CocoMania: Conan O’Brien’s Best Wrestling Moments

As a comedian that exists in the realm of the absurd, I have had two tentpole influences from my early youth (for better or worse): Conan and professional wrestling. What do they have in common? Well, both have featured celebrity guests, hyper-specific characters, a surprising number of hand puppets, people behaving like children, and wild tonal oscillations.

This past week, Conan O’Brien ended a late night talk show run that began way back in 1993, the same year that Monday Night Raw debuted. And while the show with a revolving cast has grown stale over the decades, Conan’s final string of episodes still felt fresh and youthful. Much has been said over the past week about Conan’s influence and immense talent, but revisiting numerous clips of wrestlers on the show’s nearly 28-year run inspired not just an article, but a listicle.

There’s a secret formula to a successful talk show interview with a wrestler. Regis knew it, Arsenio knew it, and despite not being a wrestling fan himself, Conan also made his own version of this formula. It involves playing the straight man to possible anarchy, be it violent or, in most cases just weird. He’s been a host to countless wrestlers over the years, including The Rock, Paige, Mick Foley, John Cena, Kurt Angle, Triple H, The Miz, a pre-WWE Great Khali, and a mid-WWE Great Khali with Cody Rhodes, Ted DiBiase & Big Show on the telenovela, Conando.

Some of these don’t age terribly well, whether it’s because a little person is used as a punchline, or the wrestler featured in the clip was, say, alleged to be a pimp or a murderer. But all of them make for fascinating viewing. Here are some of the best moments on Conan’s talk shows:

Chyna – January 2001

Chyna, the most underrated wrestler of all time, is game for more than just an interview in this clip from Late Night with Conan O’Brien. With Conan eager to attract high ratings for November Sweeps, he reveals Chyna is going to marry her longtime boyfriend in the next segment. However, instead of an appearance by THE GAME, we get the return of Joe Fatale’s silent, head-bobbing Little Jay Leno and a shocking, Graduate-inspired twist at the end.

The Big Show – January 2003

The jovial giant Paul Wight, née Big Show, made numerous appearances over the years on Conan, but his most famous one isn’t even his interview. In a clip used in many “best of” compilations, Conan is interviewing the colorful 73-year old sex educator Sue Johanson, whose frankness creates an unlikely comedy duo out of the previous two guests, Wight and Tom Selleck. She practically tees them up when she growls the words, “HUMONGOUS PENIS,” and the demonstration of “The Accommodator” is an all-time comedy classic.

Brian Stack, a current Late Show with Stephen Colbert writer, was also a Late Night writer known for beloved characters like “Artie Kendall, the Ghost Crooner” and The Interruptor. (He’s also entertainment’s funniest and kindest man, ask anyone.) He had some memories of an early appearance on the show:

I remember we did a few bits with wrestlers over the years. The one I recall most clearly is a fake cable channel called “Wrestler Babysitter Channel” that featured [Paul Wight]. He played a big, scary wrestler babysitting little kids. He was so enormous and intimidating looking but super nice and easy to work with. I remember him saying he’d just become a father himself and he seemed very emotional about it. Very sweet guy. My fellow writer Tommy Blacha, who worked with me on that, has always been a huge wrestling fan and actually wrote for pro wrestling for a while.

Jimmy Snuka, Captain Lou Albano, Sunny, and More – October 1996

Conan’s sidekick, Andy Richter is a wrestling fan. He’s appeared alongside a table of legends at the prestigious 2000 Miss Royal Rumble pageant, sadly marred by Mae Young’s unprofessional disrobing. He’s appeared as a guest commentator for Lucha Va Voom in LA. And he’s been rumored to be an early subscriber to the Wrestling Observer Newsletter back in the day.

Richter does a rare remote at the Cauliflower Alley Club, the Friar’s of wrestling, at a New Jersey Holiday Inn. Under the guise of election coverage, it becomes apparent that Richter may have used the shoot as an opportunity to just go to a fun thing, as the editors include a cute moment where Andy asks AOL-peak Sunny to say hi to his then-wife Sarah Thyre (of Strangers With Candy fame). But the real thrill is watching Jimmy Snuka talk for what feels like five minutes without making a lick of sense. The segment ends with wrestling’s all-time carny Capt. Lou shouting at no one in particular.

This would not be Yukon Jack’s only appearance. Brain Stack added, “Tommy [Blacha] also used Yukon Jack in another fake channel, ‘The Clothesline Channel’ where Jack clotheslined people in everyday situations.”

Sheamus – December 2012

Sheamus, who comes off a million more times likeable in his many appearances on the show than in wrestling, is often positioned as a multiverse version of Conan. He’s a fellow pale, irish ginger who happens to also be a jacked, 6’3, 270-pound monster. It’s a match made in heaven.

“Stone Cold” Steve Austin – August 1999

There’s nothing particularly special about this segment. It’s just peak Steve Austin teaching Conan and Andy how to drink beer like him. When Conan figures out he will get covered in beer in this segment anyway, he dips his tie into his Natty Light and suckles away.

Vince McMahon – June 1999

Vince McMahon has two modes when he appears on late night talk shows. There’s “The Letterman” which sees Vince unusually square and awkward, leading to a dull interview. Then there’s “The Costas” where Vince leans in and screams at the host an inch from his face. For better or worse, this is the former, but it’s still fun to see Conan poke fun at McMahon, who has seemingly never been comfortable around someone cooler than him.

The Fabulous Moolah & Mae Young – March 1995

While promoting the 50’s women’s wrestling documentary, Lipstick & Dynamite, the octogenarian duo of shoot pimp The Fabulous Moolah and kayfabe(?) hornball Mae Young appeared on Conan. These two developed a very bizarre but delightful rapport on television late in life, with Moolah half-heartedly trying to control Mae’s humping, thrusting, party girl antics. Like the aforementioned Miss Royal Rumble moment, it all became about Mae Young’s breasts again. When Conan asks a question about padding, Mae pulls out a nippled bra pad and smears it on the face. The prolonged reaction from the audience for every bizarre step of the way ranks this moment high.

Yokozuna & Mr. Fuji – November 1993

Conan’s very first wrestling interview from November ‘93 is also one of the best. Manager Mr. Fuji’s “devious” persona rightfully feels like a relic from a bygone era, which makes him the perfect foil for an interview with the often anachronistic Conan. WWF Champion Yokozuna impressively keeps a straight face (respect) through the entire segment, even during one of the jarring mid-show bits early Conan would quickly abandon involving a spinning boy named Dizzy. But the real treat is when Conan dissects Mr. Fuji’s reverence to Yoko, causing him to break character.

Cassandro – March 2017

Cassandro, the truly magnificent Liberace of Lucha Libre, is in a unique position in this remote segment from Conan’s Mexico special. Typically drawing attention with ageless athleticism, exotico theatricality and glamorous outfits, the gay wrestling icon honestly pales in comparison to Conan’s “El Gallo Loco,” an incessantly crowing rooster luchador. Andy Richter then tops it with a lucha gimmick that I need to see executed for real. (You have the time now, Andy!)

Goldust & Marlena – March 1996

Sure, a lot of the early Goldust character was mired in regrettable gay panic shock value, but there’s also so much more going on that this still ranks high on the list. Clearly, a wrestling fan helped produce this segment, which gives a 100% kayfabe Goldust & Marlena the full WWF-style entrance complete with music, robe and um, gold dust. The character work here cannot be [sucks air in] penetrated, as the typically unflappable Conan seems genuinely uncomfortable at points. Marlena takes director reins so Goldust can get an extreme close-up at one point, while the knowing Andy smirks from a distance as Goldust disrobes and crawls under the desk.

Honorable Mention: DANHAUSEN

A longtime fan of Conan’s, Danhausen recently made an appearance on the “Conan Needs A Fan” podcast. Danhausen has described his character as “Conan O’Brien got possessed by a demon” and anybody put off by Danhausen’s German expressionist-faced, jar-of-teeth-wielding character, very committed, very evil character needs to see this genuinely sweet interaction between the two. Let’s hope Conan uses some of his free time to reunite with his longtime fanhausen, perhaps using some of his Cassandro-trained lucha libre and Goldust-learned erotic mind games.