With the retirement of David Letterman in 2015, Conan O’Brien became the longest-working of all current late-night talk show hosts in the United States.

After almost 28 years on the air, in three different iterations, Conan O’Brien will walk away from doing a nightly talk show for the last time on Thursday.
Although he will return with a weekly variety series on HBO MAX in the coming months, this still marks the end of an era and feels like I’m saying goodbye to a friend.
When I was a kid, I was geeky, awkward, and comedy-obsessed, feeling like I had a weird sense of humour only a couple of my classmates shared.
But when “Late Night with Conan O’Brien” debuted on NBC on September 13th, 1993, and a young, lanky, fire red-haired O’Brien took to the stage, my 14-year-old self felt an immediate connection. It was like the show’s strange and off-brand humour was speaking directly to me, making me stifle laughter as I secretly stayed up night after night to watch it while my parents slept.
One of the more interesting things to look back on is the role Canada played in the show’s early success, which did not come easy. Critics panned it, the network threatened to cancel it, and audiences didn’t vibe with the humour.
O’Brien has stated many times over the years, while American audiences struggled to understand what he was trying to do, Canadians quickly embraced it. Both the show and O’Brien eventually found their footing, creating staple absurd bits like “In the year 2000,” “The Walker Texas Ranger lever,” “Satellite TV,” and so many more.
With characters like “Triumph the insult comic dog,” “Pimpbot 5,000,” “Preparation H Raymond,” – and a certain bear I can’t mention – all making regular appearances, equally delighting studio audiences and those at home.
One of my all-time favourite reoccurring bits featured a pre-Saturday Night Live Amy Poehler in the audience playing Andy Richters little sitter, Stacey, who was obsessively in love with Conan. Almost every sketch ending with an enraged Poehler charging onto the stage to beat up Andy, and pounce on Conan.
It was these characters, sketches, and moments that made Conan stand out from his counterparts David Letterman and Jay Leno. His commitment to ridiculous premises and preposterous created hilarious moments.
But it wasn’t just the bits. Conan himself became a star.
To me, one of the many things that made him so endearing to audiences is his ability to be self-deprecating. While David Letterman took on the role of a smug character, and Jay Leno played it cool, Conan leaned into his geeky, lanky, awkwardness in the absolute best way possible. He always found ways to poke fun at himself and become the butt of the joke, which got laughs and made him seem more accessible and relatable to the audience at home.
He wasn’t too cool for school, which made me, and so many others like me, who never came anywhere close to being cool, suave, or smooth, feel like one of our own was on TV every night, killing them with kindness and hilarity.
However, along with the self-deprecation and comic genius, there is sincerity to OBrien. Moments where Conan would go into serious mode, and you could see the real genuine compassion come out, like when he paid tribute to comedian Chris Farley on the day he died, with Conan choking up as he talked about the passing of his friend.
Undoubtedly, Conans most famous moment of being real came during the final goodbye of his last episode of “The Tonight Show,” which he hosted for just seven months before he and NBC very publicly parted ways.
At what was the most difficult moment of his career, O’Brien very graciously showed gratitude for his 20-year stint at the network and left fans with sincere advice.
“Please do not be cynical. I hate cynicism. For the record, its my least favourite quality. It doesnt lead anywhere. Nobody in life gets exactly what they thought they would get. But if you work really hard, and youre kind, amazing things will happen.”
A quick note of recognition to Andy Richter, who, minus a few years, has been by Conan’s side the entire way.
Richter has played the role of sidekick, but really, felt more like Conans best friend, who was there with him to deliver perfectly timed jokes and laughs; often at his own expense. There is no Conan without Andy, and there is no Andy without Conan.
You’ll often hear people who were teenagers and twenty-somethings in the ’70s talk about the reverence they have for Johnny Carson. People of the same age in the ’80s hold David Letterman in similar regard.
If you were in your youth or a young adult in the 90s and early 2000s, Conan OBrien was that guy, and his show was that show. The one you would quote with your friends the next day at school, the one whose bits and characters became your favourites.
On a personal level, I’ve always been obsessed with comedy, with dreams of being a comedy writer.
While I had fantasies of maybe writing an episode of the Simpsons or coming up with sketches for SNL, the real ultimate desire was to be on the writing staff for Conan.
In 2004, I was lucky enough to win the ticket lottery to see a live taping when Conan brought his “Late Night” show to Toronto, done in part as a way to thank Canadians for their early and ongoing support of the production.
Getting to be a part of the rambunctious crowd cheering on the ridiculous antics of my comedy idol is a moment I will always cherish.
Conan has come a long way from the 30-year-old complete unknown, plucked out of The Simpsons and SNL writers rooms, to becoming a veteran late-night talk show host and a cultural icon. Between “Late Night,” “The Tonight Show,” and “Conan” on TBS, O’Brien has been at the pinnacle of late-night television for three decades.
While the Jimmy’s (Kimmel, Fallon, and Corden), Stephen Colbert, Seth Meyers, Lilly Singh, and others still remain as late night hosts on network television, O’Briens departure does mark somewhat of a beginning of the end of traditional late-night shows.
Young Millennials and Gen Z are frequently, if not entirely, getting their entertainment from non-traditional mediums like Tik Tok and YouTube, where a new generation of stars have risen to prominence. Late Night shows may still be around for years to come, but they likely will never be the same powerhouse, cultural shapeshifters they have been in the past.
It will be strange not seeing Conan on my TV every night, but at least I’ll still be able to re-watch my favourite moments online forever (Look up Conan gives Tom Hanks a birthday present. One of my all-time favourites).
For now, we will all have to live with hearing Conan on his weekly podcast, which has brought out another hilarious side of O’Brien and has become a weekly listening ritual for his fans, both old and new.
It’s ironic the podcast is called “Conan OBrien Needs a Friend” because it certainly feels like he’s an old friend of mine; one who has been in my living room every night, making me laugh, for 28 years.