The Most Awkward "Daily Show" Interview In History

Watch Craig Kilborn interview Jon Stewart before he took over The Daily Show. Be warned: it’s intense.

In an oddly prescient interview, a bearded Jon Stewart has a pointed conversation with Craig Kilborn on The Daily Show. Stewart would take over as the show’s host about a year or two later (the date of the original interview is unclear), much to media gossip columnists’ delight.

2. “This is a daily show commenting about the world, am I right?”


The most interesting moment of the video is around 2:45, where Stewart asks in response to Kilborn’s quip about his desire to talk about the JFK assassination, “I don’t know, I thought this was a political show, I’ll talk about whatever you want. This is a daily show commenting about the world, am I right?”

Pay close attention:

Kilborn: “So what do you think of the show so far?”
Stewart: “The show so far?”
Kilborn: “Not the interview, no, don’t judge it on this, but the show so far.”
Stewart: “Can I tell you something? Not to quote Michael Medved, but to me it’s a laugh riot.”
Kilborn: “That’s usually Lizz Winstead.”
Stewart: “I think you, my friend, are the glue that holds this thing together.”

Kilborn apparently gave Stewart a phone book to sit on in order to bring the two up to a similar height, which may help explain the motorized platform he employed in his recent debate with Bill O’Reilly, the Rumble in the Air Conditioned Auditorium.

Stewart’s annoyance is most palpable during the 5 Questions segment, responding to a question about the three “Happy Days” spinoffs with “Joanie Loves Chachi,” “Potsie Takes it in the Ass,” and “ER”.

The two finish with a final bit of hilarious forshadowing:

Kilborn: “That was fun.”
Stewart: “That was fun, and it’s so nice to ruin my career here with you.”
Kilborn (shaking hands with Stewart): “Let’s go down together.”
Stewart: “Do you want to? I’m with you.”

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