Shortly after taking over the NBC late-night spot formerly occupied by David Letterman, Conan O’Brien found himself on the precipice. Early critical reaction to Late Night With Conan O’Brien was lukewarm, and the ratings weren’t much better. “It was very raw. I was very inexperienced,” Conan remembered this week on the Conan O’Brien Needs A Friend podcast. “It was choppy waters for quite a while, and people thought maybe this isn’t going to work out.”
So it was big news when Letterman invited Conan to guest on his new CBS show. “It was the big number one show at the time,” Conan explained. “This was a big deal to get to go on Dave’s show and promote the show that we were doing a couple of blocks away.”
But what kind of bit could Conan do on Letterman’s show? He brainstormed with his writers, throwing out funny stories that might make the audience laugh. Then, as a goof, O’Brien suggested a bit he often did in the writers’ room. “What if I just walked out there and David Letterman said, ‘All right, well this next gentleman took over our old show that’s on at 12:35 on NBC. Please welcome Conan O’Brien.’”
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Paul Shaffer and the band would play, Conan would shake Dave’s hand, and Letterman would ask some kind of innocuous question about how the show is going. Conan would begin to respond, “Well, Dave, I just got to tell you…” and then O’Brien’s face would glitch as if he were some kind of comedy android that just went on the fritz. Conan would stay stiff as a statue.
After trying in vain to unfreeze O’Brien, Letterman would have no choice but to cut to commercial. To ratchet up the discomfort, O’Brien wouldn’t tell Letterman or his producers about the bit beforehand. “I wasn’t serious,” Conan insisted, but his writers thought the gag was perfect for Letterman’s show. “Robert Smigel, who’s the headwriter at the time, said, ‘You have to do it. Not only should you do it, you have to do it.’”
O’Brien reminded his podcast crew that, at the time, his show was hanging on by a thread. In fact, it was briefly cancelled at one point before NBC realized it had no backup plan. A stunt like freezing on Letterman’s show could have been the final straw.
And yet, Smigel was insistent, comparing the bit to an Andy Kaufman gag. “America would in that moment realize Conan has broken the sound barrier of comedy!”
But O’Brien chickened out. “I was new and nervous,” he confessed, revealing that he told funny stories instead. After all, who knows how Letterman would have responded? There was a chance he would have loved the bit, but “I think he would have loathed it.”
O’Brien shuddered at the thought. In an alternative universe, he said, a Letterman show exists where he froze like this:
“That Conan,” said co-host Sona Movsesian, “is working in accounting.”
Content shared from www.cracked.com.