storm in Boston with special guests Conan O'Brien and MIT physicist Max Tegmark.

The guys hit the Big Apple with guests David Letterman and Alexandria Ocasio-Cortez, plus an extra-special cameo.

The guys head to Sean's hometown of Chicago with special guests Andy Richter, Jeff Tweedy and Mark Cuban.

A very special Madison show with Matt Damon and a visit from Sean's sister (and fan-favorite), Tracey.

The guys finish out their tour in Los Angeles with special guests Kevin Hart and Jimmy Kimmel.