Making people laugh is much harder than making people cry. A comedy movie of high quality can be a more difficult thing. Below we list 6 comedy movies of high quality and you may want to pick out to see it again.

Part 1


The 40-Year-Old Virgin (2005): Directed by Judd Apatow

It’s a fairly one-note premise that could’ve been a fairly one-note movie, but as written by Judd Apatow and Steve Carell, The 40-Year-Old Virgin actually turned out to be a surprise smash and the start of the Apatow Empire in comedy. (Impeccably cast, it featured the likes of Seth Rogen, Kevin Hart, Jonah Hill, Jane Lynch, Kat Dennings, Elizabeth Banks and Mindy Kaling all before they were household names.) You don’t need to look any further than the film’s iconic poster to get an idea of what The 40-Year-Old Virgin was after: a raunchy comedy wrapped in a sweet package. While Apatow’s work has been unfairly stereotyped as bro-comedies about manchildren, Virgin is very much a warm, romantic comedy masquerading as a vulgar sex romp. With several famous improv-heavy riffs — like Carell getting his chest waxed while screaming non-sequiturs like “NOOOO KELLY CLARKSON!” — the film helped usher in a new era of comedy, where directors cast funny people and get out of their way. Virgin may not have the “message” of later Apatow films, and it may be better for it.


Office Space (1999): Directed by Mike Judge

Funny or Die recently got the real Michael Bolton to play “Michael Bolton,” David Berman’s hapless corporate drone from Mike Judge’s Office Space. It was a really entertaining clip, but with or without the maestro of “When a Man Loves a Woman,” the film is still one of smartest comedies of the last 25 years. After breaking through to the mainstream as the man behind Beavis & Butt-head, Judge crossed over from animation to live-action by adapting one of his very first cartoons, a short about a frustrated office worker named Milton. In the feature, Milton (Stephen Root) became a supporting player in the story of Peter Gibbons (Ron Livingston), a miserable computer programmer who breathes new life into his moribund career when he stops giving a damn about his job. Audiences were similarly indifferent to Office Space when it premiered in theaters in 1999, but it quickly accrued a cult following thanks to its brutally sharp depiction of corporate bureaucracy and the endless indignities suffered by the human cogs in our capitalistic machine. All it took was a little time, love, and tenderness.


Bad Santa (2003): Directed by Terry Zwigoff

Other Christmas comedies may be repeated more frequently on television (Elf) or really repeated more frequently on television (A Christmas Story), but none can match the madness of Bad Santa. Though its screenplay is credited to Glenn Ficarra and John Requa, the film was heavily rewritten by Joel and Ethan Coen, and their dark sense of humor is felt throughout the film. Who else would end a Christmas comedy with the main character getting shot multiple times on a little kid’s front lawn? Bad Santa was a troubled production — the Coens fought with the Weinsteins over casting, director Terry Zwigoff was replaced for reshoots — and yet somehow it all worked. In many other filthy comedies, the vulgarities can seem forced. When you don’t have a joke, just say the F-word. But Billy Bob Thornton’s Willie feels as lived-in as his urine-soaked Santa costume, and every foul thing that comes out of his mouth rings true — and will always make you laugh.


There’s Something About Mary (1998) Directed by Bobby and Peter Farrelly

Memory: It is the summer of 1998. I am 14. We live in Las Vegas, so everything is hot and boring and horrible in the summer, except for the cool breezes that waft through the local multiplex. Movies are therefore a no-brainer, and the raunchy There’s Something About Mary is the only new release in the middle of July, making it even more of an obvious choice. I laughed until I nearly peed my pants, and until the woman next to me (Hi, Mom!) laughed so hard she actually sobbed. I’d never laughed like that in a theater before and I haven’t laughed like that since, a full-body hysteria that marked me as a Farrelly brothers fan for life. To this day, I cannot resist balls being trapped in zippers and hair being styled by bodily fluids, horrible and revolting as it all may sound.


Observe and Report (2009): Directed by Jody Hill

Observe and Report is Taxi Driver filtered through the eyes of Jody Hill, who is uniquely skilled at capturing the lives of socially inept and delusional wackos. (See also: The Foot Fist Way, Eastbound and Down.) You probably know a guy like Seth Rogen’s Ronnie Barnhardt, a determined mall security guard who transforms his insecurities into unjustified arrogance. What makes Observe and Report so funny is that neither Hill nor Rogen shy away from the darker side of Ronnie’s personality; Hill picks at aspects of Ronnie’s character that are horrifying and cringe-inducing. Ronnie wants the job. He wants the girl. He wants the recognition he believes he deserves from years spent with his pill-addled mother (a massively funny Celia Weston). Ronnie’s obsessive nature drives him to violent zealotry in the pursuit of a serial flasher, and a series of escalating awful choices that culminate in the worst act of misguided heroism in film history, eliciting that perfect response of uncomfortable laughter derived from the disbelief that someone could be this monumentally stupid. 


Election (1999): Directed by Alexander Payne

Alexander Payne’s brilliant Election is a scathing look at the motivations and desires of the sort of brown-nosing overachievers we all knew in high school. Tracy Flick is one of cinema’s greatest villains and one of Reese Witherspoon’s best roles; her all-American, milk-fed looks and her big, hopeful blue eyes make Tracy all the more sinister. How could this aspiring role model and dedicated student be so damn evil? The way she torments Matthew Broderick’s nebbish teacher is hilariously horrible, but watching Jim McAllister crumple and devolve into something far more pitiful holds a certain schadenfreude-ish delight. While watching the inherently likable Broderick play off Witherspoon’s golly-gee-mister manipulations is exceptionally entertaining, the film’s supporting cast is equally as great. Chris Klein is perfectly cast as an empty-headed and naive jock, while Jessica Campbell makes an impeccable angsty teen resentful of her more prosperous peers. Through her pursuit of winning the school election to become student body president, Tracy brings out the worst in Mr. McAllister, but she doesn’t destroy his life; he destroys his own.


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