(CNN)Almost 30 years after becoming the “new guy” in late-night TV, Conan O’Brien is closing that chapter of his life. And while the key players associated with his long, strange odyssey made out better than fine, that doesn’t mean the red-haired host wound up where he wanted to, or that the ride hasn’t been a roller coaster.
Having followed O’Brien’s arc from the beginning, it’s hard to believe he’s become such a part of the cultural firmament. As a reminder, he was tapped to fill David Letterman’s old slot at NBC in 1993, when Letterman jumped to CBS after losing out to Jay Leno in the first “The Tonight Show” succession battle.A 30-year-old unknown comedy writer when making his debut, O’Brien survived cancellation several times in the early going. NBC kept renewing the show in 13-week increments, underscoring its lack of faith, before he became such a valued player that the network anointed him to replace Leno, only to result in a scenario as messy as the first one.
All roads in late night seemingly lead to “Tonight,” and the giant shadow that Johnny Carson cast over the TV landscape. The “Late Night” slot that Letterman launched in 1982 created what amounted to a farm team for hosts eager to be promoted to Johnny’s desk, creating a binary choice where keeping one talent happy meant disappointing another who might jump to a rival network.
While O’Brien’s comedic sensibility leaned closer to Letterman’s than that of his lead-in, Leno, he similarly coveted the marquee slot. That prompted another tough decision for the network that had gone with Jay instead of Dave, a choice documented by CNN contributor Bill Carter in his book “The Late Shift.”Read MoreIn 2004, NBC sought to mollify O’Brien — who was fielding offers from other networks — by promising him “The Tonight Show” in five years, when Leno’s contract expired, presumably enough time for Leno to complete his run and formally pass the baton.
Photos: Conan O'Brien's late-night careerConan O’Brien is seen backstage on the set of his show “Conan” in 2019. He’s been a late-night host for nearly 30 years.Hide Caption 1 of 25
Photos: Conan O'Brien's late-night careerConan O’Brien is seen backstage on the set of his show “Conan” in 2019. He’s been a late-night host for nearly 30 years.Hide Caption 2 of 25
Photos: Conan O'Brien's late-night careerO’Brien is the guest as he appears on “The Tonight Show with Jay Leno” in 1996. In 2009, O’Brien would replace Leno as “The Tonight Show” host — at least for a short while.Hide Caption 3 of 25
Photos: Conan O'Brien's late-night careerO’Brien does a skit with his longtime show sidekick, comedian Andy Richter, in 1996. Richter has been a part of O’Brien’s show for much of his late-night run.Hide Caption 4 of 25
Photos: Conan O'Brien's late-night careerO’Brien delivers a monologue as he hosts an episode of “Saturday Night Live” in 2001. Before he became famous, O’Brien was a writer for the show.Hide Caption 5 of 25
Photos: Conan O'Brien's late-night careerO’Brien warms up the crowd at one of his “Late Night” tapings.Hide Caption 6 of 25
Photos: Conan O'Brien's late-night careerO’Brien takes a photo of Microsoft co-founder Bill Gates during the Consumer Electronics Show in 2005.Hide Caption 7 of 25
Photos: Conan O'Brien's late-night careerO’Brien hands a Valentine’s Day present to Finnish President Tarja Halonen as he visited the presidential palace in Helsinki in 2006. O’Brien’s resemblance to Halonen became a recurring bit on his show, and he eventually traveled to meet her and do a special episode from Finland.Hide Caption 8 of 25
Photos: Conan O'Brien's late-night careerO’Brien jokes around with fellow talk-show hosts Stephen Colbert, left, and Jon Stewart during a “Late Night” episode in 2008.Hide Caption 9 of 25
Photos: Conan O'Brien's late-night careerO’Brien does a Christmas segment with boxing legend Mike Tyson and longtime show performers Andy Richter and Max Weinberg in 2009. O’Brien replaced Jay Leno as host of “The Tonight Show” earlier that year, but he didn’t stay there for long.Hide Caption 10 of 25
Photos: Conan O'Brien's late-night careerO’Brien is joined by Triumph the Insult Comic Dog, one of his show’s most iconic characters, in 2009.Hide Caption 11 of 25
Photos: Conan O'Brien's late-night careerO’Brien’s last episode of “The Tonight Show” aired on January 22, 2010, less than a year after he started. With ratings flagging, NBC wanted to move Jay Leno back into late night and push “The Tonight Show” to a later time slot to accommodate Leno’s new show. O’Brien refused the time change and left. But during his farewell show, O’Brien had a hopeful message for his audience. “All I ask is one thing, and I’m asking this particularly of young people that watch: Please do not be cynical,” he said. “I hate cynicism. For the record, it’s my least-favorite quality — it doesn’t lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you’re kind, amazing things will happen.” Hide Caption 12 of 25
Photos: Conan O'Brien's late-night careerO’Brien appears on Letterman’s show in 2012. They discussed O’Brien’s short-lived stint as host of “The Tonight Show” and had some fun at Jay Leno’s expense.Hide Caption 13 of 25
Photos: Conan O'Brien's late-night careerO’Brien jokes with President Barack Obama as he hosted the White House Correspondents’ Association dinner in 2013. It was O’Brien’s second time hosting the event. He also hosted in 1995.Hide Caption 14 of 25
Photos: Conan O'Brien's late-night careerO’Brien hosts the MTV Movie Awards in 2014.Hide Caption 15 of 25
Photos: Conan O'Brien's late-night careerO’Brien wears a bomb disposal suit as he taped episodes of his “Conan” show in Qatar in 2015. O’Brien traveled to Qatar along with first lady Michelle Obama, and he also entertained US troops who were stationed there.Hide Caption 16 of 25
Photos: Conan O'Brien's late-night careerO’Brien dances in Cuba in 2015. He became the first American late-night host to do a show in Cuba in more than 50 years.Hide Caption 17 of 25
Photos: Conan O'Brien's late-night careerO’Brien speaks on stage during a gala tribute to comedian Steve Martin in 2015.Hide Caption 18 of 25
Photos: Conan O'Brien's late-night careerO’Brien poses for a photo with journalist Jorge Ramos as they walk in Mexico City in 2017. O’Brien taped an episode of his show in Mexico to “do something positive” after the tensing of US-Mexico relations.Hide Caption 19 of 25
Photos: Conan O'Brien's late-night careerO’Brien fist-bumps basketball legend Shaquille O’Neal during a Turner Upfront show in 2017.Hide Caption 20 of 25
Photos: Conan O'Brien's late-night careerO’Brien tapes a segment while visiting Japan in 2018.Hide Caption 21 of 25
Photos: Conan O'Brien's late-night careerO’Brien goofs around with Stephen Colbert while appearing on “The Late Show” in 2019.Hide Caption 22 of 25
Photos: Conan O'Brien's late-night careerO’Brien visits Ghana with his show in 2019.Hide Caption 23 of 25
Photos: Conan O'Brien's late-night careerO’Brien does a segment about “The Two Popes” in 2020.Hide Caption 24 of 25
Photos: Conan O'Brien's late-night careerO’Brien’s last “Conan” show will air on June 24, 2021. The show has been on TBS since 2010.Hide Caption 25 of 25
For a time, NBC looked like it had found a way to keep both guys and maintain peace and harmony. But as the actual date neared, Leno showed no signs of slowing down or interest in retiring and became a threat to set up shop elsewhere.What happened after that has been well-documented, but long story short, NBC gambled on moving Leno into prime time, then scuttled the experiment and opted to return him to “The Tonight Show” time period.Understandably miffed, O’Brien jumped to TBS in 2010. Over the past decade, he has offered the same brand of smart comedy on a lower-profile, basic-cable platform. When Leno eventually stepped aside, Jimmy Fallon took over.As CNN’s recent docuseries “The Story of Late Night” made clear, the ill feelings from that outcome haven’t faded, although the exercise in choosing sides — with Leno again cast as the bad guy — and the “Team Coco” campaign launched by O’Brien’s admirers always felt a bit overwrought. With the benefit of hindsight, NBC’s dice roll on when Leno would be ready and willing to retire merely postponed losing one of its hosts. But O’Brien left NBC with a massive payout and migrated to a new home that appreciated and showcased his talents.The small club of successful late-night hosts have a knack for endurance. Leno works constantly (and has said he doesn’t miss “Tonight” in the current era), Letterman resurfaced doing one-on-one chats on Netflix, and O’Brien’s signoff isn’t so much a goodbye as a change of venue, with TBS specials and an HBO Max variety series in his future. (Like CNN, TBS and HBO Max are units of WarnerMedia.)As he has reminisced this week, a relaxed O’Brien — who even shared a joint with Seth Rogen — appears nostalgic, but also content about giving up the daily grind, in much the way Jon Stewart sounded leaving “The Daily Show” after 15 years.During his final “The Tonight Show” episodes, O’Brien delighted in skewering NBC and Leno, at one point wryly telling kids, “You can do anything you want in life. Unless Jay Leno wants to do it, too.”
O’Brien didn’t get to keep the job he’d always wanted, and fans will forever feel that he never really had a fair shot. But for a host who almost didn’t last two years at NBC, it’s been a pretty remarkable run.The final “Conan” airs June 24 at 11 p.m. ET on TBS.
Source: edition.cnn.com
