Politicians, rock gods, movie icons, and cult legends — fifteen years of late-night television's most talked-about interviews. Who delivered the greatest moment?
1Jon StewartColbert's Daily Show mentor whose Late Show appearances sparked some of the sharpest, funniest conversations in late-night history, with a final-week appearance cementing their friendship.
2Bruce SpringsteenThe Boss delivered soul-stirring performances and candid conversations across multiple Late Show visits, including a celebrated final-week send-off performance.
3Tom HanksAmerica's favorite everyman who appeared multiple times with natural warmth and storytelling charm that made every visit feel like a must-watch television moment.
4David LettermanThe original Late Show host who returned to his old desk to trade barbs with his successor in one of late night's most surreal and heartfelt reunion moments.
5Conan O'BrienColbert's late-night rival who flipped the script during a memorable appearance, switching seats with his host and turning a standard interview into a comedic highlight reel.
6Tina FeyThe Saturday Night Live alum and 30 Rock creator who matched Colbert wit for wit in recurring appearances that rank among the most electrifyingly funny exchanges the show produced.
7Meryl StreepThe most nominated actress in Oscar history who brought grace, humor, and unexpected candor to her Late Show visits, always leaving the audience wanting more.
8Oprah WinfreyThe media titan whose Late Show appearance in the final stretch of the show's run created one of the most watched and emotionally resonant moments of the entire series.
9Julia Louis-DreyfusThe Seinfeld and Veep star who delivered consistently hilarious and surprisingly vulnerable interviews over more than a decade of Late Show appearances.
10Lin-Manuel MirandaThe Hamilton creator and polymath entertainer who brought boundless enthusiasm, surprise musical moments, and genuine intellectual depth to every Late Show visit.
11David ByrneThe Talking Heads frontman who delivered one of the Late Show's most unforgettable musical moments in the final week, as performer and as a deeply thoughtful interview subject.
12Stephen KingThe master of horror who revealed himself to be warm, self-deprecating, and brilliantly funny in a series of Late Show conversations that doubled as must-read author interviews.
13Emma StoneThe Oscar-winning actress whose Late Show visits showcased a gift for self-deprecating humor and charming awkwardness that made her one of the most magnetic guests on the couch.
14Barack ObamaThe 44th U.S. President turned cultural icon whose Late Show appearances — from résumé gags to candid reflections on legacy — ranked among the most-watched in the show's history.
Comments 1
On May 14, 2026, Letterman sat on Colbert's couch, a week before the Late Show he founded went dark: https://youpick.best/articles/david-letterman-ranked-many-ways
YP
ypb-team7 days ago



















