We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 movie comedies from 1990-2000. Don’t forget to check out other lists throughout Thought for Your Penny.
10. Dumb and Dumber (1994) 67% at Rotten Tomatoes
Harry Dunne and Lloyd Christmas mean well when they take a cross-country trip to return a briefcase to Mary Samsonite. Unfortunately, the briefcase was a ransom drop, and they’ve found themselves in a bad predicament. Dumb luck appears to be working in their favor, though.
Director: Peter Farrelly, Bobby Farrelly
Starring: Jim Carrey, Jeff Daniels, Lauren Holly
9. Austin Powers: International Man of Mystery (1997) 70% at Rotten Tomatoes
Austin Powers was a shagadellic secret agent in the 1960s who had himself cryogenically frozen to stop nemesis Dr. Evil in the future. Unfortunately, he wakes up in a different world, where he’s a fish out of water and must depend on agent Kensington (the daughter of his former flame) to get him through.
Director: Jay Roach
Starring: Mike Myers, Elizabeth Hurley, Seth Green
8. There’s Something About Mary (1998) 83% at Rotten Tomatoes
Mary is something special, and it leads to her attracting a slew of creepy men looking to be her beau. One of which is Ted, who missed a date with her in high school when he got his franks and beans stuck in a zipper. Now he’s competing with every creepy guy in Florida for her affections.
Director: Bobby Farrelly, Peter Farrelly
Starring: Ben Stiller, Cameron Diaz, Matt Dillon
7. Happy Gilmore (1996) 60% at Rotten Tomatoes
Happy Gilmore wants to be a hockey player, but the only things he’s good at are hitting a puck and a person. But golf coach Chubbs convinces him to play golf for the prize money to get his grandma’s house back. League champion Shooter McGavin has other plans though.
Director: Dennis Dugan
Starring: Adam Sandler, Julie Bowen, Carl Weathers
6. Half Baked (1998) 29% at Rotten Tomatoes
Three potheads are forced to sell pot to raise enough money to get their friend Kenny out of jail before he becomes some inmate’s fish. By doing it, they gain the attention of a rival drug dealer who’s not happy they’re cutting into his profits. They’ll figure it out somehow, but first – more weed.
Director: Tamra Davis
Starring: Dave Chappelle, Jim Brewer, Guillermo Diaz
5. Friday (1995) 74% at Rotten Tomatoes
Craig got fired on his day off, and now it’s Friday, so he’s chilling on the porch and smoking weed with his boy Smokey. That weed belongs to local drug dealer Big Worm, however, and he wants either his drugs or his money by tonight. On top of that, local bully Deebo is on the prowl, so it’s not going to be easy to raise that cash.
Director: F. Gary Gray
Starring: Ice Cube, Chris Tucker, Tommy “Tiny” Lister
4. Clerks (1994) 88% at Rotten Tomatoes
Dante is called into work on his day off, and now he and Randal are stuck hating their jobs and the crazy customers that come with it. On top of that, his ex Caitlin is getting married, his current girlfriend has sucked more dicks than you want to think about, and a man died in the bathroom.
Director: Kevin Smith
Starring: Brian O’Halloran, Jeff Anderson, Marilyn Ghigliotti
3. Orgazmo (1997) 48% at Rotten Tomatoes
Joe Young is a naive Mormon missionary who finds himself abandoning his mission to act as a porn superhero (with the help of a stunt cock). Armed with an Orgazmorater that can cause victims to have an orgasm, he ends up becoming a porn sensation that spawns many sequels. It’s not long before he becomes a real-life hero fighting evil villains.
Director: Trey Parker
Starring: Trey Parker, Dian Bachar, Robyn Lynne Raab
2. Groundhog Day (1993) 96% at Rotten Tomatoes
Phil is a disillusioned weatherman sent to Punxsutawney to film the groundhog appearing to predict the end of winter. The next day, he wakes up to find it’s still Groundhog Day. It consistently happens until he pushes through multiple suicides and finally becomes a better person.
Director: Harold Ramis
Starring: Bill Murray, Andie MacDowell, Chris Elliott
1. Bill & Ted’s Bogus Journey (1991) 54% at Rotten Tomatoes
Bill S. Preston, esq. and Ted Theodore Logan are destined to become the world’s saviors in the future. But first, they have to come back from the dead after android doubles from the future kill them. The afterlife has never been more hilarious than in this surprisingly poignant movie.
Director: Peter Hewitt
Starring: Keanu Reeves, Alex Winter, William Sadler