The 1990s was one of the best decades for film comedy. Multiplexes were filled with crowd-pleasing hits from then-rising stars like Jim Carrey and Adam Sandler. Directors like Danny Boyle and the Coen brothers had weirder, quirkier comedy gems to offer. The comedies of the ‘90s were filled with hilarious villains like Shooter McGavin and Bill Lumbergh.
Pixar’s groundbreaking animated masterpiece Toy Story introduced audiences to Sid Phillips. The Christmas comedy-turned-home invasion thriller Home Alone introduced audiences to the “Wet Bandits.” And Mike Myers’ satirical cocktail of James Bond and the Swinging Sixties, Austin Powers: International Man of Mystery, introduced audiences to Dr. Evil.
10 Benjamin Kane (Wayne’s World)
Mike Myers and Dana Carvey managed to navigate the tricky transition from SNL sketch to feature-length movie with Wayne’s World, one of the biggest comedy hits of the ‘90s. The movie is hilariously self-aware, but it follows a traditional three-act narrative arc with a traditional villain.
Rob Lowe smarms up his on-screen persona to a hysterical degree as Benjamin Kane, the sleazy TV producer from Chicago who takes on Wayne and Garth’s public-access show with an ulterior motive. According to Garth, “If Benjamin were an ice cream flavor, he’d be Pralines and D**k.”
9 Begbie (Trainspotting)
Danny Boyle’s Trainspotting goes to some very harrowing places, but its manic, idiosyncratic style is defined by its dark sense of humor. The movie’s pitch-black comedic sensibility is embodied by its psychotic villain, Begbie.
Robert Carlyle’s unforgettable turn reimagines the sadistic Mr. Blonde as a Scottish party animal. He beats people up for fun and throws a glass into a crowd at a bar just to liven up his night with violence.
8 Christof (The Truman Show)
The satirical premise of The Truman Show is so juicy that it’s spawned an entire psychological disorder. Jim Carrey plays the titular star of the biggest reality show in the world. He learns that he was raised by a media conglomerate and that his entire life has been a hit TV series.
Ed Harris grounds The Truman Show’s satire of the media as the disturbingly callous creator of the show, Christof, who adopted Truman and would rather kill him on TV than let him escape into the real world.
7 Sid Phillips (Toy Story)
Pixar made the first fully computer-animated feature film of all time with its groundbreaking hit Toy Story. But the technical breakthrough of Toy Story wasn’t enough to make it a blockbuster; it also needed a story and a cast of characters that audiences could really care about.
Woody and Buzz are a pair of bickering protagonists that audiences can fall in love with and their adversary Sid Phillips – the toys’ worst nightmare – is a classic antagonist that audiences can hate.
6 Harry & Marv (Home Alone)
On paper, the premise of Home Alone doesn’t sound like it’ll work at all. It’s a Christmas comedy about a little boy being abandoned by his family and having to fend off an attack by sadistic burglars who want to kill him.
But that’s a testament to the performances of Joe Pesci and Daniel Stern as the villainous “Wet Bandits” – not to mention their young co-star, Macaulay Culkin – who dial up the cartoonish elements just enough to make it work.
5 Chip Douglas (The Cable Guy)
Jim Carrey’s career hit its first bump in the road with the box office failure of The Cable Guy. At the time, Carrey was one of the biggest movie stars in the world. As the titular villain in The Cable Guy, Carrey challenged his affable on-screen image with a decidedly dark role.
While ‘90s audiences didn’t appreciate it, The Cable Guy has since been venerated as a cult classic. Carrey plays a cable TV installer who obsessively pursues a friendship with Matthew Broderick’s everyman in a comedic take on psychological thrillers about stalkers like Cape Fear and The Hand That Rocks the Cradle.
4 Shooter McGavin (Happy Gilmore)
Christopher McDonald smarms it up beautifully as pro golfer Shooter McGavin in Happy Gilmore. As a representative of the snooty golf world that Happy disrupts, McGavin makes for a hilariously hateable counterpoint to Adam Sandler’s lovable titular goofball.
The audience already roots for Happy because he’s motivated by saving his grandmother’s home, but playing against McGavin makes rooting for him even easier. McDonald leans into every setup: “I eat pieces of s**t like you for breakfast!” “You eat pieces of s**t for breakfast?”
3 Charlie Meadows / Karl “Madman” Mundt (Barton Fink)
Regular Coen brothers collaborator John Goodman was the perfect casting for the role of “Charlie Meadows” in Barton Fink. He’s introduced as a mild-mannered traveling salesman staying at the same hotel as Barton, but he turns out to be a serial killer named Karl “Madman” Mundt, whose M.O. is decapitation.
Goodman’s warmth and familiarity make the audience inherently trust him when he introduces himself as Charlie, so the big twist and his true personality as Mundt land as truly horrifying.
2 Bill Lumbergh (Office Space)
Mike Judge’s cult workplace comedy Office Space is the quintessential satire of corporate America. Just as Ron Livingston’s Peter Gibbons represents every bored office worker, Gary Cole’s Bill Lumbergh represents the bosses they work for.
Cole’s monotonous line deliveries and bald-faced smugness make Lumbergh a pitch-perfect embodiment of everything soul-crushing about mundane office work.
1 Dr. Evil (Austin Powers: International Man Of Mystery)
It’s rare that a movie’s hero and villain are played by the same actor. In the Austin Powers franchise, Mike Myers plays both Austin and his megalomaniacal arch-nemesis. Dr. Evil is a spot-on spoof of James Bond villains.
He dresses like Blofeld and strokes a white cat, but he sounds like Lorne Michaels. On top of the Michaels impression, which pairs surprisingly well with the satire of Bondian villainy, Myers nails the deadpan line deliveries: “Riiiiight…”
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