A Fond Farewell To Conan O'Brien's Late Night Run | Features | LIVING LIFE FEARLESS
GAGE SKIDMORE

A Fond Farewell To Conan O’Brien’s Late Night Run

I am now, and will almost always continue to be, a Conan Guy. The way so many people a little bit older than me considered David Letterman the comedic voice of their generation, I always felt the same way about his successor as the host of NBC’s Late Night, Conan O’Brien. 

Last week, Conan wrapped up his 28-year run as a late night host when he retired the current iteration of his TBS talk show. O’Brien will remain on television, doing some type of variety show on HBO Max, while he will continue to produce his Conan Without Borders travel specials and his “Conan O’Brien Needs a Friend” podcast. But this week will mark the end of his career as a late night host. 

The story is well known: In 1993, NBC plucked O’Brien from nearly complete obscurity to replace Letterman as the host of Late Night, after Dave jumped to CBS. Best known at that point as a writer for Saturday Night Live and The Simpsons, O’Brien had rarely been on camera, and those early days showed it. 

But around 1996, the Late Night show found its voice and rhythm, and really started to get good. That year also happened to be when I started college. 

Throughout the next four years, when we were all still young enough that it wasn’t a questionable proposition to stay up late enough to watch a show that starts at 12:30, my roommates and suitemates would watch on a nightly basis, and laugh and laugh and laugh. 

We laughed so hard, in fact, at some of those Triumph the Insult Comic Dog bits that we would literally wake up our neighbors. (Nearly 20 years later, I would wake up one of my kids laughing at a Triumph political special).

I’ve enjoyed Conan’s shows as they’ve evolved and switched networks, formats and time slots, but it really never got better than it did in that back half of the 1990s. 

It’s when we all were all introduced, of course, to Triumph, a bit so simple that it still hasn’t gotten old 25 years after its introduction: 

When I met Triumph, along with his puppeteer Robert Smigel, during a Democratic Natioanal Convention protest bit in 2016, it was one of my more exciting celebrity sightings:

The author wth Triumph the Insult Comic Dog and Robert Smigel, outside of Philadelphia’s City Hall in July of 2016.

I was partial, also, to the “Clutch Cargo” bit, especially with Arnold Schwarzenegger, who would always mention “the smash holiday classic Jingle All the Way“:

And of course, the Masturbating Bear: 

And the Guy Who’s Protected From Three-Inch Bees:

I always enjoyed the single appearance of the Dancing Gorillas and Quake Guy: 

I was always confused about the copyright legality of Vomiting Kermit: 

And perhaps my favorite moment in the early Conan days was the then-87-year-old actress Helen Martin who, while promoting her role a “pot-smoking granny” in the movie Don’t Be a Menace to South Central While Drinking Your Juice in the Hood, proclaimed “I love the reefer!”:

And of course, the Paul Rudd Mac and Me gag has somehow never gotten old: 

We all know, of course, how Conan’s NBC tenure ended. In 2004, O’Brien was announced as the next host of The Tonight Show, upon Jay Leno’s planned retirement in 2009. But 2009 rolled around, Leno’s show was still popular, and so NBC stuck Leno on at 10 p.m. five days a week, ahead of Conan’s Tonight Show at 11:30. When both experiments, failed, NBC proposed moving Leno to 11:30 for a half-hour show, to be followed by The Tonight Show at 12:05. 

As a result, O’Brien wrote the famous “People of Earth” letter. And despite the “Team Coco” campaign that followed, he soon agreed to leave NBC, ending up at TBS, which is where he’s been for the last decade-plus.

Since going to TBS, Conan has continued to do innovative things. His travel specials are always outstanding, and I was sure to watch his Conan in Cuba special before I traveled to Cuba myself:

Conan’s podcast also quickly became one of the best around, with the best episodes being the ones featuring old hands on his show like Bob Odenkirk. 

At the same time, a perusal of the recent CNN documentary The Story of Late Night just shows how ghastly and unfunny and insufferable late night television has become. There’s Jimmy Fallon and James Corden, whose shows are practically unwatchable (as Billy Eichner said on Difficult People, “isn’t it funny how Jimmy Fallon slowly turned The Tonight Show into a children’s birthday party?”).

The once-subversive Stephen Colbert now does something on CBS that barely resembles comedy at all; his best-received bit of the last few years appears to be the time he walked around the Republican convention dressed as a Hunger Games character. Most of the other shows are more devoted to “clapter,” and liberal political hectoring, which is tiresome even when I agree with said hectoring. All of these shows are way more about delivering viral videos than crafting a good 60-minute show.  Seth Meyers’ show is great, and John Oliver’s has its moments, but that’s about it.

Conan never turned into any of that. While he’s certainly changed over the last 30 years, his comic sensibility always stayed true to what it always was. And while Conan will remain a part of our lives, I’m going to miss him in late night. 


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