American Pie – It may seem uncouth, it may seem unlettered, but intercourse with a pie could have potential perks. This scene, from this teenie movie to end all teenie movies, has become the latent fantasy of many a pre-pubescent male. This movie gave us Stifler, a gentlemen who enacts his will wantonly, and with debonair. We all need to recapture the disgraces of our youth from time-to-time. This film helps us do just that

Director: Paul Weitz
Release date: 9 July 1999
Cast: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Alyson Hannigan, Shannon Elizabeth, Tara Reid, Sean William Scott

Anchorman – The Legend Of Ron Burgundy – Maybe Will Ferrell’s funniest character to date, the misogynistic anchorman has been featured extensively on the comedian’s Funny Or Die web site. A cast featuring cameos from Ben Stiller, Vince Vaughn and Jack Black as a peeved biker only helped to elevate a film, which set new standards for chat-up lines. With such classics as “I am very important. I have many leather bound books and my apartment smells of rich mahogany…” and “I want to be on you,” Anchorman became a staple for laugh out loud slapstick.

Director: Adam McKay
Release date: 9 July 2004
Cast: Will Ferrell, Christina Applegate, Paul Rudd, Steve Carell, David Koechner, Fred Willard

The Big Lebowski – A hapless pariah whose sole refuge happens to be a bowling alley gets enmeshed in another mans problems after intruders soil his rug. ‘The Dude’ can teach all of us a thing about grace under pressure. The Big Lebowski is why people still order White Russians.

Director: Joen & Ethan Coen
Release date: 6 March 1998
Cast: Jeff Bridges, John Goodman, Julianne Moore, Steve Buschemi, David Huddleston, Phillip Seymour Hoffman, Tara Reid

Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan – Sacha Baron Cohen completely owns this character from Kazakhstan. Unleashing his antics on unsuspecting Americans you can’t help but laugh, however, at times the prejudices that still linger in the country are so painfully obvious. Outrageous in nature, Borat will have you aching to see how far he will go next and wondering what cheese made of breast milk might taste like.

Director: Larry Charles
Release date: 3 November 2006
Cast: Sacha Baron Cohen, Ken Davitian

Clerks – Even the most savoir fare of us all must acquiesce to the truths of suburban living. Clerks makes us do just that. Dante and Randall spend a day pondering just how many innocents died when the Death Star blew up (and other important questions), while Dante desperately tries to reconcile the dilemma of deciding between the woman he has and the woman he wants to have. It sounds so faux pas, but Kevin Smith directed it. And he, my friends, parallels the suave of Hugh Hefner.

Director: Kevin Smith
Release date: 19 October 1994
Cast: Brian O’Halloran, Jeff Anderson, Jason Mewes, Kevin Smith

Detroit Rock City – This is one of the new classics, a story almost as timeless as music itself. Four young KISS fans are deprived of tickets to a KISS show and go through hell and back just for a chance to see their idols. A lot of people dismissed it as just another teen film the first time around, but it has a powerful message about growing up and becoming more than just a scared teenager. Sometimes it takes your mother destroying your concert tickets to teach you how to stand up and be a man.

Director: Adam Rifkin
Release date: 13 August 1999
Cast: Edward Furlong, Sam Huntington, Giuseppe Andrwes, James deBello, Melanie Lynskey, Natasha Lyonne, KISS

Friday – Forget the sequels, this is the definitive hood movie. Ice Cube plays Craig Jones, a man who just manages to have the worst day ever. Wrongly fired from his job, and indebted to a neighborhood drug dealer thanks to his well-meaning friend Smokey, Craig has to scrounge up the money needed and just get through the day.

Director: F. Gary Gray.
Release date: 27 April 1995
Cast: Ice Cube, Chris Tucker, Nia Long, Faizon Love, Tiny Lister Jr.

The 40-Year-Old Virgin – This is the movie that set it off for Judd Apatow. Host to many great gags and featuring actors Seth Rogen, Paul Rudd, and Jonah Hill, who all went on to star in their own features. The best part of the movie is that you probably know someone just as awkward and just as virginal as Andy.

Director: Judd Apatow
Release date: 19 August 2005
Cast: Steve Carell, Catherine Keener, Paul Rudd, Seth Rogen, Elizabeth Banks, Leslie Mann

Galaxy Quest – Spoofing Star Trek and starring Tim Allen, this movie combines humor and sci-fi for an original and entertaining film. Taking a look into fandom in general with science fiction fans, it is seemingly very accurate and funny to boot. Instead of being despised by fans of Star Trek, it was applauded for its candid take at fandom culture.

Director: Dean Parisot
Release date: 23 December 1999
Cast: Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub

Half Baked – Who the hell doesn’t like Dave Chappelle? In his first and only leading role in film, Chappelle is his usual hilarious self. Want to find out how to go on a date with just $8 in your pocket? Learn what a fully is? Or see what Billy Bong Thorton looks like?

Director: Tamra Davis
Release date: 16 January 1998
Cast: Dave Chappelle, Guillermo Diaz, Jim Breuer, Harland Williams

The Life Of Brian – One of the films on the shortlist for ‘Greatest Comedy Of All Time’. The Monty Python team set out to make a film about what they believed was the danger of overzealous adherence to religion and ended up committing blasphemies at an unprecedented rate. George Harrison of The Beatles served as executive producer on the film, but even a member of the band that was once ‘bigger than Jesus’ could not divert from the controversy. A number of lost scenes that were rediscovered in 1998 would only have further fueled the fire.

Director: Terry Jones
Release date: 17 August 1979
Cast: Graham Chapman, John Cleese, Terry Gilliam, Eric Idle, Terry Jones, Michael Palin

O Brother, Where Art Thou? – A reimagining of Homer’s Odyssey, three convicts evade the greased palms of the law in the mid 1930s. George Clooney gives an otherwise pedestrian film that greatly needed metropolitan definition.

Director: Joel & Ethan Coen
Release date: 22 December 2000
Cast: George Clooney, John Turturro, Tim Blake Nelson, John Goodman, Holly Hunter

Office Space – Mike Judge has caught some flack for some of his work but he comes out well ahead after Office Space. This is the definitive office comedy in the pre-Steve Carell / Michael Scott era, a rallying cry for frustrated office workers. Ron Livingston’s everyman whose frustration climaxes in an absurdic Superman III-inspired embezzlement scheme is perfect. The movie pokes fun at everything from the passive-aggressive office discipline structure to indecipherable computer error codes (PC Load Letter? What the f— does that mean?). The film sits somewhere between biting social satire and wish fulfillment and has just enough of both. A must for everyone who has ever worked in an office.

Director: Mike Judge
Release date: 19 February 1999
Cast: Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu, Stephen Root, Gary Cole, John C. McGinley

Sideways – A fervent wino, doubling as an aspiring novelist, takes his soon-to-be-wed university buddy on a road-trip through the Napa Valley, California’s burgeoning wine county. All those with refined pallets and a taste for barrel-aged reds should indulge in this mordant little film.

Director: Alexander Payne
Release date: 28 January 2005
Cast: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh