If you subscribe to the notion that TBS is Conan O'Brien's Isle of Elba, then David Letterman's pending retirement may have seemed like the perfect opportunity for Coco to rise again on network television, righting the wrongs done to him back in 2010 when NBC took The Tonight Show away from him.
It would have been the perfect story: the people's champion, rising then falling and rising again to glory. The trouble is, Stephen Colbert quickly snatched up the Late Show job and O'Brien never actually wanted it - which is good, because he doesn't need it.
Speaking to reporters to promote last night's turn as host of the MTV Movie Awards, O'Brien praised Letterman's eventual successor before addressing the speculation that he had wanted to follow in Letterman's footsteps once more.
“I wasn’t up for it. I’m very happy where I am, but I love Stephen. I think Stephen is great. [...] Whenever I would hear there was speculation (that I’d take over the Late Show), I was like, ‘No. What?’ I’m happy. [...] I get to do what I want.”
That contentment and creative freedom is apparent when you watch Conan, but while O'Brien's show is clearly back to firing on all cylinders - standing out as one of late night's most consistently funny, unique and bold entries - it has clearly been forged by the fires of a career that has experienced plenty of uplifting successes and one humbling failure - the loss of The Tonight Show.
Whether the fault of that failure belongs to O'Brien or NBC is up for debate. Some have said that Jay Leno's 10 o'clock show undercut The Tonight Show and that O'Brien's 16 years as the host of Late Night should have earned him more patience from NBC, while others point to the bland comedic makeover that occurred when O'Brien transitioned to The Tonight Show as a reason for the show's failure to hook viewers. At this point, however, it seems likely that all sides bear some of the blame.
To be fair to O'Brien, though, some kind of comedic style change away from the unruly sensibility of Late Night was inevitable - it was just a shock to the system to see it come on in a way that felt so rapid and unnatural.
The Late Night Era
As Jerry Seinfeld observed on the second episode of Jimmy Fallon's Tonight Show, these late night show's are something like a time capsule, wherein these hosts enter young and leave old. Along the way, we watch as they mature and as their taste's and even their abilities change. David Letterman, for example, stopped throwing himself at a velcro wall long ago; his show changed over time and so did he. There is no blown up TV Guide cover in the attic, ageing and crumbling as these hosts stay forever young.
When we met Conan O'Brien in 1993 he was barely 30 years old and shaking like a leaf in his first appearance as the host of Late Night. There was no polish and no experience for him to draw from as a rookie performer whose primary skills manifested themselves when he had a pen in his hand.
Early episodes of Late Night - while brimming with life and a reckless attitude - should be watched in slow-motion so as to not be distracted by O'Brien's rapid and nervous delivery - a bad habit that was surely helped by the constant threat of cancellation that hung over the young hosts head like the sword of Damocles, and the challenge of following David Letterman. That challenge is something that O'Brien took on during the cold open of his very first Late Night episode when he introduced himself to America by cheerfully preparing a noose for himself after numerous strangers angrily demanded that he be as good Letterman - a bold, absurd and self-deprecating introduction that has set the tone for O'Brien's entire career.
Though those early years were often populated by an undisciplined, buckshot approach to comedy, O'Brien and Andy Richter (his sidekick) eventually developed an easy chemistry and a confidence that both emboldened them and allowed them (with the help of writers like Bob Odenkirk, Robert Smigel, and Louis CK) to put their own spin on the Late Night brand and on late night itself.
For almost ten years, from 1994-2004, Late Night with Conan O'Brien enjoyed a golden era that was populated by "fire shows" ( where O'Brien and Richter filmed the show on the street in front of 30 Rock after a fire), an episode that was inexplicably performed in front of an all-kid audience, a claymation episode and time travel week.
This is the time of "shooting guns and drinking hard liquor" with Hunter S. Thompson, Old Time Baseball, the "Walker Texas Ranger Lever", Triumph, The Year 2000 (which later turned into The Year 3000, complete with fancier costumes for The Tonight Show despite the charm of the bits lo-fi nature and dated title), and countless other timeless bits and characters.
All good things come to an end, though, and eventually Conan's Late Night show started to gradually feel just a little bit safer, shaking all but the occasional flashes of greatness to live in a constant state of good; a wave that carried the show from the mid-aughts to the moment when O'Brien set off on his doomed stint as the host of The Tonight Show.
Losing The Tonight Show
There is no need to re-hash the whole affair, but it's clear that when O'Brien stopped trying to be more mainstream and started channeling some of his own anger over his deteriorating employment situation, he re-found his comedic sense of recklessness and it buoyed him at a time when he had nothing to lose that wasn't already being taken from him. But while O'Brien's upfront attitude about the awkward NBC situation and stunts like the Bugatti Veyron Mouse - an unimaginably expensive character that O'Brien claimed NBC would have to pay for - generated hearty laughs, O'Brien's finest hour on The Tonight Show occurred when he displayed enviable grace during his closing episode.
Like Johnny Carson's Tonight Show farewell, O'Brien's final message to his audience stands out as one of the most emotionally affecting moments in show history, impressively featuring kind words for NBC and a warning about cynicism - something that O'Brien publicly abstained from as he watched Leno retire and Jimmy Fallon take over The Tonight Show amidst a flurry of praise.
As we have now seen, unlike O'Brien, Fallon is an effortless and perfect match for The Tonight Show. Yes, O'Brien "deserved" the job and he is an immensely talented comic and late night host, but it takes more than want, smarts and skill. There needs to be an organic tonal fit to do that show and live up to its awe inspiring and restrictive history and O'Brien's time as host on The Tonight Show felt in-organic and forced. With more time, O'Brien's Tonight Show might have un-clenched its fists, but it still would have struggled to feel right. As is said, you can make a round peg go into a square hole if you have a mallet, but it just shouldn't be that hard.
On TBS, Conan seems easy by comparison and O'Brien seems free when he is on the air, embracing his right to preach to an earlier audience and the challenge of doing it in a way which - after a somewhat rocky start - feels true to his natural sensibility without the crippling expectations that come with The Tonight Show job.
Is that sensibility the same as it was on Late Night? Not exactly; O'Brien has matured after more than 20 years on the air between NBC and TBS, but while there are differences, the comedic soul of Conan is clearly descended from Late Night and O'Brien's Tonight Show never really felt that way. More precisely, Conan now feels like a natural evolution from O'Brien's Late Night days, much in the same way that the early Late Show felt as if was a big brother to Letterman's Late Night show.
O'Brien is comfortable within his own skin now and ever-willing to invite chaos onto the show for the sake of both the audience's and his own amusement. Look at this clip from an episode in February when seemingly everything that could go wrong does.
While most late night hosts would have edited out this collection of flubs, O'Brien instructs his producers to leave it in. He plays with the moment. Once again, there is no polish, but while the brilliance that can come from random flailing is gone, it has been replaced by a surgically precise comic instinct that is born from experience. While other shows and hosts are tightly wound and heavily scripted, O'Brien still embraces the danger of "live" TV even though he has a safety net, and that attitude is infectious.
From the cast of Workaholics stopping by to perform their "Wizard Rap" or their "Ode to Best Friends", comics turned correspondents like Pete Holmes and Deon Cole, Parks and Recreation star and cult hero Nick Offerman reading tweets, and Ice Cube and Kevin Hart recent trip through L.A. with O'Brien - guests and other funny people seem very willing to play on Conan.
The Lyft Cab bit is now part of O'Brien's live remote legacy that has continued to grow on Conan; most recently with his trip to a charm school, his tour of the American Girl store, and a turn as a deputy that was filmed during a recent trip to Dallas that also featured the return of the "Walker Texas Ranger Lever" and a wrestling match between people in Texas, Alaska and Hawaii foam suits. But while O'Brien gets a lot of credit for how he deals with "real" people during those remotes, few compliment his growth as an interviewer.
The casual rapport that O'Brien has with repeat guests like Tom Hanks, Will Ferrell, Harrison Ford, Will Arnett, and Paul Rudd, and his instant ease with newer guests like Joseph Gordon Levitt and Anna Kendrick is enviable, putting O'Brien in the top tier of his peer group, but O'Brien also has the ability to branch out and conduct more serious interviews when the occasion calls for it.
When comedy legend Sid Caesar passed away at the age of 91, due respect was paid to the father of live TV sketch comedy, but O'Brien went a step further, asking director Mel Brooks - who had written on Caesar's seminal series, Your Show of Shows - on for a simple chat about Caesar that filled the screen with charm, funny stories, and appropriate reverence for the man who had passed.
There is no way that such a moment would have happened on Late Night with Conan O'Brien, but much like Letterman did over time, O'Brien has grown into the kind of host that can both chase laughs and ignore them when something better is on the table.
The New Elder Statesman
By this time next year, there will be no late night host on the air who has done it for as long as Conan O'Brien has, and yet, he is still relevant two decades into a full career that, at the risk of generalizing, has been as vital, addictive and influential to those below a certain age as Letterman's career has to those above it. This is evidenced by the Team Coco YouTube channel's 40 million view per month average, O'Brien's popularity on Twitter, his aforementioned turn as host of the MTV Movie Awards, and the welcome news that he is going to bring Conan to San Diego Comic-Con in 2015 for a week of shows.
The Letterman/O'Brien comparisons will likely never stop. Both are smart, irreverent, and willing to take chances. Besides those similarities, they have walked a common path. When Letterman walked away from NBC, he did so because NBC would not let him into the cathedral that was The Tonight Show. Letterman built his own cathedral on CBS and that is what Conan O'Brien has been doing on TBS, where he has clearly learned the virtue of such things.
Like Letterman, O'Brien's best show may not be enough to hold the top spot in the ratings, but in a pool so flush with talent at a time when the numbers are not exactly an ocean apart, ratings supremacy isn't the ultimate sign of victory in the newest iteration of the "Late Night Wars". Conan can be the best show, and as O'Brien replaces Letterman without actually replacing Letterman, late night's standard-bearer-in-waiting stands right in the middle of his second golden age as a battle tested and gifted icon who is happy, free and ready for that fight. Yes, Fallon may have the edge right now and Colbert may have the buzz, but it's a marathon not a sprint and Conan O'Brien has been getting better at this for more than 20 years.
Conan airs on TBS Monday through Thursday @11PM.