- Kimmel for Mayor of Dildo
- Roselyn Sánchez on Grand Hotel & Sexy Billboard in Times Square
- 14th Annual Summer Belly Flop Competition
- Whitney Cummings on Her Sex Robot, Meeting Celebrities & Her New Fiancé
- Bob Odenkirk on Better Call Saul & Son Working at Kimmel
- Guillermo's First Dildo Experience
- Massachusetts Has the Best Drivers???
- Leslie Jones on Angry Birds Addiction & Stand Up Special
- The Miz Is Not a Villain Anymore
- Ben Stiller on Meeting Obsessed Fan on Subway & Escape at Dannemora
- Robin Thede on Denzel Washington & A Black Lady Sketch Show
Guillermo's First Dildo Experience
Aug 13 2019
Over the last couple of weeks, Jimmy's future has become more clear with his new plan to move to Newfoundland, Canada to become Mayor of the small but fascinating town of Dildo. We sent Guillermo to Dildo, to lead the advance team for Jimmy's mayoral run. With the help of the local Dildodians, the team has been distributing signs for supporters all over town. Jimmy checks in with Guillermo at his campaign headquarters at the Dildo Cove Coffee and Krafts with our new pals.
