1. Conan O’Brien, The Tonight Show

1. Conan O’Brien, The Tonight Show

Most of the hosts on this list failed on their own merits, but Conan O’Brien had lots of help. It’s still open to debate whether the absurdism that made O’Brien a beloved figure on Late Night could have translated to a major network’s 11:35 time slot. But America never really got a chance to find out. After building its new host a multi-million-dollar studio and hyping up his ascension to the late night throne, NBC cut O’Brien off at the knees, canceling or rescheduling all of the network’s 10 p.m. (Eastern) weeknight shows and turning those hours over to O’Brien’s predecessor, Jay Leno.



What resulted was a legendary debacle, as Leno siphoned his loyal viewers away from O’Brien, and both shows suffered (as did the network, which found that a nearly uninterrupted four-hour block of talk shows wasn’t as appealing to viewers as ER had been). Only seven months into O’Brien’s tenure, NBC somehow made the situation worse by floating a novel idea: Move Leno’s new show into The Tonight Show’s time slot and push Tonight, Late Night, and Later back half an hour. O’Brien refused to play along, insisting he didn’t want to see one of TV’s most venerable institutions diminished further. NBC ended up buying out O’Brien, putting Leno back behind his old desk, and everything was as it was before. Except that the network was out $45 million, had no 10 p.m. shows, was stuck in last place, turned much of America against Leno, spawned other late-night competitors (as O’Brien rebounded with Conan on TBS), and cemented its reputation for network incompetence. [Mike Vago]