4. Conan Records a Song in Memphis (1994)
It really can’t be said enough just how different Late Night with Conan O’Brien was compared to other late night shows of the mid-1990s. It may have been slow moving at first but the momentum of the show was always driven by Conan’s dedication to every bit.
We’ve seen it before on this list but it is hard to picture anyone else in late night wearing a cowboy outfit and gyrating in a Memphis recording studio like we see Conan do. Similar to the Hilton Furniture commercial we have the “terribly misplaced self-confidence” Conan. Again using his relative unknown status of the early years, Conan is willing to let himself be dismissed and put down by strangers without fighting back.
Music has always been an important part of Conan O’Brien’s shows and his comedy. Fans have seen him play guitar onstage and in behind-the-scenes clips. The recording of “Late Night Cowboy” shows that even in the earliest days of Late Night with Conan O’Brien, the host was trying to incorporate his own talents and passions into the show. It supported the lofty goal Conan set, and achieved, of making himself and his sensibilities the center of a successful comedy program.