Watch Conan O’Brien Fall in Love With His Future Wife During This 2000 ‘Late Night’ Sketch

Chainsaws are better known for tearing things apart rather than bringing them together, but the ballad of Conan and Liza couldn’t have been written without a ripper. 

Back in 2000, many regional NBC affiliates had an interesting policy of allowing a local madman to plan their nightly schedule. Due to this unorthodox programming philosophy, there was a two-and-a-half hour break between the end of The Tonight Show with Jay Leno and Late Night with Conan O'Brien in the Houston market, pushing the latter late-night show all the way back to 2:10 a.m., a time slot that attracts the most unusual of local sponsors. 

In order to playfully call out Houston’s scheduling lunatic for his shoddy work, Conan O'Brien decided to select one such Houston sponsor for an “advertising makeover,” in which he would enlist the help of a top New York ad agency to punch up the early morning commercials that punctuated the show’s Houston airings.

In the sketch, Conan met with a group of copywriters from Foote, Cone & Belding, a committee that included one Liza Powel. And, as O’Brien and Powel came together to give Hilton’s Furniture and its chainsaw-wielding owner a commercial facelift, sparks flew between the late-night host and his soon-to-be lady love.

Along with foreshadowing O’Brien’s future family, this sketch also includes what must be the most hilariously ironic line in late-night history of, “When Jay Leno tells you something, that’s supposed to be a pact with the American people.”

While O’Brien strains to stay in character despite sitting across from his soulmate, you can clearly see Powel’s face light up whenever he cracks some joke about voting for John McCain or Michael Jordan’s Gatorade sweat. The cameraperson even seems to pick up on the chemistry between the future husband and wife around the 7:30 mark when he lingers on a close-up of Powel’s smiling face before panning to O’Brien who leers into the lens as if to say, “Don’t you dare blow this for me.”

Both O’Brien and Powel have discussed this sketch at length on various late-night shows and podcasts in the near-quarter century since their chance, chainsaw-centric meet cute, during which they’ve raised a family of four. O’Brien’s long-time writer and collaborator Mike Sweeney once confirmed that the crew knew their boss had a huge crush, especially when he invited the advertising team out for dinner after they finished the segment even though he still had a show to shoot that night. O’Brien has also mentioned that Mr. Hilton of Hilton’s Furniture attended their wedding in 2002, having been the chainsaw-wielding, chaise-lounge selling catalyst for their relationship. 

But the legend of the sketch above is best described by O’Brien during the final episode of, well, Conan, when he commented of the scene, “You can see me fall in love with her on camera,” calling Powel, “The best decision I’ve ever made in my life, including Late Night.” And, though Conan fans continue to return to this sketch after so many years, O’Brien says that he’s never once rewatched the segment, choosing instead to keep the memory of his first meeting with the woman of his dreams pure in his mind.

If that doesn’t make you want to fall in love, then it should at least make you want to buy a loveseat.