Conan O'Brien RULES!

Nick Digilio
11 minutes ago
7 min read

Conan O’Brien is one of my favorite comic voices of all time, and I think at this point we can safely stop referring to him simply as a late-night talk show host.

He is certainly one of the greatest late-night hosts ever, but the guy has now been doing this for so long, in so many different forms, that he has become something much bigger than that: a genuine American comedy institution.

And the wonderful thing is that he is still really, really funny.

With the third season of Conan O’Brien Must Go now arriving on HBO Max, I thought this would be a good time to dig into the archives and pull out some of my favorite Conan moments from over the years. Because this guy has had one hell of a career.

He has been a comedy writer, television host, performer, podcaster, travel-show host, occasional actor, awards-show host and professional giant redheaded idiot for more than 35 years. And I mean that last description with tremendous affection.

Conan Christopher O’Brien was born in Brookline, Massachusetts, in 1963, and this is a guy who was clearly headed toward writing from a very early age. He was valedictorian of his high school class, went to Harvard, majored in history and literature, graduated magna cum laude and, most importantly for what came later, wrote for and eventually became president of The Harvard Lampoon.

He even played drums in a band called the Bad Clams, which sounds exactly like the name of a band Conan O’Brien should have played drums in.

After Harvard, he moved to Los Angeles and wrote for the HBO comedy series Not Necessarily the News, took improv classes at the Groundlings and eventually landed on the writing staff at Saturday Night Live in 1988.

He worked there for three years, winning an Emmy with the writing staff, and during the 1988 writers’ strike he spent some time right here in Chicago, performing an improv revue called Happy Happy Good Show with fellow SNL writers Bob Odenkirk and Robert Smigel. He even briefly shared an apartment near Wrigley Field with Jeff Garlin.

So, you know, there's a little Chicago in Conan.

His SNL years were important, but then he moved over to The Simpsons during one of the greatest periods in the history of that show, and some of the episodes he wrote are classics. Conan wrote “Marge vs. the Monorail,” which is simply one of the greatest Simpsons episodes ever made, as well as “Homer Goes to College” and “New Kid on the Block,” and he worked on “Treehouse of Horror IV.”

You can already see the Conan sensibility in those shows, the combination of intelligence and complete stupidity, the love of absurdity, the willingness to follow a ridiculous idea way past the point where any normal person would have stopped.

Then something happened that, looking back on it now, seems completely insane.

David Letterman left NBC for CBS after the infamous Tonight Show mess involving Jay Leno, and NBC needed somebody to take over Late Night. Instead of hiring an established comedian or television personality, Lorne Michaels helped select this gangly, pale, redheaded comedy writer that almost nobody in America had ever heard of.

Conan O’Brien got the job in 1993. Andy Richter became his sidekick, and Conan went from sitting in writers’ rooms to following David Letterman on national television. And initially, it was rough.

People forget this now. Late Night with Conan O’Brien was not an immediate success. The reviews were brutal. Conan was nervous and awkward, the ratings weren't great, NBC kept threatening to cancel the show and at one point the network reportedly had him working essentially week-to-week.

But something wonderful happened: Conan figured it out. More importantly, he figured out how to be Conan.

Instead of trying to become Letterman or Carson or anybody else, he leaned into his own weirdness. The show became stranger, sillier and more surreal. “In the Year 2000.” “If They Mated.” The ridiculous celebrity photographs with moving mouths. Preparation H Raymond. The Masturbating Bear.

And Robert Smigel, one of the great comedy writers and performers of all time, created Triumph the Insult Comic Dog, who became one of the funniest recurring characters in late-night television history.

The show slowly developed an intensely loyal younger audience, and Conan went from being the unknown guy everybody assumed NBC would fire to hosting Late Night for sixteen years.

There was also something else developing during those years that I think ultimately became Conan's greatest strength: the remote pieces. Put Conan behind a desk and he's very funny. Put Conan out in the real world with ordinary people and absolutely anything can happen.

That became an essential part of his comedy. Conan is extraordinarily quick, but he also understands that the funniest person in a comedy piece doesn't always have to be Conan O'Brien. He lets people be funny. He reacts to them. He makes himself the idiot.

He is completely willing to be embarrassed, insulted, humiliated or made to look ridiculous if that's where the laugh is. That quality eventually evolved into Conan Without Borders, where he traveled internationally, including trips to Cuba, Armenia, South Korea and numerous other countries. Those travel specials became some of the most popular and acclaimed work of his career.

Of course, there was also The Tonight Show. Oh boy.

Conan finally inherited The Tonight Show from Jay Leno in 2009, which was something NBC had promised him years earlier. It lasted seven months. Then NBC started screwing around with the schedule because Leno's prime-time show wasn't working, proposed pushing Conan's Tonight Show past midnight, and Conan basically said: No. That's not The Tonight Show.

He was right.

The entire thing became one of the ugliest and most ridiculous network television debacles ever, Conan left NBC, and Leno returned to The Tonight Show. Conan then took the beautifully titled Legally Prohibited from Being Funny on Television Tour around the country before resurfacing on TBS with Conan, which ran from 2010 until 2021.

And I loved the TBS show. In some ways, getting away from the enormous historical baggage of The Tonight Show ultimately freed Conan to become even more Conan. By the time Conan ended, he had been hosting late-night television for nearly three decades.

But what I really love is that he didn't simply disappear when traditional late-night television stopped being the center of the culture. He evolved.

Conan O’Brien Needs a Friend, which began in 2018, became one of the best and most successful comedy podcasts around. And the podcast revealed something that his television shows had occasionally demonstrated but couldn't always explore: Conan is a genuinely terrific interviewer.

He's curious. He's incredibly knowledgeable about comedy history. He listens. And because he is so quick, the conversations can suddenly turn into these extended improvised bits that are unbelievably funny.

Then there is Conan O’Brien Must Go, which takes everything that was great about the old remote pieces and expands it into a travel series. It is Conan interacting with people, cultures and situations he doesn't completely understand and turning himself into the butt of the joke. That's Conan at his absolute best.

He's even become a surprisingly effective actor. Most recently, he showed up opposite Rose Byrne in If I Had Legs I’d Kick You, playing her therapist, and he's remarkably good in it. It isn't some big goofy Conan cameo.

It's an actual performance, and another reminder that there's more range there than you might expect from the guy who spent years pulling imaginary strings on his hips and doing that ridiculous little dance.

And then there are the awards shows.

Hosting the Oscars is a brutal job. Everybody analyzes everything, half the audience is waiting to complain, the celebrities sitting in front of you can be terrified of becoming part of the joke, and somehow you have to keep a gigantic live television production moving while actually being funny. Conan has turned out to be terrific at it.

He hosted the Academy Awards in 2025 and 2026 and is scheduled to return in 2027; he's also hosted the Emmys twice and the White House Correspondents’ Dinner twice. In 2025 he received the Mark Twain Prize for American Humor and was inducted into the Television Academy Hall of Fame.

That's a pretty remarkable journey for the weird unknown writer NBC hired in 1993 whom everybody thought was going to be canceled.

What has always appealed to me about Conan is that his comedy can be incredibly smart and incredibly stupid at exactly the same time. He's a Harvard-educated guy who can talk intelligently about history, literature and the evolution of American comedy, and then five seconds later he is making a completely idiotic face, screaming in a ridiculous voice or committing to some absurd physical bit like his life depends on it.

That's a very specific comic voice, and nobody else really has it.

He survived brutal reviews, cancellation threats, network politics, the Leno fiasco, the decline of traditional late-night television and the complete transformation of the entertainment business.

He moved from network television to cable, from cable to podcasts and streaming, and somehow every transition has felt natural because the platform was never really the point.

Conan was the point.

He is one of the great comedy writers of his generation, a legendary late-night host, one of the best remote performers ever, a terrific interviewer, an enormously successful podcaster, a great awards-show host and, after all these years, still one of the funniest people around.

So, with the third season of Conan O’Brien Must Go here, I thought it would be fun to celebrate Conan with some clips from throughout his career. Some classic bits, some memorable moments and, basically, just some very funny Conan O’Brien stuff.

Enjoy.