Stealing Boggle Trophies: When Celebrities Take on the Villain Cameo

Search the internet and you’ll find plenty of examples of funny celebrity cameos or celebrities who make self-deprecating jokes about being bad guys, but our society has yet to satisfactorily catalog the far less common trend of celebrities who have made a cameo on TV as themselves and acted as the bad guy. That’s a clunky way to describe it, but it is an under-recognized way for a celebrity to seem like they’re cool and “in on the joke” without it necessarily coming across like an obvious “look how cool and in-on-the-joke I am” PR move (like, for example, James Franco sidestepping the perception of him as a creepy weirdo by playing himself as a creepy weirdo on 30 Rock).

There’s also a distinction to be made between this and when a celebrity guest star turns out to be a bad guy, like when Stanley Tucci almost shot a man on Monk. Tucci wasn’t playing himself, he was playing an unhinged Method actor who got so obsessed with Adrian Monk that he thought he was getting revenge for the murder of Monk’s wife. That’s different from when Randy Travis appeared on King Of The Hill, where he played himself and ripped off a song Peggy Hill wrote, turning her friends and even some of her family against her. Randy Travis is a bad guy in the world of that show.

Of course, “bad” is relative, but it should generally go at least a step beyond “mean” or “vulgar.” Murderers are bad, liars are bad, and bullies are bad. Kate Winslet on Extras, for example, with her penchant for being surprisingly filthy and her craven desire for an Oscar, is not bad. When Patrick Stewart guest-starred on the same British comedy, he played against type while pitching a movie where he can undress women with his mind and then ride his bike on the grass while they’re distracted. That was off-putting, but not evil.

So, in honor of Randy Travis and the stolen song (which includes a line that only Peggy could’ve written, referring to her skills at a certain word-search game) we’ve dubbed these “Boggle Trophies,” or the most devious cameos by celebrity guest stars. By design, this is not an exhaustive list. Rather, the idea is to help illustrate this kind of cameo and make it easier to spot Boggle Trophies in the future.

Randy Travis in King Of The Hill

When the Hill family and a group from their church go to a country music festival in “Peggy’s Fan Fair,” Peggy is shocked to hear Randy Travis debut a new song that sounds remarkably similar to one that she had previously written and sent to him. Nobody believes her, despite the song’s opening lines (“I have a Boggle trophy, on my bedroom shelf”) being a reference to Peggy’s oft-mentioned Boggle acumen, and she punches Travis in the face when he denies stealing her lyrics. Later, when playing the song live, he even rips off a story that Peggy told him about growing up in Montana and being bullied for having big feet. After Peggy accidentally knocks Travis’ trailer into a lake and Hank runs in to save him, Travis tells everyone that he was the one who saved Hank — and that’s it. He never learns a lesson or gets redeemed, he’s just a jerk.

Adam Sandler in Brooklyn Nine-Nine

In “Operation: Broken Feather,” Andy Samberg’s Detective Jake Peralta gets his own Frank Grimes (the Simpsons meta-antagonist who dared to call out Homer’s habit of lazily stumbling into good fortune) in the form of Adam Sandler, as himself, who gives Jake a hard time while he’s looking for a suspect. Sandler, who phones-in the performance in a way that seems like he’s just as annoyed at Samberg for calling in a favor as his “character” is at Jake Peralta (but in a funny way), casually rips Brooklyn’s wackiest cop apart and essentially brings down the show’s whole “cops but funny” premise by reacting to Jake’s shenanigans the way a real person would (or at least the way the Sandman would).

Neil Gaiman in The Simpsons

Ron Howard is famously mean to Homer whenever he appears on The Simpsons, but he’s not quite as bad as one-time guest star Neil Gaiman, who joined Homer’s Ocean’s 11-style heist crew as they tried to get rich writing a soulless YA knock-off of Twilight and Harry Potter. The joke, initially, is that Gaiman is an accomplished writer all on his own, but Homer and his crew of ghostwriters (including Bart, Principal Skinner, Moe, Patty, and Professor Frink) only let him join because he’s pathetically desperate to have friends. In the end, though, Gaiman gets the final twist in the heist by stealing the book and publishing it under his own name. He even poisons Moe, his co-conspirator, to cover up the fact that he’s illiterate and stole all of his books from other writers.

Wayne Brady in Chappelle's Show

Traditional self-deprecating cameos tend to be more of a PR play than the far more artistically fruitful — yet under-appreciated — Boggle Trophy cameo, but that’s sort of the explicit vibe of Wayne Brady’s cameo on Chappelle’s Show. Incensed by a gag from an earlier episode, in which comedian Paul Mooney quipped that “white people like Wayne Brady because he makes Bryant Gumbel look like Malcolm X,” Brady forces Dave Chappelle to join him on a violent night of drug-dealing and rampaging, showing him the real Wayne Brady (one who occasionally feels the need to “choke a bitch”) in the process. Though it was obviously the intention, it did successfully make Brady seem a little more hip.

Jon Voight, Raquel Welch, and Bette Midler in Seinfeld

The Seinfeld finale forced viewers to reckon with the idea that the show’s central foursome were toxic to themselves and everyone around them, but it’s not like the gang was treated well by any of their celebrity guest stars. Jon Voight immediately bit Kramer in the arm when the hipster doofus tried to ask him if he ever owned a Chrysler LeBaron (though Kramer did acknowledge that the attack was justified). Raquel Welch terrorized Broadway producers, beat up Kramer and broke his Tony award, then attacked Elaine (catfight, mrrow) when she thought she was making fun of her signature stiff-armed dancing. And Bette Midler crowded the plate when she played catcher in a charity softball game, fully justifying George’s decision to barrel into her even though it jeopardized her role in Rochelle, Rochelle: The Musical. Boggle Trophies for all three of them.

Mark Cuban in American Dad!

In “Introducing The Naughty Stewardesses,” Stan and Francine Smith take a vacation and meet up with the eponymous team of flight attendants, who are basically a spoof of Charlie’s Angels and fight crime for some reason. And it’s a good thing the Naughty Stewardesses are around, because billionaire Mark Cuban’s bodyguard tries to take an oversized carry-on onto their plane that contains his boss’s plans to blow up the sun. The Naughty Stewardesses sneak into Mark Cuban’s mansion and confront him, at which point he reveals that he’s trying to “blow up” the Phoenix Suns NBA franchise. Not as evil, but still a little evil, especially since the Naughty Stewardesses’ airline is an official sponsor of The Suns!

Jessica Biel in BoJack Horseman

Jessica Biel doesn’t earn her Boggle Trophy until later in her multiple appearances on BoJack Horseman, where she plays one of Mr. Peanutbutter’s exes. Introduced as a self-obsessed parody of herself who constantly criticizes Mr. Peanutbutter’s refusal to ever reject any acting roles that come his way, even when they’re awful (while she brags about her great work in the movie Stealth), she pretty quickly descends into full-on madness after an earthquake traps her and a bunch of guests at an event for Mr. Peanutbutter’s gubernatorial campaign underground in Season 4. By day seven she has killed Zach Braff and declared that fire is the only law, and by day eight she has crucified Mr. Peanutbutter and started trying to burn him to death.

Sam Barsanti has written about pop culture for 10 years. He canonically exists in the Arrowverse.