O’Doyle Still Rules: We Tracked Down the Bullies from ‘Billy Madison’

For the most part, this is just a throwaway joke for the adults watching the movie with their kids—the same as it was when a similar O’Doyle character was included in the 2006 Sandler movie Click—capitalizing on one of the most enduring images of the Sandlerverse, written before the Sandlerverse was even a thing. The O’Doyles were first featured in Billy Madison as a recurring line of oversized redhead brothers, all finding new ways to torment Billy, a manchild sent to repeat school one grade at a time in order to assume the throne of his father’s hotel empire.

But you probably already know this, because, if you’re an American between the ages of 20 and 50, you have almost certainly spent significant time watching Billy Madison. Naturally, I was one of those people, too, wearing out my VHS copy over the span of years, compelled by the mixture of a welcoming schoolyard tale with a frankly bizarre sense of humor that was sprinkled into almost every scene. (It’s hard to think of many studio comedies from this era that would’ve been able to get away with a completely random shot of a grown man casually spraying a hose on a kid sitting in the grass, while the kid says, “Who are you? I don’t even know you.”)

There were four O’Doyle brothers portrayed in the movie, each one a few years older than the last, and none of them ever acted much again. But at least for a time, they had to go through life etched into the collective consciousness as manifestations of obnoxious, absurd bullies—a walking catchphrase for callous aggression and overblown ego. So what happened to them this last quarter-century? Did they inadvertently inhabit any of the O’Doyle tendencies? Or did it backfire, setting off a tide of bullying against them?

Billy Madison was filmed in Ontario, Canada, a relatively cheap project made by a hesitant Universal Pictures, which was taking a gamble on a Saturday Night Live talent—right before that talent was about to be fired from the show—in his first starring role. Ramshackle production as it was, it turns out that at least several of the O’Doyles were more or less picked off the street, as they were happy to tell me after I hunted them down online, trying my absolute damndest to not creep them out with a cold message.

“A friend of mine contacted me—her little sister had heard a radio cattle call for tough-looking redheads,” said Colin Smith, 44, who played the 9th Grade O’Doyle (the one who pours what appears to be tapioca pudding on Sandler’s head in the cafeteria). “I was like, what the hell, let’s give this a shot. So I went down into Toronto, and as soon as I went in, I folded my arms over my chest to make myself tough-looking, and they were like, ‘Perfect! Do that! Hold that!’ And the next day they called me up and were like, ‘You got the part.’ I couldn’t believe it.”

Sean Lett, 48, who played the 12th Grade O’Doyle (the one who fills Billy’s locker with cow shit), has basically the same story. “My boss at the time was reading a paper that had a small want-ad for red-headed males, age 16–21, or something like that,” he told VICE, “and he pulled it out of the paper and said, ‘Hey, you should call this!’” Lett rang in and was invited to the casting call, where there were “red-headed dudes as far as the eye could see.” He got the part despite having never acted in his life.

The exception to this trend was Conor Devitt, 35, who played the 1st Grade O’Doyle, and has a bit more screen time than the three older brothers. (For the record, I wasn’t able to get a hold of Christian Matheson, the 3rd Grade O’Doyle, and thus don’t know his story; shine on you crazy diamond.) Devitt was only 10 in 1995, and was pursuing acting in earnest when his agent got him the audition. 

“Me and my dad showed up, and Veronica Vaughn—I forget her real name [Bridgette Wilson-Sampras]—was there,” he said. “My dad was fumbling all over himself. And then we did like a couple scenes that I don’t think made it into the film, but it was me and Adam, one on one. It was fucking crazy.”

The production they were joining wasn’t exactly a smooth one. Before filming began, the studio decided that Sandler and his co-writer Tim Herlihy needed some outside help, so producer Robert Simonds hired Rich Wilkes, who wrote the 1994 movie Airheads, to do an uncredited rewrite. (Simonds produced Airheads as well, in which Sandler plays a supporting role.) According to Wilkes, the deal was that Sandler and Herlihy had final say over anything that was changed.

“The assignment was to just straighten things out,” Wilkes said. “It wasn’t a question of story or dialogue or the movie being funny, it was all an issue of structure. Really basic shit, mostly. For instance, the draft they turned in had the margins set too wide. When I adjusted them, their script turned out to be almost 140 pages. That’s great for Boogie Nights, but not for a comedy. So one of my first jobs was cutting out 20–30 pages. Somewhere out there is a bonus half hour of their original screenplay which never got filmed.”

One issue that Wilkes found himself trying to straighten out was that the script felt too “episodic,” with characters appearing briefly in whatever grade Billy was in, never to be seen again. He suggested some characters that would stick with Billy, like his friend Ernie (the cool one who pees his pants). He also suggested the idea of a more dynamic bully: “Instead of having one little kid who chases him around with a slingshot the whole movie, make the threat evolve.” 

Wilkes said that the “O’Doyle rules” catchphrase itself was a Sandler/Herlihy addition, but that the characters came straight from him. “The name didn’t come from somebody who bullied me or anyone I knew,” he said. “I took the name from Brian Doyle-Murray, Bill Murray’s brother, because he’s one of the funniest guys ever. I added the ‘O’ because you want the O’Doyles to be instantly recognizable—that’s why they’re all redheads.”

With the script in somewhat constant flux, the filming itself got off on the wrong foot, too, when the initial director, Stephen Kessler, was fired three days into production, leading to Tamra Davis taking over with essentially no notice. “I flew up on Thursday and I was shooting on Monday,” Davis said. 

Production for the elder O’Doyles was pretty simple, for the most part: show up, say “O’Doyle rules,” raise your hands in the air. (There were a few other brief O’Doyle scenes shot, but they were cut from the final film.) Crucially, though, Devitt was on-hand for Billy Madison’s most infamous scene—the dodgeball massacre, in which Sandler is said to have thrown the ball so hard at little kids that he actually made them cry.

“Kids weren’t getting stretchered off or anything,” Devitt said. “But he definitely was making it look like a grown man chucking balls at kids.”

“[Sandler] kept saying that hurting kids equals comedy,” Davis said with a laugh. “That’s why it’s cut every time a kid gets hit—they’d get hit and just buckle, just on the ground like a battlefield, crying in a heap… I didn’t know whether to laugh or cry because it was so hard to see a little kid cry afterwards. But it was true, he really hit them with all his might.”

Upon release in February of 1995, critics tore the movie up. “Am I getting older, or do I have taste? I think I have taste,” Gene Siskel stupidly proclaimed on At the Movies. “He’s trying to be the King of the Peepee and Doodoo jokes. Worse, he isn’t,” Peter Rainer wrote in the L.A. Times. (Obligatory response: He called the shit “doodoo.”) But Billy Madison opened as the No. 1 movie in America anyway, making Sandler a bonafide movie star.

That also meant that the O’Doyle actors were suddenly minor celebrities in Canada. “It spread surprisingly quick,” Smith said. “I didn’t like the attention a lot at first, because it seemed almost negative. But it wasn’t—I just didn’t like how much attention I was getting. It was like, I had such a small role and all these people are recognizing me and talking to me, and I couldn’t understand how someone big would deal with this. They couldn’t go out.”

Devitt said the role followed him as he became a teenager. “People knew I was O’Doyle,” he said. “For most of my friends and inner circles through high school it was always embraced as being a positive, but there were one or two times when someone around the hometown would be like, ‘O’Doyle!’ and me and my buddies wouldn’t know them, and we’d be skateboarding or something, so there’d be a little confrontation. But nothing crazy, just boys being boys, people talking shit.”

Lately, the O’Doyle connection has started to fade a bit—and maybe some of that distance has proved to be a good thing for the group. “As time grew on, I’ve come to embrace it a lot more,” said Smith, who works at a brewery, and has a surprisingly elaborate cosplaying alternate persona, dubbed O’Doyle Rules Cosplay, of course. But some of the connection will never really go away.

“People know,” said Lett, who still works at the same performing arts center in Oakville where his boss told him about the casting call in the paper 26 years ago. “We had a plumber in at work at the theater and somebody said, ‘O’Doyle rules,’ and the plumber goes, ‘Ha, yeah, you kinda look like that guy.’”

The effects linger in other strange ways. Lett said his sister and nephew dressed up as the O’Doyles for Halloween a few years ago, and that the Houston-based pop-punk band O’Doyle Rules sent him some shirts and CDs at one point. (A recent O’Doyle Rules album title: Here’s a Nice Piece of Shit.) He also said that he became good friends with someone who was introduced to him because they, too, had acted in Billy Madison: Chris Mei, who—and I’m not making this up—was one of the dudes in the penguin costume. (Specifically, he seems to have been the penguin who made out with Chris Farley.)

Some nastiness does manage to sneak through every now and again, though, such as when TMZ recently included Devitt in a mean-spirited Where Are They Now roundup, posting a picture from his social media and describing him as looking “dodgy.” It felt like the type of senseless, cruel online bullying that serves as the new version of what Billy Madison was originally trying to teach a lesson against in the first place. But Devitt, who now works in commercial real estate, didn’t let it get to him—and has a more positive interpretation of their choice of words in the first place.

“I think they thought it was ‘dodgy’ because I threw the dodgeball,” he said. “That’s how I looked at it. Unless I looked sketchy then, but I don’t know what the guy’s prerogative was… TMZ, oh well, what can you say with them? I’m pretty confident and self aware of what I am and who I am, so I didn’t really put too much into it.”

Either way, the ongoing royalty checks don’t hurt—“I call it the Chinese food that Billy Madison bought,” Lett said—and being a part of cinematic history isn’t anything to scoff at, either. “I’m a part of arguably one of the best movies, kind of frozen in time there, so that’s cool,” Devitt said. “Looking back, it’s funny to think about.”

Rich Wilkes is still an active screenwriter (he recently wrote the Mötley Crüe biopic The Dirt), but he especially appreciates the ongoing magic of this weird-ass movie he worked on when he was starting out. “Having anyone remember anything that you worked on twenty-five years later is mind blowing,” he said. “Holy shit, I mean gifs and t-shirts and fan art ... popping up a couple decades later, especially for a movie that didn’t exactly destroy at the box office? That’s a badge of honor.”

Davis thinks the movie still works because of the way the studio ultimately let the zaniness fly in the final cut—like the decision to have a banana peel on the highway be the cause of the entire O’Doyle family’s death—allowing for a range of jokes that hit at different ages. “It was like, you either got it or you didn’t,” she said. “And as you watched it, you were probably wondering why people laughed at [certain things]. But then you turn 14 and now that’s funny. It plays with every age group.”

“There’s definitely a fondness in my heart for [Sandler],” said Smith. “But I’m not the first person in line [for his new movies]. I’ll get to it when I do.”

Lett, for his part, is even more measured about the movie that changed his life—and mine: “Really, if I had to choose between the two, I’d choose Happy Gilmore every time.”