The Devastating Paris Hilton Appearance from The Tonight Show with Conan O'Brien

HISTORY

I remember a segment of The Tonight Show with Conan O’Brien. Well, kinda. You know how they say that people won’t remember what you said or looked like, but they’ll remember how you made them feel? That’s what I remember.

I remember how this segment made me feel.

Confused, angry, awestruck, shocked, embarrassed, joyful. The emotions were a rollercoaster.

The segment? I’ll try to describe what I can. Conan had finished his monologue, I think. He was sitting behind the desk and talked about something to do with tradition at The Tonight Show. I don’t know.

Then he introduced Paris Hilton. She came out in a long, gold dress and had a golf club. I think she was supposed to be emulating Bob Hope? She proceeded to tell jokes. And these jokes land with a thud. I have never seen something fall so flat on television. I’ve seen a little fumbling. Especially with Conan. He seems to relish in the awkward.

This felt different. It was a bombing like I’d never experienced.

The crowd. Now in L.A., it was not interested in the oddity of Paris telling jokes. I remember thinking that L.A. was not a great place for comedy. I’ve never been, but it felt very different from the New York crowds that Conan and David Letterman entertained. Maybe it was a poor match up. Conan, like David, played with celebrity and weirdness.

Los Angeles didn’t seem open to it.

And, again, these are memories of it. I have thought about this off and on since it aired. I’ve also searched for it every few years. Never seeing anyone mentioning it. I wondered if I was the only one struck by it. I was probably remembering it wrong.

I can’t explain why this has stuck with me. Maybe for the absurdity or the memory of absurdity. Maybe because I was still in the wake of the recession. I had finished grad school the year prior. I studied library science as it was reported that there would be a flood of retirements in the coming years.

That didn’t happen. Everyone held on to their jobs as long as they could, funding was cut, and no one was hiring. I was substitute teaching and working on self-publishing comics in the spare room of my best friend’s condo. And Conan was on the move.

Like me, his life was in transition.

This past week I looked again. Better luck. I found the first image of it on Pinterest. I hadn’t dreamt this. I wasn’t insane.

I was wrong about the color of the dress. It wasn’t gold. It was a soft pink. Of course it was. It’s Paris Hilton after all. Was I wrong about the rest of it?

Then somewhere on the second or third page of a Google search I found a link to a Getty Image. It gave me more details: THE TONIGHT SHOW WITH CONAN OÕBRIEN -- Episode 10 -- Air Date 06/12/2009 -- Pictured: (l-r) Conan O'Brien, Paris Hilton during an interview on June 12, 2009.

I took notes and walked away for a week. I sat down to start writing this over the weekend.

Once I started, I decided to do more research, I found a link to an archive.org collection via r/conan. The episode is there. All episodes are if you’re interested. I just wanted to see one part of that 10th episode.

I started to watch it but paused after Conan walks out for his monologue. I wanted to write my memories of it as best I could before seeing it.

I just want to know if it was as weird as I remember.

WATCHED

Holy fuck.

That was as dreadful as I remember, but also a lot shorter. I thought it had gone on for much, much longer. From the time O’Brien started the segment intro to Paris walking back behind the current, it was only a minute and fifty-three seconds. She told three jokes.

I thought it was between five and seven jokes. The weirdness of it must have stretched it out in my mind.

It was great though. I could not stop laughing. I remember laughing hard at it and also having that pit in my stomach at the silence then. It was all there now.

Conan did talk about the old Tonight Show and Bob Hope coming out unexpectedly, delivering a few zingers then leaving. He wished aloud that there was someone of that caliber who could “stop by any time and class up the place”. Cue music. Out comes Paris.

It feels like she’s a little late on the entrance. The audience seems pleased though. However, I’d heard bigger applause in the monologue.

But the audience is quickly lost after the first joke. Very much a Bob Hope joke. A quick deprecating jab at herself. “Man, the last time I showed this much leg, I was getting a lot more than scale.” Her delivery was good.

(I’ve come to appreciate Paris as an entertainer in the style of Andy Kaufman.)

Conan sat at the desk watching and then waiting for something. Max Weinberg hit the drums, and a weak, single “woo” came from the crowd.

Joke 2: “I just did a USO tour, and trust me, I found plenty of weapons of mass destruction.”

Max hits a drumroll. Light applause, but it could have been coming from the crew to be honest. Conan nods his head, turns away from Paris, and looks to, I’m assuming, his producer or director.

Final Joke: “How ‘bout that. Well, I have to go. There’s a grand opening for the Paris Hilton ride at Universal. You have to be this big to get in.” Paris holds up the handle of her golf club.

Some shouts from the crowd. Conan applauds and thanks Paris. She leaves. Then Conan O’Brien does something I don’t think I’ve ever seen him do. He just sits there and grins.

It’s shocking. Normally he would have some quip or comment on it. He did in the monologue. It happens. Jokes sometimes flop, and the host will say something. It’s part of a talk show.

I’ve seen Conan laugh at how badly a sketch or joke was going on his show. This time nothing.

He turned off camera a couple times and nodded his head. I believe it was to Andy Richter now.

The crowd shouts and applauds. O’Brien waves it off and quickly moves to the next segment. No commentary on what just happened.

Watching this now, Paris seemed rushed off. I think there were more jokes or something else that was supposed to happen. But after two jokes that fell absolutely flat? Yeah, that’s a good reason to move on.

I also get what they were trying to do. It was L.A. Paris was still a hot ticket then. She had gone through her sex tape release, reality stardom, album, and a couple of movies. She was popular but also controversial.

Placing her at the level of Bob Hope and telling some double entendre jokes was funny. Juxtapose her classy dress, tradition of the tonight show, Conan’s sense of humor, her past.

It was absurd. It was weird. It poked fun at celebrity. It was everything that Conan O’Brien and his team did well.

It just didn’t hit, and I still think it’s mostly the crowd. It was just different. The monologue was up and down. Conan was already having a rough time with them. There were laughs but nothing huge. It was always split within the crowd.

One of the larger reactions was a joke about The Hills stars Heidi Montag and Spencer Pratt. That actually got boos and laughter. It was clear that reality TV was a dividing topic in L.A. at that time.

Paris, I guess, was loved but within only certain contexts in L.A.

WHY

I’m still not 100% sure why I was thinking about this clip for the past 15 years.

If I was forced to give an answer, I would tell you a grand theory about the dividing point between celestial and digital entertainment. That night happened to be when stations switched over to digital signals. The last day of analog television.

And while Conan’s work was built on the legacy of Carson, Letterman, and, yes, even Leno, he showed us that network tv was aging. His ideas of comedy were still cutting edge and weird. Comedy that could be awkward, odd, and a little dangerous.

It wasn’t just about celestial analog switching to digital. It was about the changing landscape of entertainment, streaming, and television as a whole.

The Tonight Show, and NBC, was always ready for primetime. Conan wasn’t. He knew late night should be where weirdos went to find entertainment. Network tv didn’t understand that.

Conan would move on from the show thanks to some backroom shenanigans that I won’t cover here. While his departure was less than ideal, he would find support online via Facebook and Twitter through his fans. They called themselves Team Coco.

He followed up The Tonight Show with a delightful documentary, Conan O'Brien Can't Stop, and successful eleven years of his talk show, Conan, on TBS.

Currently, Conan O’Brien hosts a podcast called Conan O'Brien Needs a Friend, as well as, Conan O'Brien Must Go, a travel show on Max (formerly HBOMax). He is doing well in this media landscape where much of the humor is built on his legacy.

While not the greatest hit for O’Brien’s run at The Tonight Show, Paris Hilton telling Hope-esque jokes certainly became the most memorable for me and funniest. I’m glad I was able to rediscover it.

It will stay with me as a reminder of changing times and the importance of an audience. And how legacy and tradition aren’t always the best fit. No matter how inspiring.

But it will stay with me, mostly, because I just love that shit.

Did you remember this segment? Or was I the only one. You can watch it on Archive.org. The Paris Hilton segment starts at 14:41.