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The Big Lebowski (1998)
8.1/10on IMDb
Released
The decade's great comeback story. After Fargo, the Coen brothers' noir parody about a bowling slacker mistaken for a millionaire made just $17 million in the US against a $15 million budget, then went to video and became a phenomenon: the first Lebowski Fest was held in Louisville, Kentucky, in 2002, and the Library of Congress added it to the National Film Registry in 2014.
Jeff Bridges' Dude and John Goodman's Walter are one of the great comedy double acts. The plot barely matters; the dialogue, rugs and White Russians do.
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There's Something About Mary (1998)
7.1/10on IMDb
Released
The movie that made gross-out comedy a blockbuster: the Farrelly brothers' romantic farce made $369 million worldwide on a $23 million budget and was the fourth-highest-grossing movie of 1998. Ben Stiller's hapless Ted spends 13 years pining for Cameron Diaz's Mary, and every rival suitor is worse than the last.
The hair-gel scene is the famous one, but the movie's secret is that Diaz plays Mary as genuinely lovable, so the romance holds the chaos together. Matt Dillon's sleazy detective is a bonus.
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Rushmore (1998)
7.6/10on IMDb
Released
Wes Anderson's breakthrough, co-written with Owen Wilson: a precocious prep-school student who throws himself into every club and activity on campus starts a feud with a sad industrialist over a first-grade teacher. Jason Schwartzman is the oddball lead, but Bill Murray's quietly wrecked performance won him the Independent Spirit Award for Best Supporting Male.
It did only modest business in theaters, then became a cult favorite and joined the National Film Registry in 2016. It is the deadpan, bittersweet choice on this list, and the place to start if you have only seen Anderson's later, more ornate movies.
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Office Space (1999)
7.6/10on IMDb
Released
Mike Judge's revenge fantasy for everyone who has ever filed a TPS report. It flopped when it opened on February 19, 1999, with about $10.8 million in the US and $12.1 million worldwide on a budget of around $10 million, then got a second life on home video and through endless Comedy Central airings.
The cubicle details are what make it timeless: the passive-aggressive boss, the jammed printer, the mumbling coworker and his stapler. Anyone who works in an office will recognize every scene.
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Election (1999)
7.2/10on IMDb
Released
A pitch-black satire of a high school student council race, adapted by Alexander Payne and Jim Taylor from Tom Perrotta's novel. Reese Witherspoon's relentless overachiever Tracy Flick is one of the great comic characters of the decade, and Matthew Broderick, cast against his Ferris Bueller image, is the teacher who decides to stop her.
It earned an Academy Award nomination for Best Adapted Screenplay. Choose it when you want comedy that makes you wince as much as laugh, about ambition and petty grudges far beyond high school.
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American Pie (1999)
7.0/10on IMDb
Released
The teen sex comedy that closed the decade and revived the genre: four high school friends make a pact to lose their virginity before graduation. It is raunchy, and some of the humor has dated, but it has more heart than its reputation suggests, mostly thanks to Jason Biggs' total commitment to humiliation and Eugene Levy as the most supportive, mortifying dad in movies.
Seann William Scott's Stifler became the template for a decade of obnoxious best friends. Watch it with friends, not with your parents.
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Galaxy Quest (1999)
7.4/10on IMDb
Released
A loving parody of Star Trek and its fans: the washed-up cast of a canceled space show, led by Tim Allen and a gloriously miserable Alan Rickman, get abducted by aliens who think the old episodes were documentaries. Sigourney Weaver and Sam Rockwell are just as good.
It won the Hugo Award for Best Dramatic Presentation, and at a 2013 Star Trek convention in Las Vegas fans ranked it the seventh-best Star Trek movie, although it isn't one. It is the warmest comedy here, and an easy pick for sci-fi fans and families alike.
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