Let’s Look Back At Stephen Colbert’s Best Interviews From ‘The Colbert Report’

When David Letterman signs off for the final time as the host of The Late Show, it will obviously be the end of a great era, but also the beginning of what we hope will be a new one with Stephen Colbert replacing him. The thing is, we’ve got a long empty valley between those two points because Colbert won’t take the reigns until September 8. In the meantime, we can look back on some his best interviews from The Colbert Report.

When he called Laura Ingraham a terrible writer.

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If you don’t know, Laura Ingraham is a conservative commentator who often appears on Fox News. In 2010, she appeared on The Colbert Report to promote her book The Obama Diaries, a fictionalized “diary” by the Obama family (with a few entries from Joe Biden), which, as Colbert points out, just happens to match up perfectly with the conservative narrative about the president. Colbert brilliantly slams Ingraham when he notes that Obama must be dumb because “this writing is terrible!” For the rest of the interview, Ingraham is visibly flustered, which I would be, too, if someone called me a terrible writer to my face. All I have to deal with is the comment section!

When Robert Wexler gave us the most memorable “Better Know a District” ever.

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In 2006, Florida Congressman Robert Wexler was running unopposed for re-election, and when he was interviewed for Colbert’s “Better Know a District” segment, Colbert decided to have a little fun with him. The idea was to get Wexler to say things that would really cost him the election, being that he as running unopposed. This included the now-famous phrase, “I enjoy cocaine because it’s a fun thing to do.” The interview caused a bit of controversy at the time (even though it was clearly a joke), and was likely a big part of why Rahm Emanuel advised congressmen not to go on The Colbert Report.

When he and Jane Fonda got a bit flirty.

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It takes a lot to get Stephen Colbert to break character, but Jane Fonda managed to pull it off in this 2007 interview. The two already had a flirty history together after the “Cooking With Feminists” segment from 2006, which featured Fonda and Gloria Steinem. Here, though, things turn into a full-fledged make out session, with Fonda complimenting Colbert on his luscious lips. Hey, just because he’s a high-status idiot doesn’t mean he can’t be a charmer.

His J.R.R. Tolkien trivia contests with James Franco.

Another way to get Colbert to break character? Challenge him on his knowledge of J.R.R. Tolkien. As James Franco learned on two separate occasions, Colbert is nothing to mess with when it comes to Tolkien trivia. His immense Tolkien fandom is why it wasn’t too shocking when he had a certain unexpected guest during his final week…

When he interviewed Smaug.

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One of Colbert’s last few interviews was also his best, as Smaug appeared as himself to promote The Hobbit: The Battle of the Five Armies. While the surreal site of Colbert interviewing a CGI creature alone is worth the price of admission, the true greatness here is hearing Benedict Cumberbatch call himself a hack while in character as Smaug. Leave it to Colbert to get another confession out of another famous guest.