Rushmore (1998)
The best Wes Anderson film might be The Royal Tenenbaums (2001), but my favorite remains Rushmore. In addition to pitch-perfect production design, score, and performances, the film manages to tell a story about insanely awkward individuals without resorting to cringe comedy or mean-spirited antics. Max Fischer — brilliantly played by Jason Schwartzman — is a teen struggling to co-exist with those around him, and we feel for his awakening and efforts even as we laugh aloud at his antics. Bill Murray in the role of unfortunate mentor is equally sublime in its suggestion that age doesn’t make us wiser or better, it only makes us more tired. (Rob Hunter)
Election (1999)
In Election, Alexander Payne’s brilliant 1999 comedy, Reese Witherspoon stars in her greatest pre-Legally Blonde role as Tracy Flick, a major overachiever who is very, very set on being elected student body president at her high school. However, a certain teacher — played by none other than Matthew Broderick, who has left his Ferris Bueller days behind him and here takes a stab at an Ed Rooneyesque character– takes it upon himself to do whatever it takes to prevent the manipulative Tracy from succeeding. What follows is a hilarious and biting satire of American politics, all condensed into a tiny, inconsequential presidential election at a Nebraskan High School. (Madison Brek)
Galaxy Quest (1999)
What happens when a spoof of Star Trek ends up being one of the most memorable Star Trek movies of all-time? Enter Galaxy Quest and its eclectic and sensational cast. Featuring performances from Sigourney Weaver, Tony Shalhoub, the late Alan Rickman, and Tim Allen, the film follows a day in the life of a canceled sci-fi television series. During an appearance at a Comic Book convention, the cast of the TV show meets up to sign autographs for the fans. They end up meeting a bizarre fan that will take them on a journey to save the universe, not for a television audience but for real this time. What makes a great comedy is some memorable lines and Galaxy Quest has them in spades. Just remember that when things get tough, “Never Give Up. Never Surrender.” (Max Covill)
Office Space (1999)
“It’s not okay because if they take my stapler then I’ll set the building on fire.” Admittedly, the workplace culture featured in this 1999 cult classic now feels a little dated in places—although, to be fair, that’s also kind of funny in itself—but poking fun at the soul-crushing nature of workplace bureaucracy never gets old. From turning red staplers into hot ticket items to contributing to T. G. I. Friday’s removing their “flair” requirement, Mike Judge‘s hysterically funny skewering of office life has had real-world impact, and its message about the life-changing art of giving less of a fuck has aged like fine wine. Also, watching a bunch of people wreck one of the misanthropic demons known as printers is the next best thing to getting to smash a printer yourself. (Ciara Wardlow)
Wonder Boys (2000)
Michael Douglas‘ greatest performance can be found right here in this witty and warm adaptation of Michael Chabon‘s beloved novel from director Curtis Hanson. He plays an English professor juggling issues with women, career, and his ability to write another novel after the long ago success of his first. It’s a film you never want to see end, a movie you wish you could live inside of, as the characters, relationships, and interactions all share such an affection and joy (even when they’re berating each other). Douglas is joined by an equally strong and talented supporting cast in Tobey Maguire, Frances McDormand, Robert Downey Jr., Rip Torn, Jane Adams, Alan Tudyk, and Katie Holmes. (Rob Hunter)
Wet Hot American Summer (2001)
In 2001, David Wain made his directorial debut with a little film called Wet Hot American Summer. Set in the early ‘80s, the film takes place at a fictional summer camp and follows the wacky hi-jinx of the camp counselors. It’s a parody of sex comedies but done in the most absurd, over-the-top way imaginable. And it works so well because the ensemble cast, consisting of Paul Rudd, Janeane Garofalo, David Hyde Pierce, Molly Shannon, Amy Poehler, Bradley Cooper, and a whole lot more, are fully committed to the bit. Every scene is funnier than the next. Whether it’s Garofalo rattling off a long list of Jewish names or Rudd pouting after being forced to pick up his lunch tray, it’s nonstop hilarity. The capper though is Christopher Meloni as a mess hall cook that talks to a can of beans and humps a refrigerator. In short, WHAS is the funniest movie of all and it’s not even particularly close. (Chris Coffel)
Anchorman: The Legend of Ron Burgundy (2004)
It’s hard to imagine a world without the sarcastic yet literal Will Ferrell / Seth Rogen / Judd Apatow brand of absurd, referential, improvisational comedy. It’s been 15 years since Ron Burgundy introduced us to it in its full original form, and we haven’t looked back. I rarely go a day without crossing paths with an Anchorman: The Legend of Ron Burgundy reference. Whether it’s the “pattern on the pants” of a subway bystander, the “formidable scent” of Odeon’s infamous cologne Sex Panther (“made with bits of real panther, so you know it’s good”), San Diego’s nautical namesake, the proper definition of “diversity,” the wherewithal to keep my female friends away from bears during that time of the month, or an unfortunate realization that “milk was a bad choice,” the film is all around us. And that’s because it’s fucking hilarious. Nearly every single line, from start to finish, is a joke that lands with the power of a belly laugh. It defined a thriving era of comedy that will never be forgotten. (Luke Hicks)
Shaun of the Dead (2004)
As far as horror comedies go, the first entry to the Cornetto Trilogy has to be the king. Edgar Wright and Simon Pegg took their pop culture remix machine, honed to perfection on two seasons of Spaced, and aimed it straight for the brain of George A. Romero. Whereas Romero’s Dead movies critiqued race and consumerism in post-war America, Shaun gives us middle-aged Gen-X milieu set against the backdrop of suburban London. Featuring Wright’s trademark kinetic shooting style, star-making performances from Pegg and fellow Spaced alum Nick Frost, and the best use of a Queen song since Wayne’s World, Shaun of The Dead isn’t just the best horror comedy of all time, it’s one of the best comedies, period. (M.G. McIntyre)
Kiss Kiss Bang Bang (2005)
Writer/director Shane Black exploded onto the Hollywood scene with his lively takes on the buddy cop sub-genre, but this variation on the theme remains his crowning achievement. Part modern noir, part love letter to Los Angeles, and all hilarious. Robert Downey Jr. and Val Kilmer are absolutely at the top of their game here in a murder mystery turned love story that has utter fun with dialogue, narration, and fourth wall shenanigans. It’s a rare exception in how it’s in medias res benefits the film too as the structure and format pay off in laughs and surprises throughout. Add in Michelle Monaghan in a role that allows her to shine and you have a movie that never fails to entertain, delight, and amaze. (Rob Hunter)
