Jay Leno is rooting for Conan O’Brien to do well hosting the Oscars this Sunday. “I think he’ll be great,” Leno, 74, told the New York Post. “He’s a very funny guy. He’s very creative. I’ll watch, sure. He’ll do good.”
Warm, supportive, friendly. Right? No. “I did get asked twice,” he added. “And I sat down with my staff and… we realised that when you see somebody on TV every night, it’s not special to see them hosting the Oscars. I think Conan will be good, because he’s not on every night like he used to be… I think he’ll do fine.”
Ouch. “Not on every night like he used to be.” “He’ll do fine.” It looks like one of Hollywood’s longest-running feuds still hasn’t died down.
Conan O’Brien is a natural host for the Oscars. His comedy is snarky but friendly, he’s unlikely to roast the stars but will avoid being sycophantic and he brings to the stage his own personal struggles at a time when Los Angeles is still struggling to get back on its feet after the fires that swept the city. O’Brien’s house barely survived the flames and is still uninhabitable. The presenter knows personal loss, though. Just before Christmas, both his parents died just a few days apart – father Thomas on Monday 9 and mother Ruth on Thursday 12.
But the fact that he’s on that stage at all seemed unlikely a few years ago. His unceremonious removal from one of the finest pieces of US late-night prime time the Tonight Show sent him spiralling and even though he ended up on cable channel TBS for a few years, it’s taken his HBO travel show and his star-studded podcast, Conan O’Brien Needs a Friend, to restore his voice. He’s arguably now one of the most beloved figures in the entertainment industry; which is especially amazing, considering how badly it’s treated him.
The Leno/O’Brien celebrity ding dong that threw him off track is a feud with so many layers of snark, rumour and bitchery that if it was about two 1940s Hollywood movie stars, HBO would have made a drama about it. Conan was riding a wave of good fortune that propelled the middle-class Harvard graduate into the heartland of US TV comedy. He began his career as a sketch writer, moved to the writing team at Saturday Night Live then wrote for The Simpsons where he was part of moving the cartoon from focusing on the family to its current more surreal stories. (The classic episode Marge vs. the Monorail is one of his.)
When the legendary Johnny Carson retired as host of NBC’s chat-based institution The Tonight Show, NBC replaced him with stand-up comedian and stand-in host Jay Leno. David Letterman was presenting NBC’s late-night chat show Late Night and fumed at failing to get the gig so decamped to CBS. A new host for Late Night had to be found and Michaels hired Conan.
Arch rivals Conan O’Brien and Jay Leno in 2003 – Getty
His tenure started slow. NBC interns had to sit in the audience to fill seats and NBC were looking to replace him. By 2001, he’d turned things around, pulling in a young audience which advertisers loved. Fox started courting and as part of his negotiations with NBC to stay put, he demanded Leno’s job when he left.
In 2004, NBC’s CEO Jeff Zucker told Leno he had four more years then O’Brien would take the chair. Leno later described his conversation with NBC as “You’re fired four years from right now.” But Zucker held on to Leno, offering him a half an hour slot just before O’Brien. Leno debuted with Jerry Seinfeld and Kanye West as guests, shortly after West had stormed the stage when Taylor Swift won an MTV Award.
O’Brien’s show, on the other hand, struggled. His first episode was barely a chat show, mostly skits and jokes with just Will Ferrell goofing around as an interviewee.
Ricky Gervais with Conan O’Brien in 2014 – Getty
Ratings fell and after nine months, NBC decided to move Leno back to 11:35 pm. To make this seem like they weren’t just putting Jay Leno back on the Tonight Show nine months after he retired, they suggested bumping Conan to 12:05 am. He refused, releasing a statement that began “People of Planet Earth”, going on to say; “I sincerely believe that delaying the Tonight Show into the next day to accommodate another comedy program will seriously damage what I consider to be the greatest franchise in the history of broadcasting.”
He secured a $32 million payoff and an agreement to avoid any media for six months. Convinced that Leno had gone behind his back, O’Brien’s paranoia leaked out on screen. During his final monologue he advised any kids watching that, “You can do anything you want in life – unless Jay Leno wants to do it, too.”
Fans and celebrities – including Tom Hanks, Seth Myers, Tina Fey, Ricky Gervais, Howard Stern, Ben Stiller, Ice-T and Jon Stewart – formed Team Coco and leant vocal support in interviews and online. “You almost want to take [Leno] aside and ask him, ‘Why do you want this so badly?’” comedian Patton Oswalt said. “Because you don’t do anything with it.”
Jerry Seinfeld, Chris Rock, Billy Crystal and Jack Black backed Leno, but they didn’t have the on-air muscle of rival talk show host Jimmy Kimmel. An SNL alumnus with his own late-night show on ABC, Kimmel delivered an entire show in March 2010 dressed as Jay Leno, announcing “Let it be known that I am taking over all the shows in late night…”
The following night, Leno interviewed Kimmel, presumably not having seen Kimmel’s ludicrously oversized chin, and asked who he’d most like to interview.
“You and Conan together,” Kimmel replied. Leno stared down awkwardly and moved on.
“What’s the best prank you ever pulled?”
“I told a guy that five years from now I give him my show and then when the five years came I gave it to him and took it back almost instantly,” Kimmel snarked.
“Good prank, good prank…” Leno tried to style it out, but his own audience were cheering just a bit too much. And on it went.
“Ever order anything off the TV?”
“Like NBC ordered your show off the TV, you mean?”
“How many lap dances did you have in Las Vegas?”
“Jay, my mother’s watching the show – no, wait a minute, the show’s cancelled, nobody’s watching it. I don’t like strippers because they have this phoney relationship with money similar to the way you and Conan were on the Tonight Show together passing the torch.”
“Is there anything you’d like to host?”
“This is a trick, right, where you get me to host the Tonight Show and take it back from me?”
Conan O’Brien, right, with Liam Neeson, Steven Spielberg and Bruce Springsteen in 2014 – Getty
It’s almost unbearable to watch, but not quite as intense as Conan O’Brien Can’t Stop. Filmed whilst O’Brien served his six months off-air, it follows his first ever live show, the Legally Prohibited from Being Funny on Television Tour, prompted by the outpouring of fan love his exit inspired, prompting protests outside NBC and public demonstrations with chants and banners. Even though the tour sells out fast, it’s a painfully confessional journey. He feels needy and anxious, constantly relieving his NBC defenestration and doubting himself just before walking on stage.
Two years later, Conan was starting to get over it. He had a talk show on cable station TBS and he felt optimistic. “There are moments of, ‘What the hell happened? Why did that person do that or say that?’” he told the Hollywood Reporter. “But there’s also a lot of, ‘OK, let’s file this under There’s A Lot I Can’t Control.’ It helps that almost everybody involved in the craziness has been relieved of their jobs.”
As for Leno, “The odds are we will both leave this Earth without speaking to each other, which is fine,” O’Brien said. “There’s really nothing to say. We both know the deal. He knows; I know. I’d rather just forget.”
A billboard featuring 2025 Oscars host Conan O’Brien towers over Hollywood Blvd, in Los Angeles – REUTERS
By 2016, O’Brien was definitely over it, he told the Washington Post. “There was a period of my life where I was just trying to wrap my mind around . . . ‘What the f— happened there?’ ” he said. “Now enough time has gone by, and a big part of the process of getting over it was making new stuff I was proud of… now I rarely think of it.” Even in 2022, he was telling AdWeek that the whole thing was “screwed up.”
“I’m not sure Conan will ever completely forget the way he was treated,” according to one writer – who preferred to remain unnamed but who worked with O’Brien for a number of years. “There’s still some viciousness under the surface.”
Revenge may be a dish best eaten cold, but it’s even better its consumed live on air in front of millions of people around the world. You get the sense that Jay Leno knows this very well. “I was asked twice…” he claims, sounding like a kid on a playground who knows he’s beaten. Conan is back, although it took a very long time to get here.
