In some ways, you have to feel for late-night host Conan O'Brien simply because of the two major events that affected his comedy legacy with his final show last week on TBS. While he's not going away as a personality, he's simply adopted a similar route as his Late Night predecessor David Letterman taking his talents to streaming. In this case to HBO Max hosting a weekly variety series. While O'Brien's used his comedy to entertain his audiences for the greater part of 28 years, it's hard to avoid talking about his career without his 2010 Tonight Show debacle and how his series on TBS barely returned as Hollywood starts getting back to normal from the pandemic.
NBC's Tonight Show Disaster from Leno to Conan
With writing stints on The Simpsons and Saturday Night Live, O'Brien achieved his dream as a talk show host replacing the aforementioned Letterman for NBC's Late Night when his contract expired. Letterman's decision to leave NBC stemmed from the network's refusal to grant him The Tonight Show following Johnny Carson's retirement in 1992 in favor of comedian Jay Leno. With Letterman's decision to leave for CBS to create The Late Show, the two battled over late-night supremacy with Leno getting the better of the two for the bulk of it in the ratings. NBC's clauses in Leno and O'Brien's contracts allowed them to make one of their most boneheaded decisions of network television. Leno would leave the Tonight Show in favor of a 10 p.m. slot and hour-long format called The Jay Leno Show that would lead into local news before the Conan-hosted Tonight Show in 2009. Unfortunately, ratings from Leno's Tonight Show audience didn't translate to his new time slot and O'Brien wasn't delivering enough in ratings for NBC regularly losing to Letterman's Late Show. As a meek attempt at a compromise, NBC offered Leno his old 11:30 slot and bumped Conan to midnight. Naturally, Conan scoffed at the notion which led to NBC buying out his contract and moving Leno back to hosting The Tonight Show in 2010.
During the debacle, NBC went through a wringer of sorts not only from the shade cast by O'Brien himself during his stint as Tonight Show host but also from Letterman and ABC's Jimmy Kimmel also joined in on not only attacking the network and Leno. For his part, Leno actually allowed Kimmel to roast him in a Tonight Show segment and he also recorded a series of Super Bowl ads on CBS to promote The Late Show along with Oprah Winfrey and Letterman. It wouldn't be until three years later when Jimmy Fallon, who was the successor to O'Brien on Late Night, took over The Tonight Show permanently.
Once O'Brien's exit clause of his TV contract expired on NBC and his comedy tour completed, he made his debut on his own self-titled program Conan on TBS in November 2010, which coincidentally followed up another talk show initially hosted by George Lopez. Despite offers from Fox, Conan went to cable instead and outside of network TV. With Letterman's retirement from the Late Show in 2015 and Stephen Colbert taking over and Fallon taking over for Leno (for good) in 2013, the field in 2021 is dramatically different in the streaming era with so many options including other talk shows emerging via streaming platforms with talents like Chelsea Handler, Larry Wilmore, and Amber Ruffin.
Perhaps O'Brien saw the writing on the wall and the lack of sustainability in a format he couldn't really creativity compete anymore. As one of the last remaining relics of the late-night era in the 1990s, he served up the laughs along with Andy Richter for the bulk of his runs, but they hit a brick wall in an oversaturating market. Personally, I'll always have a deeper appreciation for Conan, his self-deprecating humor, and segments like Butterscotch the Clown, Triumph the Insult Comic Dog, the Masturbating Bear, and many more. Far be it for me to dredge up old skeletons in celebration of a comic genius, but I'll have Kimmel here sum up how people will "remember" Conan in "congratulating" Leno on his new hosting gig.
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