I Was the Masturbating Bear on ‘Late Night with Conan O’Brien’

I couldn’t believe what I was looking at. It was January of 2009, and I was the clip research intern on Late Night with Conan O’Brien. Part of my duties included digging through old episodes to prepare for the final week of shows in February before O’Brien departed for The Tonight Show in Los Angeles. That’s when I found a clip from an early episode that featured an old recurring bit called “Actual Items,” where O’Brien would show newspaper fliers with obviously faked captions. In this particular rendition, he pointed to an image of a plush bear with an oddly positioned arm. The joke went something like, “Order now and get half off this masturbating bear.”

I was pretty sure this “Actual Items” predated the first appearance of the Masturbating Bear I knew best: the notorious Late Night character who would regularly appear on the show and pleasure himself with reckless abandon. But I wasn’t completely positive, so I decided to go directly to the source — Late Night writer Michael Gordon, or more aptly, the man in the Masturbating Bear suit.

Gordon had been with Late Night since the very beginning of Conan’s run, yet he told me that he didn’t remember this clip. He also told me that while he’d always played the Masturbating Bear, the character was created by writer Brian Reich (who recently passed in September). Gordon eventually concluded that this was, very likely, the first mention of the Masturbating Bear and that it was probably stored somewhere in Reich’s brain to be used again for the actual character later on. 

The Masturbating Bear was among the longest-running jokes on Late Night, and he continues to hold a special place in the hearts of Conan fans even years after his final appearance. As for Gordon, I recently sought him out once more to have him share his memories from the 20 years he spent as the character — from the time he ceded the role to Jim Carrey, to how Stephen Colbert literally brought him back to life, to the day Carrie Fisher saved him from a Han Solo-esque fate of being frozen in carbonite.

A Masturbating Bear Is Born

The Masturbating Bear was created by writer Brian Reich, who worked on Late Night from 1994 to 1999. Brian created the bear for a bit we used to do called “Pleasing the Affiliates,” where we made believe that NBC affiliates all over the country had problems with our show and we’d do different things to pander to them. Back in 1997, Brian made up a bit where one of our affiliates in Montgomery, Alabama was complaining about how so many of our characters were naked.

And so, we brought out this parade of characters like a giant ant and a giant skunk, and now they were all going to wear codpieces. The last one in the parade was the bear. In the script, Conan said, “And finally, our popular character, the Masturbating Bear, will not only wear a diaper, but he will be shackled.” Then I broke free of the shackles and started masturbating. The fun part was that we didn’t have a character named the Masturbating Bear, Brian just made that up. He created this universe where it was already a character, which it wasn’t.

I’d been chosen to play the bear because, before the Masturbating Bear, I was already playing bears on the show. My fellow writer Brian McCann used to do this bit where he was a loser — like “Loser on the Beach” and “Loser in a Hot Air Balloon” — and every time it ended with him being attacked by a bear. That was always me playing the bear; so I did it for this one, too. Who knew it would become this industry?

After the first appearance of the Masturbating Bear, NBC sent us a note saying, “Haha, very funny, but don’t do it again.” According to my notes, though, we did it again just two weeks later. And as the bear got established, we used him everywhere and in every bit. It was a very fun crutch.

The Masturbating Bear Gets His Groove On

In the early days of the Masturbating Bear, I always came out in shackles, and I had two handlers played by Brian Reich and Mike Sweeney, who would later become the head writer. In the bits, I’d always break free of the shackles and begin masturbating while the two handlers would zap me with cattle prods. The character is very identified with the music “Sabre Dance,”  but early on, there was no music. It was very quiet, and you just heard the cattle prods. 

The music finally came along in what is still my favorite Masturbating Bear appearance. Brian Reich wrote this bit where the Masturbating Bear was put into a money booth that had a million dollars in it, and he was going to split his winnings with a viewer at home. The guy at home was played by Brian McCann. It was around Christmastime, so he explained how he’d fallen on hard times and how he wasn’t sure if he’d be able to get his kids gifts for Christmas.

I got into the money booth, and “Saber Dance” began. As soon as the music started, I began masturbating in the money booth, and I didn’t get any money. Once it’s over, I got out of the booth, and McCann had this one line that he delivered perfectly: “That bear just masturbated away my kids’ Christmas.”

An Imposter Masturbating Bear

In 1999, I got a note saying, “Jim Carrey wants to come out as the Masturbating Bear,” and on the day of the show, I got a call saying, “Jim Carrey wants to meet with you.” I went down to his dressing room, and he wanted me to put on the suit first and teach him how to do it. He wanted to learn all the subtleties. He wanted no one to doubt for a second that it wasn’t me. Then he put on the suit and practiced while I gave him notes. He really cared. 

The Masturbating Bear Goes West

During our last week of shows for Late Night in New York, Conan announced that we were going to The Tonight Show at 11:30 and we couldn't bring the Masturbating Bear. He wasn’t fit for 11:30, so we were going to freeze him in carbonite so future generations could enjoy him. They did this fantastic effect where I was put into this cylinder, after which I began masturbating. When Conan pushed a button, smoke came up, and when it cleared, there was this beautiful full-size Masturbating Bear frozen in carbonite. But then, Carrie Fisher entered and said, “You can’t do this to the bear! People love the bear!” She pushed the same button as Conan, undid the freezing, and I ran away.

After that, there was a chase through New York — some handlers chased me through the sewer system. But I jumped into the water, and next thing you know, I’m on a boat with Carrie Fisher in New York Harbor and we’re toasting each other with champagne. 

I really did think we were going to leave the bear behind after that final time in New York, and he never did appear on The Tonight Show. But when Conan went to TBS, we did a show during the first week where we checked in on a lot of our old characters. The Masturbating Bear had gotten a job at a local TV station where they do the lottery numbers. The joke was that the lottery guy would reach into my diaper and pull the lottery ping-pong balls out of there.

I was on the TBS show a couple of other times, but my favorite was when we went back to New York for a week of shows and the writer Dan Cronin came up with a bit where the bear had stayed back out east. He’d given up show business and was now a businessman bear living in the suburbs. 

We shot this whole thing with me on a train platform in a business suit with a cup of coffee and a newspaper under my arm. Then Conan brought me out live and prodded me, saying, “It must be really, really hard for you not to revert back to your old ways.” Of course, I ripped off the business suit, but I couldn’t get the pants off. Conan had to help me get the pants off while also acting like he was surprised by the whole thing. It was really funny.

The Masturbating Bear’s Final Bow (Wank?)

The last time we did the Masturbating Bear was in 2014. Stephen Colbert had shown footage of an actual bear in a zoo that was masturbating, and he tweeted out something like, “Tune in tonight when I become the first late-night host to show a clip of a masturbating bear,” knowing full well what he was doing, of course. 

The next day, Conan brought it up on the show and said that what Stephen Colbert didn’t know was that the Masturbating Bear was dying. We then cut to me in a hospital bed, where I was in a coma. It seemed as though I was going to die at any second, but there was a TV monitor with Colbert’s footage on, which we kept cutting back and forth to. Finally, I got out of the coma and started masturbating. Basically, Stephen Colbert saved the Masturbating Bear.

I will give myself a little credit, though: I might be a terrible actor who can’t handle lines, but I think I was actually pretty good as the bear. I had good timing for him, and some people see him as a sweet character. If you just hear the name, it sounds disgusting, but if you actually see it, there’s a sweet innocence to the bear that I think I brought to it.