Conan O'Brien and Kristen Wiig trade SNL bomb stories

World Premiere of Apple TV+'s "Palm Royale"
World Premiere of Apple TV+'s "Palm Royale" / Eric Charbonneau/GettyImages

It's hard to think of two people with more success in late-night TV than Conan O'Brien and Kristen Wiig. But for a pair of comedians who always seem on, there have been times when they completely bombed.

Wiig stopped by the March 25 episode of Conan O'Brien Needs a Friend to promote her new Apple TV+ series Palm Royale. The conversation started with Saturday Night Live, where O'Brien and Wiig traded stories about some famous bombs.

For Wiig, what stood out was how poorly a sketch transitioned from the writers' room to dress rehearsal. She recalled a sketch that got the best reaction she'd ever received while at Saturday Night Live. According to Wiig, the sketch she co-wrote with Jillian Bell left earned applause from the writers' room.

Things immediately went south when the sketch went to dress. Wiig admitted that the first joke didn't land, setting up the sketch for failure. The Saturday Night Live star revealed the silence was something completely unexpected, even if she kind of liked it.

"I couldn't even predict that that was going to happen," she told O'Brien. "But it's good also because it kind of keeps you on your toes. But the way that it bombed was for the books."

Not to be outdone, Conan O'Brien shared his own SNL failure story. His involved a sketch he wrote for the legendary Phil Hartman.

Hartman played Mace, an over-the-top tough guy in prison. But his macho persona dropped when it came time to use the toilet in front of his cellmate. O'Brien described how Hartman would become very timid and nervous about going to the bathroom while another man stood nearby.

"We did it at readthrough," O'Brien said, "and like tile was coming off the ceiling people were laughing so hard. And it's over, and the applause, and people coming up, and Lorne [Michaels] actually making eye contact."

But similar to Wiig, O'Brien found out that the sketch didn't exactly translate outside of the SNL offices. The dress rehearsal version bombed as the audience failed to connect with Mace or laugh at any part of the premise.

To add to O'Brien's embarrassment, he had called people ahead of time to let them know he had an instant classic sketch on that week's show. The reality was that the sketch was dead on arrival and never made it to air.

O'Brien and Wiig couldn't come up with an explanation for why certain sketches don't work once it's time to act it out. For O'Brien, it really comes down to "magic" and the right material hitting the right audience at the right time.

If that's the case, then he and Kristen Wiig have found that magic much more often than they've bombed. But it's also a nice reminder of how often failure is part of comedy no matter who's behind it.