The Daily Show host challenged his Monday night guest to switch places: Collins played Trump, Stewart played Collins—and asked the question he wishes she would.
Jon Stewart Puts Kaitlan Collins Through a Trump Role-Play
27 minutes ago
More Videos
Fallon’s Tonight Show Debuts Its Own Microdrama, Beating The Daily Show to the Punch
2 hours ago
2 comments
Kimmel Guest Host Rosie O’Donnell Says She’ll Keep Trump Hits Coming
Jul 24, 2026
16 comments
SNL and The Daily Show’s Lookalike Pitt Spoofs Earn Rival Emmy Nods
Jul 22, 2026
1 comment
Before They Were SNLers: Chloe Fineman on Jane the Virgin
Jul 20, 2026
1 comment
The Daily Show Shares Unaired Video of Desi Lydic Bit Going Off the Rails
Jul 17, 2026
1 comment
LateNighter Podcasts
