This week, Defector has turned itself over to a guest editor. Brandy Jensen, former editor at Gawker (RIP) and The Outline (RIP), and writer of the Ask A Fuck Up advice column (subscribe here!), has curated a selection of posts around the theme of Irrational Attachments. Enjoy!
There is a clip that I love to revisit. It’s from Late Night with Conan O’Brien, the legendary '90s/2000s talk show that put O'Brien on the map, and it involves a Howard Stern visit from 2006. For context, Conan had recently announced that he would be taking over The Tonight Show from Jay Leno in 2009, a strange and arbitrarily timed decision that would only lead to problems. Stern was happy for Conan but remained unconvinced. “Do you really think that’s gonna happen?” he asked, to which Conan gave a typically self-deprecating answer. “I don’t see this guy leaving and I’m concerned for you,” warned Stern.
Stern’s caution and subsequent ridiculing of Leno was a warning to the eternally optimistic Late Night host about Leno’s history of doing anything short of murder to get and hold onto The Tonight Show. Whenever I revisit the clip, I invariably move on to clips from a few years down the road, from when Conan, having only recently taken over The Tonight Show, knew he had already lost it. I'll watch a clip of Conan “burning through” NBC’s money because he’s getting fired, so who cares! There's a clip of a classic Norm Macdonald visit where the comedian gives his own kind of thoughtful send-off. I also enjoy the clip of Steve Carell giving Conan his exit interview. Despite a few stinging jokes at NBC’s expense, Conan’s last weeks of television were a celebration, for fans like me who watched it all go down in real time, and for late-night television as a medium.
There was plenty of palace intrigue around O'Brien and Leno's battle over The Tonight Show, but the most important thing to remember is that Leno loved being known as the host of The Tonight Show more than actually hosting it. But in the early aughts, O'Brien was the hottest thing in television. He was also up for a new contract and was being heavily courted by ABC and FOX. O'Brien wanted to stay at NBC but for a price: a shot at hosting The Tonight Show. The network loved Leno, but they also wanted to keep O'Brien and, more importantly, not let him go to a competitor. So they settled on a five-year succession plan, thinking maybe Leno will be ready to move on by then. After all, five years always seems so far away in the moment.
Five years passed and Leno wasn't ready to go. So, to keep Leno happy and, more importantly, not let him go to a competitor, NBC invented a new 10 p.m. show for him. That disaster of a show didn't last a year, but NBC still wanted its cash cow back in control and kept doing things that even a bunch of network execs, whom I have no respect or admiration for, had to realize was stupid. Chief among them: a proposal to move a new Jay Leno show to 11:35 p.m. and Conan’s Tonight Show to 12:05 a.m. O'Brien rightfully pointed out that The Tonight Show ceases being the TONIGHT Show at 12:05 a.m., but by this point he could see the writing on the wall. The network had to choose between O'Brien and Leno, and they ultimately went back to Leno.
So why do I, an avowed Conan fan, keep revisiting clips from arguably the worst period in his career? I wonder myself sometimes. I think part of it is the effect it had on the entire late-night ecosystem. Like any other fan of late-night television, I love David Letterman. He is the architect of a certain brand of left-brained comedy that fostered a guy like O'Brien, and in 1993 he went through a very similar battle with Leno, as immortalized in the made-for-HBO movie The Late Shift. Despite the fact that Johnny Carson himself would’ve loved Letterman to be his successor, Jay Leno hid in a closet, listening in on NBC execs as they deliberated the future of the show, in an effort to situate himself to get that job. He fired his high-powered agents to get that job. He would’ve done whatever was necessary to get that job. He is the company’s man. When Letterman lost out on the job, it was disappointing and disheartening, until CBS came calling and offered him gobs of cash to start their new late-night rival to The Tonight Show. For a while, he was beating Leno in the ratings, too, until eventually settling into second place. The Dave of 2009 can sometimes feel worlds away from the Dave of 1993; he didn’t have quite the same hunger or interest by the later years of The Late Show, but then an old nemesis got back to his tricks and suddenly Letterman seemed rejuvenated.
Look at him! He is absolutely giddy. He had a blast getting to dig at Leno and NBC for old times sake, peaking with his “don’t blame Conan” segment. It is no wonder that the minute O'Brien could go back on television after the whole debacle, he chose to go see Letterman. Another guy who really enjoyed all of this? Jimmy Kimmel. He was still pretty new to late night on ABC, but like O'Brien was an acolyte of Letterman, and was happy to start his own feud with Leno on his show. Kimmel even did an entire episode dressed as Leno, which got the attention of Leno, who then brought Kimmel onto his 10 p.m. show while it was still on. It was a very big mistake.
There’s something heartening about the way late night rallied behind O'Brien, a testament to how beloved he was but also how respected he was. From Saturday Night Live to comedians on radio shows, they all had something to say about it; they all tended to be more empathetic toward O'Brien. But more than that, I think the reason I keep revisiting this moment in time is because it truly signaled the end of something I really loved.
Late-night television was a big deal before Twitter. I remember trying to stay up just to watch the shows with my dad. It was a badge of honor to make it up past my bedtime and watch something “adult.” I didn’t get half the jokes, but I didn’t care about that part. I loved late-night talk shows so much that I loved The Larry Sanders Show, despite not being anywhere near old enough to get it. The first time I stayed up late enough to catch Late Night with Conan O’Brien, it was like an instant rewiring of the brain. I adored that show and the gangly redhead at the helm of it. He had a mind a grownup could appreciate and the sort of physical presence and zaniness that naturally appeals to a child.
Late night was already losing steam by the time Conan’s Tonight Show started, not because of anything the writers were doing, but because people were starting to spend more time on the computer, and then their phones. Television would only become more fragmented and the next generation of talk-show hosts (Jimmy Fallon, Seth Meyers, Jimmy Kimmel, Desus & Mero) would increasingly cater to a niche audience. In many ways, this was late night’s last gasp. Leno got his show back, for a little bit, and then was pushed out again for Jimmy Fallon, this time with no chance to hide in another closet. O'Brien was famously paid off to go away and was barred from television for nearly a year, perhaps in the hopes that he wouldn’t be able to capitalize off all the goodwill. Instead he went on tour and then to basic cable, seemingly a demotion. But to O’Brien’s credit, he saw the landscape changing and found a way to survive. He recently did an appearance on Hot Ones that went viral and caused an outpouring of fond remembrances of Conan’s contributions to television over the last 30 years. As it so happens, the guy that NBC didn’t think could return The Tonight Show to dominance has become the last showman in Hollywood, beloved by nearly everyone. And what better revenge in the end than that?
