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A Farewell to Conan O’Brien

June 26, 2021 | Posted by Steve Gustafson
Conan O'Brien

“I’ve devoted all of my adult life to pursuing this strange phantom intersection between smart and stupid. There’s a lot of people who believe the two cannot coexist, but god, I will tell you, it is something I believe religiously, I think when smart and stupid come together… I think it’s the most beautiful thing in the world.” -Conan O’Brien

When Conan O’Brien debuted on late night on September 13, 1993, he did so to poor ratings and even poorer reviews, with one critic saying he was “too smart, too East Coast, too sophisticated, too young and even too tall to be successful.”

To me, he was perfect. Yes, I was a fan from episode one because here was someone who spoke to my random, quirky self-depreciating style of humor. Conan exemplified something new to the late night scene, even if I couldn’t properly put it into words while I tried to explain this to my friends. 

Everyone has heard the stories about his first few seasons, where cancellation hung over him like the Sword of Damocles, but I laughed at every episode. I wasn’t hip on the behind-the-scenes workings but I’d hear things and it wasn’t until later that I found out how NBC threatened to put Conan on a week-to-week contract in 1994. And how executives were pushing to replace him with Greg Kinnear. And read stories how interns filled empty seats in the audience. And how affiliates seriously inquired about replacement hosts.

With all that going on, with unimaginable pressure, Conan continued to entertain his small, but slowly growing, core of fans. 

I was trying to put together a list of favorite skits and characters from Late Night but it’s simply impossible. I mean, you have ‘Conan Plays Old Timey Baseball’, ‘Conan Forms the Boy Band Dudez A-Plenti’.and ‘Conan Goes to Houston to Find Viewers’. How can you rank the Walker, Texas Ranger Lever, FedEx Pope, Artie Kendall the Ghost Crooner, Andy’s Little Sister, “No Reason to Live” Guy, The Interrupter, The Masturbating Bear, and Triumph the Insult Comic Dog?

Who knows? I still might try to do that list.

I thought maybe a list of his best guests but that to would be a folly. Even though I’d probably have Norm MacDonald as number one. Although Paul Rudd would be a close second.

Of course we have to mention Conan’s stint as host of The Tonight Show. While many loved what he did, the ratings didn’t reflect that and instead of giving time to let him adjust, he went on to better things. 
To say his time at TBS was filled with brilliance is an understatement. His remotes in other countries are must watch and prove his comedic stylings are shared internationally. He found a interview rhythm that was relaxed and brought out the best in guests. His skits with his staff are classics that bring a smile to your face. 

And if you aren’t listening to his podcast Conan O’Brien Needs a Friend, correct that immediately.

So after nearly 30 years and a lot of laughs, O’Brien said goodbye to late night on Thursday night. It was fitting that the final Conan opened with an animated O’Brien doing an exit interview with Homer Simpson. O’Brien was a writer on The Simpsons, writing one of my favorite episodes, Marge vs. the Monorail.

While he’s stepping away, he’ll be back doing a variety show on HBO Max in 2022 but in the everchanging world of late night, it’s the end of an era. Conan pushed the boundaries in new ways, showed possibilities on how to reach new audiences, and shined brightest when others thought that was impossible.

Share your favorite Conan skit, character, or memory below!

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Conan O'Brien, Steve Gustafson