- Cult Classic: Didn't make big returns, but fans loved Ryan Reynolds as the titular character and its cult status eventually spawned two sequels.
- Hilarious in Hindsight: Ryan Reynolds has a bulldog named Colossus and lives in a school.
- Lauren Cohan would later star in Batman v Superman: Dawn of Justice as Martha Wayne, which led to the infamous “Save Martha!” moment in said movie. Eventually, Deadpool 2, starring Ryan Reynolds, would mock that scene.
- Moral Event Horizon:
- Richard smuggling underaged kids into one of Van's parties to get them drunk and frame Van.
- In the sequel, Pip trying to kill Taj with a real sword in the climax.
- The dean in Freshman Year crosses it when he tries to shoot Van and his dog near the end.
- Retroactive Recognition:
- Ryan Reynolds is Van Wilder in the original film.
- Simon Helberg (Howard Wolowitz, Moist) is Vernon, a member of the Lambda Omega Omega fraternity.
- Kal Penn (Kumar, Dr Lawerence Kutner) is Taj.
- Sophia Bush (Brooke Davis) is Sally, the co-ed Van makes out with during his Heroic BSoD.
- A drunken extra in a pink nightie is played by Aaron Paul (Jesse Pinkman).
- In the sequel, Lauren Cohan (Rose, Maggie Greene, Martha Wayne) plays Charlotte.
- Sequelitis: While the first film is now often hailed as an unsung gem, the same can't be said of the second or third films, which — despite the best efforts of Kal Penn in the second one — quickly fall apart without Ryan Reynolds around to elevate the material.
- Squick: Several examples such as the gag with Van's dog's testicles or some of Taj's dialogue involving himself and sex.
- Vindicated by History: On its initial release it was absolutely thrashed by critics, getting a Rotten Tomatoes rating of just 18%, and made decent, but unspectacular box-office returns. Nowadays, it's widely regarded as (with the arguable exception of Loaded Weapon 1) the best "National Lampoon's..." film made without the involvement of either John Hughes or Harold Ramis, and as an early example of Ryan Reynolds' comedic talents.
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