In the Cone Zone
When I was 14, I made a big change. I moved out of the small bedroom I had called home my entire life, taking my belongings down the hall to the bedroom vacated by my sister Andrea, who had graduated from college and was off on her own.
This room was an upgrade in almost every conceivable way. It had two windows, two beds, a phone, and its own thermostat from which to manage the temperature in our perpetually freezing house.
My old room did not have these things.
Most important, though, was that the new room had a cable television set. Finally, I could live out my dream of watching TV 24 hours a day without leaving my bed. And although it was physically impossible to do so on a daily basis, I sure gave it my best shot.
That summer of 1993 witnessed one of the great upheavals in the history of late night television, a genre I had heard about but hadn’t seen in my TV-less bedroom. Now, with a little ingenuity, I could watch the drama unfold until all hours of the night without my parents noticing.
Johnny Carson had retired as the host of NBC’s The Tonight Show, and Jay Leno had landed the coveted role as his replacement. Johnny’s presumed heir, David Letterman, angrily left NBC’s Late Night for a new show on CBS that would compete directly with The Tonight Show.
Into the void on Late Night stepped a virtually unknown 30-year-old with red hair and a funny name: Conan O’Brien.
If Johnny belonged to my parents’ generation and Dave was for my older siblings’ generation, Conan was going to be my guy.
He was young and self-deprecating, his comedy was weird and filled with strange characters, and his bandleader was Bruce Springsteen’s drummer, Max Weinberg. Plus he had written for my favorite show, The Simpsons, so he needed no further credibility in my book.
I was all in, whether I watched the show as it aired at 12:35 am or recorded it on a VCR and watched after school the next day.
Unbeknownst to me, in the early days of the show, network executives — and apparently other viewers — were less enthusiastic about Conan’s comedy, and his tenure as host almost came to an end. But I loved the way he made fun of himself with the help of his sidekick, Andy Richter. I loved the bizarre characters like Carl “Oldy” Olsen, the Masturbating Bear, and Pimpbot 5000. And I loved bits like “In the Year 2000,” which envisioned all the outlandish things that would happen in the impossibly far-off future of that mystical, millennial year.
Every night that I tuned in, I never knew what I was going to see on Late Night. But I knew it was going to be fun. And I became a devoted viewer and fan.
Conan survived his rocky first season and went on to host Late Night for 16 years. NBC famously gave him The Tonight Show in 2009, then infamously took it away after seven months. He later turned up at TBS, where he hosted Conan from 2010-21.
In the years after I went to college, I continued to follow his career but didn’t watch his show quite as obsessively. When he launched the podcast Conan O’Brien Needs a Friend in 2018, though, I experienced a Conan-aissance. In this one-on-one interview format, I discovered Conan’s wit, improvisational skills, and intelligence coming through in ways that traditional television could sometimes stymie. I haven’t missed a single episode since its debut.
In addition to listening to the podcast as usual this past week, I suddenly found myself awash in Conan-related content — an entertaining mix of inventive comedy, fun interviews, memorable music, and a few slices of television history (as I explain below). Engaging with all of it was a great way to spend some time during the holidays.
(I should also mention that Conan had dinner down the street from me last week at Modern Apizza.)
My parents sold our house more than 20 years ago, so I haven’t been in that old bedroom in a very long time. But whenever I watch or listen to Conan, I’m transported back to that place. And a part of me turns into the 14-year-old kid who couldn’t wait to stay up late and find out what wackiness awaited him.
The Best…
…Conan Documentary I Watched This Week
Conan O’Brien Can’t Stop (2011) — Directed by Rodman Flender
Streaming with subscription on Amazon Prime Video; available for rent on other streaming platforms
In the months following Conan’s ouster from The Tonight Show, he was legally prohibited from appearing on television. So in search of the approval of strangers, he took his talents on the road, performing a comedy and music show for fans across the country.
Conan O’Brien Can’t Stop is a behind-the-scenes look at that tour and Conan’s state of mind after he unceremoniously lost his dream job. Of particular note is the emergence of Conan’s assistant, Sona Movsesian, as her boss’s comedic foil — a dynamic that has become a key feature of the podcast. (Thanks for the tip, reader Mark L.)
…Conan Oral History I Read This Week
“You Better Be as Good as Letterman!” Conan O’Brien’s Wild First Year: An Oral History — By Andrew Buss, Vanity Fair, December 20, 2023
In this oral history of Conan’s first year at Late Night, some of the people who were there take a look back at the unlikely decision to replace Letterman with Conan, and the tumultuous year that followed.
…Classic Conan Field Piece I Watched This Week
“Triumph Attends the Premiere of Star Wars: Attack of The Clones" — Late Night with Conan O’Brien, May 17, 2002
Five years after Robert Smigel invented “Triumph the Insult Comic Dog” for Late Night, the legendary writer and producer created his magnum opus: “Triumph Attends the Premiere of Star Wars: Attack of the Clones.” Many more Triumph field pieces would air on Late Night, but this one remains the classic among classics.
…Christmas Tradition I Continued This Week
“Bruce Springsteen - Merry Christmas Baby” — Late Night with Conan O’Brien, December 11, 2002
Watching this video is admittedly my only Christmas tradition, and I can’t get enough of it. Every year on the big day, I play it no fewer than 10 times.
Bruce’s ridiculous performance. Conan looking understandably stiff and kind of scared. Clarence’s leather pants. Santa almost running over Patti. Max’s soft hands when he catches his “present.” Phantom Danny on the organ. The revival of the Miami Horns. The dancing audience members. And Bruce’s deadpan closing line: “Well done, Santa.” The whole thing just kills me. I encourage you to consider making it a Christmas tradition in your home, too.