Bonus: A Couple of Quick Comments About Conan!

Late night television was one of my great delights growing up.

I know that in 2025, this is roughly equivalent to a wizened Depression-era grandfather wistfully reflecting on chasing a hoop around with a stick as a young lad, but it’s my truth.  I probably went to bed watching a late night show for a good ten years straight.  The structure of them brought me a lot of comfort during those inherently unstable teenage/college years.  Most of them went along the following lines: jazzy theme song, host monologue, bit, A-Block Guest Interview Part 1 & 2, second bit, B-Block Guest, musical/stand-up guest, goodnight.  What a given host wanted to do within those confines was up to them, and that’s what made it exciting.

Like most of my early interests, I picked up my penchant for late night from my mother.  Undoubtedly having grown up surrounded by The Tonight Show with Johnny Carson, my mom transitioned into watching the Leno iteration as well, so that’s what I initially became familiar with.  And, yeah, Leno has essentially spent the last three-plus decades burning any potential legacy he had earned back in the 80’s as (believe it or not) kind of a rogue-ish, sarcastic cultural commentator by honoring opportunity over literally anything else.  But at eleven years old, he served as a pretty great introduction into what could be comfy about late night television.  

Because he was uniquely a stand-up comedian at heart, the monologue was the only part of the gig Leno ever really cared about.  Thus, The Tonight Show always opened by playing to his strengths (and it’s no coincidence that the monologue was always the longest part of the show, pushing ten minutes with regularity).  Him doing what he did best first gave him a lot of grace as he pushed his way through fish-in-a-barrel skits like “Headlines” (oh, no, a newspaper has a typo!) and “Jaywalking” (hey, we ambushed someone on the street and they weren’t able to answer a question correctly!) and celebrity interviews of varying quality.  When he really hit, he made his own headlines (asking Hugh Grant what the hell he was thinking, asking Kanye West what his mother would have thought of him interrupting Taylor Swift*).  Most of the time, though, it was just ceding the floor to Hilary Swank or Denzel Washington or whoever to plug their new movie.

*Technically, this happened on the 2009 TV program The Jay Leno Show, but it was basically the same thing.

There’s a reason the cultural footprint of the Leno iteration of the Tonight Show is minimal; full archives on the Internet are really difficult to come by, likely because nobody was in a hurry to record it at the time.  It just wasn’t a program meant to exist beyond the hour a weeknight it was on.  But, Leno was never trying to reinvent comedy in the first place.  He was trying to put on an old-fashioned show, and I still admittedly respect that about him to this day.

Jay Leno was never cool, but he was functional.  

I open with all of this Tonight Show talk in order to simulate the grand broadcasting tradition of making people deal with Jay Leno first before moving on to the more interesting topic of Conan O’Brien.  

Because for coolness, you needed to wait until The Tonight Show wrapped at 12:35 am, and the next show began to air.

———

While watching the Kennedy Center ceremony for Conan O’Brien’s awarding of the Mark Twain Prize, I thought a lot about Late Night with Conan O’Brien. 

The reason for that is immediately obvious: bits and characters from Conan’s iteration of the landmark show, initially created and hosted by David Letterman, are constantly evoked on the Netflix version of the ceremony.  It opens, naturally, with the Masturbating Bear, perhaps the character that most exemplifies the “smart stupidity” ethos of Conan’s career (it’s a guy in a just-cheap-looking-enough bear suit, performing something that almost resembles masturbation).  But there are further surprise character appearances.  Triumph the Insult Comic Dog took on the emcee role.  Nikki Glaser squared off with the Interruptor.  Pimpbot 3000 whizzed by during a montage.  Incredibly, the FedEx Pope made his way to the stage.  All you needed was the Christmas Potato and the whole gang would be there.  Conan has had many stations in his career, but Late Night is where his persona was truly formed.

But it’s also bizarre to see this silly little show that played in the background of hundreds, maybe a thousand, nights of my life become this…legacy program.  To have the Max Weingberg 7 reunite on the Kennedy Center stage and have the same gravity as Doc Severinsen and the gang getting together one last time is just…indescribably strange.  Part of this strangeness is simply grappling with the linear passage of time; whether I like it or not, there’s a whole generation of comedy fans who look to Conan simply as an icon because they weren’t alive when he wasn’t.  But…frankly…watching Late Night as it was happening…it never crossed my mind that it would become this feted, legendary cornerstone of comedy.  I was honestly just happy it was able to exist at all.  

Late Night with Conan O’Brien felt miraculous during the era I was able to enjoy, and that’s not even counting its early years (that I was too young for) where, as John Mulaney pointed out in his Kennedy Center set, it was hanging by a constant series of thirteen-week renewal strings.  By 2001/02 or so (when I became a regular viewer), its security was in place.  But, the comedy was so silly and bare-bones at times that it still resembled basically nothing else on TV.  A guy dressed as Frankenstein running around the set, wasting time?  The playing of Walker, Texas Ranger clips?  A character named Preparation H Raymond?  It’s hard to imagine the ringleader in the middle of this nonsense ever being viewed in the same way as Johnny Carson.

But…here we are, Conan O’Brien being celebrated with the now-prestigious* Mark Twain Prize, the same award won by such comedic luminaries as Richard Pryor, Carl Reiner, Lorne Michaels, Lily Tomlin, Tina Fey, and George Carlin (and Jay Leno, sssh).  And why shouldn’t he be?  In 2025, I’m hard-pressed to come up with a comedian who’s been around as long as he has, and as beloved as he’s become.  

*Despite it only being recently invented in 1998.

It’s hard for me to reconcile the present view of Conan, this guy whose silly comedy was always well-liked and respected with my teenage/college years understanding of him, as a guy whose comedic sensibilities were genuinely questioned when he briefly made the move to 11:30, in his own stint as Tonight Show host.  Whose eventual move to (*gasp*) basic cable was looked at with a little skepticism back in 2010.  Whose 2019 venture into the world of celebrity podcasting came with a little risk, a possible devaluing of the Team Coco brand.

And, of course, at each step, he was able to learn and adapt while also keeping his own unique spirit at the forefront of everything he did.  Now, in 2025, there’s not a soul under the age of 50 who thinks Leno’s brand of late night was superior to Conan’s.  It’s become evident, as well, that his stint with TBS’ Conan and his podcast Conan O’Brien Needs a Friend has only grown his audience, not receded it; there are people younger than me who know him exclusively from those shows, not from his NBC run, or his run as an influential writer on Saturday Night Live or The Simpsons.  And the thing is…they like him just as much as I do, if not more.  It’s an astounding thirty years of consistency and longevity.

And he’s done it essentially without a single bad word said about him!  I know exactly one person who ever had a negative experience with Conan, and it’s not much in comparison to others of his ilk (it basically boils down to “he was a little stand-offish and dismissive after a taping”).  Beyond that?  No celebrity or civilian has had much in the way of tea to spill.  Who ever really knows what our public figures are really like (and I’m sure he’s been a dick at work in moments of pressure and crisis, as are we all), but…it would be more than a little surprising if something career-ending came out about him at this point.

(Can’t wait for that last paragraph to come back and haunt me!)

I suppose it’s always weird when your contemporary idols and influences eventually become “legends”; just ask 70’s rock-and-roll fans.  It’s likely to be a lifelong adjustment (just wait until the aforementioned Mulaney reaches his golden years and wins an award like this…it’s coming!).  But when it’s a guy like Conan?  Who’s in his early-sixties, has been working in the industry for over half his life, and still seems like he’s just getting started?

It makes it so much easier to bear.  Like a little Preparation H over the soul.