23. Yambo (The Late Late Show with Craig Kilborn)
When it debuted: 2000
Segment lowlight: Deciding between Vern "Mini-Me" Troyer vs. Patricia Heaton and Dave Grohl vs. Jason "Jay" Mewes would imply that one is not the most terrible thing ever, and we're not willing to cut either slack.
Kilborn has had a dream career by anyone's standards. His résumé reads like a list of "best hosting gigs of all time," as he is a veteran of The Late Late Show, The Daily Show, and SportsCenter. All of the shows seem to hit their stride right after he leaves. Coincidence?
Kilborn tried several tricks to spice up the celebrity interview format while he was a late-night host. One of them, dubbed "Yambo," involved Kilborn circling two celebs and shouting relatively simple questions at them. The first guest to answer three correct won. Just about as funny as it sounds.
In 2010, Kilborn attempted a return to late night with The Kilborn File. During the show's run, he tried to bring back Yambo, renamed "Kilbo." Shockingly, the show was cancelled after just six weeks.