25 Super Comedies of the Last 20 Years

Not talking the hipster stuff, or the ironic stuff, or the postmodern stuff. I am talking FUNNY. FUNNY! Listed in chronological order, some of these films have truly changed the face of comedy over the last two decades, while others just make you laugh until it hurts...so good.
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1.
L.A. Story (1991)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
With the help of a talking freeway billboard, a wacky weatherman tries to win the heart of an English newspaper reporter, who is struggling to make sense of the strange world of early 1990s Los Angeles. (95 mins.)
Director: Mick Jackson
“ If you've never been to Los Angeles, this film is still funny, but if you have ever lived in LA, it is riotously hilarious. Casual earthquakes, bouncy twenty-somethings with too many vowels in their names, agent jokes - and the quintessential quote: "Let's just say I was deeply unhappy, but I didn't know it because I was so happy all the time." It's lines like that that make one realize LA is a state of mind. ” - Sara NK
 
2.
Wayne's World (1992)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Two slacker friends try to promote their public-access cable show. (94 mins.)
“ Goofy and hilarious, and the reason a whole new generation knows the words to Bohemian Rhapsody and Foxy Lady...but! Having watched again recently, I realized WW is also 50% of today's pop culture DNA. Every other line has become common banter in middle schools and at dinner parties alike, to the point where watching it now, everything feels recycled - when really, this 1992 film is the origin of most of the humor for Generation X/Y/Whatever. Seriously. Go watch. It is crazy. ” - Sara NK
 
3.
My Cousin Vinny (1992)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Two New Yorkers are accused of murder in rural Alabama while on their way back to college, and one of their cousins--an inexperienced, loudmouth lawyer not accustomed to Southern rules and manners--comes in to defend them. (120 mins.)
Director: Jonathan Lynn
“ Who knew Pesci was a comedian? Or that courtrooms could be hilarious? Every scene with the Oscar-winning/deserving Marisa Tomei is amazing and quotable, and a delight to behold, again and again...Mona Lisa Vito 4-evuh. (And those outfits were supposed to be ridiculous, but I think they might be in Lady Gaga's closet this very minute. Talk about cultural impact.) ” - Sara NK
 
4.
Army of Darkness (1992)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A man is accidentally transported to 1300 A.D., where he must battle an army of the dead and retrieve the Necronomicon so he can return home. (81 mins.)
Director: Sam Raimi
“ Multiple boyfriends have made me watch this with them numerous times, so I know what I mean when I say: is FUNNY. Bruce Campbell should be a ginormous star, but instead, somehow, he just gets to do commercials and think about when he had a couple cult hits. It makes one wonder if Hollywood might not know what the hell it's doing. ” - Sara NK
 
5.
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A weatherman finds himself inexplicably living the same day over and over again. (101 mins.)
Director: Harold Ramis
“ To me, Andie MacDowell is as interesting as cardboard, but it seems Bill Murray is the perfect antidote. This nutty film is a classic, and ranks with the top comedies when it comes to cultural saturation. I'd bet most Americans over the age of 20 (and under 55?) can't hear "I Got You, Babe" without flashing immediately to that torturous B&B clock radio. Which is too bad, maybe, for Sonny & Cher purists, but you don't hear the Punxsutawney Chamber of Commerce complaining. ” - Sara NK
 
6.
So I Married an Axe Murderer (1993)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A San Francisco poet who fears commitment suspects his girlfriend may not be who she appears. (93 mins.)
Director: Thomas Schlamme
“ One of those movies that should not be as funny as it is. That title alone should have deemed it straight-to-DVD, but I guess distributors were more tolerant in the early 90s. Somewhere between the beat poetry ("woooman, whoooa-man") and the Scottish family ("HEAD! MOVE!"), this one takes its place among the last 20 years' funniest. ” - Sara NK
 
7.
Bullets Over Broadway (1994)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
In New York in 1928, a struggling playwright is forced to cast a mobster's talentless girlfriend in his latest drama in order to get it produced. (98 mins.)
Director: Woody Allen
“ Woody Allen's funniest movie since "Sleeper." Okay, since "Annie Hall." Fine, since "Broadway Danny Rose." Whatever, the point is, this film is screwballistic and bantertastic. Dianne Wiest and Jennifer Tilly are to die for, and John Cusack and Chazz Palminteri aren't so bad themselves. If you like gangsters, or Broadway, or the 1920's, or laughing, this one's for you. ” - Sara NK
 
8.
Clueless (1995)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A rich high school student tries to boost a new pupil's popularity, but reckons without affairs of the heart getting in the way. (97 mins.)
Director: Amy Heckerling
“ This Jane Austen modernization is even better than the original, and I'd bet a modern Jane would agree. Bubble-headed blonds and young fashionistas sashé through Beverly Hills and even (gasp) The Valley as we gobble up their dorky suaveness and thank heaven we're no longer in high school. Delicious/brilliant/hilarious film in a total, like, poppy/tweeny disguise. ” - Sara NK
 
9.
Swingers (1996)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Wannabe actors become regulars in the stylish neo-lounge scene; Trent teaches his friend Mike the unwritten rules of the scene. (96 mins.)
Director: Doug Liman
“ Written by Jon Favreau, with breakout roles for Favreau and Vince Vaughn. (Or, the first time VV got to play himself and then kept going.) If you've ever been called "money" or can't have even a layover in Nevada without hearing multiple "Vegas, Baby!"s, this film is why. The ultimate indie buddy pic, it is a great, earnest story about guys in their 20's and how they handle love, loss, hope, and friendship. ” - Sara NK
 
10.
Flirting with Disaster (1996)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A young man, his wife, and his incompetent case worker travel across country to find his birth parents. (92 mins.)
“ At first viewing, this film may seem meandering and abrasive. If so, give it another shot when you are feeling less uptight. It is...hilarious. Armpit love, gay cops, white Ford Tauruses, an amazing cast, and JERRY GARCIA, BLAH BLAH BLAH make for a delightful romp. Everyone brings it, from Mary Tyler Moore to Lily Tomlin, and I am almost glad FWD doesn't get the acclaim it deserves, because when I meet someone who HAS seen it, I know we are bonded at a deeper level. ” - Sara NK
 
11.
Romy and Michele's High School Reunion (1997)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Two dim-witted, inseparable friends hit the road for their ten-year high school reunion and concoct an elaborate lie about their lives in order to impress their classmates. (92 mins.)
Director: David Mirkin
“ Yay, female buddy comedy! Buddette comedy? Anyway, it may be easy to make fun of high school reunions, not to mention insecure 20-somethings, but this films nails it. Mira Sorvino and Lisa Kudrow are amazing, and even with characters that have only a few brain cells, their hearts and humor are enough to win you over and then some. Janeane Garofolo rounds it all out as the sardonic mean girl. ” - Sara NK
 
12.
The Big Lebowski (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it. (117 mins.)
Director: Joel Coen
“ I have only seen this movie twice, so I don't have a heart attack when I talk about it like most people do (I save my heart attacks for "Raising Arizona")...but even those two teeny viewings made me a big believer. Mishaps beget mishaps, drugs beget bowling, the Dude abides, etc. A Coen classic, and a plain ol' classic. "That rug really tied the room together." ” - Sara NK
 
13.
Office Space (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three company workers who hate their jobs decide to rebel against their greedy boss. (89 mins.)
Director: Mike Judge
“ A brilliant and unintentional precursor to even the British version of "The Office," this film makes working in an office bearable to this day. The reports, the coffee cups, the fax machines, the cubicles, the birthday cakes - all of it just feels more universal and more chuckle-worthy with "Office Space" moments running through one's head. ” - Sara NK
 
14.
American Pie (1999)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Four teenage boys enter a pact to lose their virginity by prom night. (95 mins.)
Director: Paul Weitz
“ I saw this movie grudgingly because a friend loved "Willow from Buffy," but I ended up laughing a helluva lot. Then it ended up saturating pop culture...intimacy with pies, Shannon Elizabeth, webcams, MILFs, and band camps all owe a debt of gratitude to this Prom-centric ensemble comedy. ” - Sara NK
 
15.
Dick (1999)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
Two girls wander away from a White House tour and meet President Nixon. (94 mins.)
Director: Andrew Fleming
“ Cute and funny revisionist American history? I'm in. Michelle Williams and Kirsten Dunst really do pull off this nutty look at Richard Nixon's demise and the Deep Throat mythology, in a way that light-hearted historians and clueless comedy lovers can both appreciate. "We have a very important school report on turquoise jewelry due in two days, and we can't find any books on it, and the President's having us followed. It's too much pressure!" ” - Sara NK
 
16.
Best in Show (2000)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A colorful array of characters compete at a national dog show. (90 mins.)
“ Oh, man. My favorite of the Christopher Guest films, I don't even understand how it can be so flingin' flangin' funny in a world very few of us know anything about - fancy dog shows. Each dog and its owners bring a new kooky, just believable enough color to the story, and with an all-star cast of comedic actors, this movie deLIVers. Goodbye, I have to go watch it again right now. ” - Sara NK
 
17.
Bring It On (2000)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A champion high school cheerleading squad discovers its previous captain stole all their best routines from an inner-city school and must scramble to compete at this year's championships. (98 mins.)
Director: Peyton Reed
“ This movie is so awesome stupid perfect that Kirsten Dunst's limited comedy chops can't even hurt it. Beautifully tongue in cheek while staying adorable, "Bring It On" is a cornucopia of teen goofiness and ludicrous one-liners. Abandon your inner critic, grab your spirit stick, and embrace the joy of the T-T-T-Toros, and the joys of cheerocracy. ” - Sara NK
 
18.
Zoolander (2001)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
At the end of his career, a clueless fashion model is brainwashed to kill the Prime Minister of Malaysia. (90 mins.)
Director: Ben Stiller
“ Ben Stiller stuff usually makes my skin crawl, cuz they always involve situations that could have been resolved by just using big boy words. But this character piece is his opus, in my humble opinion, and brings us countless memorable lines and scenes that are too, too brilliantly stupid. E.g., the freak gasoline-fighting accident. Bwahaha I can't even think about that and not laugh. I know, because I just tried. ” - Sara NK
 
19.
Austin Powers in Goldmember (2002)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Upon learning that his father has been kidnapped, Austin Powers must travel to 1975 and defeat the aptly named villain Goldmember - who is working with Dr. Evil. (94 mins.)
Director: Jay Roach
“ The movie my husband took me to on our first date, so for me, lots of nostalgia - also amazement that he would dare gauge our compatibility first and foremost with this crazy, ludicrous movie. Good news is, we both laughed so hard, we cried. Now we're married. Thank you, Goldmember. ” - Sara NK
 
20.
Jackass: The Movie (2002 Documentary)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Johnny Knoxville and his band of maniacs perform a variety of stunts and gross-out gags on the big screen for the first time. (87 mins.)
Director: Jeff Tremaine
“ The only documentary you will laugh all the way through. Whenever you're not busy gagging. I thought I would hate this thing, then I laughed my butt off in a theatre that was laughing its communal butt off, and a new respect for grossness and daring/stupid boy culture was born. Hats off, you insane, insane men. ” - Sara NK
 
21.
Anchorman: The Legend of Ron Burgundy (2004)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Ron Burgundy is San Diego's top-rated newsman in the male-dominated broadcasting of the 1970s, but that's all about to change for Ron and his cronies when an ambitious woman is hired as a new anchor. (94 mins.)
Director: Adam McKay
“ Soak up some classic and original Will Ferrell...before he dove into the "lamely parody every sport under the sun" era. Anchorman is the best. The supporting cast is amazing, quotable quotes are multiple per minute, and the ridiculousness is just enough where you have a great time but rarely want to roll your eyes. Mostly, you want to play along. Stay classy, San Diego. I love lamp. ” - Sara NK
 
22.
Napoleon Dynamite (2004)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A listless and alienated teenager decides to help his new friend win the class presidency in their small western high school, while he must deal with his bizarre family life back home. (96 mins.)
Director: Jared Hess
“ Whether or not you hate this indie surprise, there is no denying that it created a whole new subgenre of comedy - awkward and under-produced. There is something so homey about it, like watching television from the 70s...they're not trying to impress you, they're just doing whatever they feel like they wanna do, gosh! ” - Sara NK
 
23.
Kung Fu Hustle (2004)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
In Shanghai, China in the 1940s, a wannabe gangster aspires to join the notorious "Axe Gang" while residents of a housing complex exhibit extraordinary powers in defending their turf. (99 mins.)
Director: Stephen Chow
“ Are you kidding me. Could a movie be more awesome? A Chinese action/comedy that makes this LA lady's list? With SUBTITLES? If you know not what I mean, stop screwing around and watch this immediately. This is not a joke. ” - Sara NK
 
24.
Forgetting Sarah Marshall (2008)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah's traveling to the same resort as her ex - and she's bringing along her new boyfriend. (111 mins.)
“ Charming hilarity from Team Apatow, with a non-Apatow writer and non-Apatow director...resulting in awesomeness. Mila Kunis is adorable, Jason Segel is lovable, Russell Brand is Russell Brand, and Paul Rudd is hy-ster-i-cal. Take out the Jonah Hill parts, throw in more Paul Rudd, and you've got a perfect comedy. Apatow should keep writing those checks and let his JV team take over more often. ” - Sara NK
 
25.
(500) Days of Summer (2009)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her. (95 mins.)
Director: Marc Webb
“ So fresh, so playful, even the weaknesses of this film are endearing. It sheds light on universal themes like desperation and longing, as well as power dynamics within love, eventually landing on the relieving lesson of what is meant to be, will be. AND FUNNY! It's just a winner. And I dare you not to love that Joseph Gordon-Levitt. ” - Sara NK