Even for the most die-hard fans of Stephen Colbert, it’s hard to predict what a Colbert-manned “Late Show” will look like. His blowhard right-wing persona, needless to say, could hardly be more different from Letterman. Out-of-character Colbert appearances have been scarce. But Letterman and Colbert do have some things in common: like Michelle Obama, Bill O’Reilly and Bill Clinton, to name a few of the bigwigs they’ve both had in the hot seat. For clues into the future of “The Late Show,” we did a side-by-side comparison of the current and future hosts. The verdict: a Colbert-Letterman mashup might be the best “Late Show” host of all.
Michelle Obama, 2012
Letterman to Michelle Obama: “Does your husband ever come home to you and say to you, ‘Hey, did you see what Todd Aiken said?'”
Colbert to Michelle Obama: “I hope I’m not out of place in saying this: You’re a very good looking lady … Do you think your husband will be okay with me having said that?”
Bill O’Reilly, 2006
Letterman to O’Reilly (asked if he wants America to win in Iraq): “That’s not easy for me, because I’m thoughtful.”
Colbert to O’Reilly: “I don’t retain anything in books, okay, they’re just squiggly lines … I believe that books are, well, full of facts, okay. I’m more of an opinion man.”
Drew Barrymore, 2012 and 1995
Letterman to Drew Barrymore: “What was your relationship like with Steven Spielberg, who is now like, Mr. Bigshot, the biggest most powerful in the world?”
Colbert to Drew Barrymore: “Can we talk about ‘E.T.’ for a second? You cry in that movie. Did Spielberg make you cry? Cause if he harmed a hair on your head … I will protect you. He is a jerk.”
Bill Clinton, 2013
Letterman to Clinton: “You and I have something in common, which is we’ve both had the heart surgery.”
Colbert to Clinton: “Sir, I took the liberty of opening you a Twitter account. Now ‘PresidentClinton’ was taken, WilliamJeffersonClinton’ was taken, but ‘PrezBillyJeff’ was available.”
