Taj Badalandabad (Kal Penn), the personal assistant to local hero Van Wilder, has just graduated Coolidge College and is now on his way to England's Camford University. Taj plans to follow in the footsteps of his father — not only by obtaining a degree, but also to become a member of an exclusive campus Fraternal Guild, the Fox and Hounds, where Taj hopes he will become the next generation of Badalandabads to be deservedly nicknamed the "Sultan of Snatch."
However, when Taj arrives at Camford, he is told by Pip Everett, the Earl of Grey (Daniel Percival), the arrogant leader of the Fox and Hounds, that there had been a mistake and he has actually not been accepted into the Fraternal Guild.
Heartbroken, Taj, with his faithful bulldog Ballzac in tow, instead takes the only housing opening available on campus and becomes the "Head of House" for a group of student misfits — Sadie (Holly Davidson), a gorgeous but foul-mouthed Cockney girl, Seamus (Glen Barry), an English-hating Irishman, Gethin (Anthony Cozens), a nerd, and Simon (Steven Rathman), a kid who rarely talks.
Stuck with a band of misfits, Taj considers what Van Wilder would do in the same unpleasant situation, and in classic "Van" fashion he decides to take on the challenge and turn the house around. At the campus Society Inaugural Ball, Taj announces to the pompous crowd that he and his new friends are starting their own exclusive society — the Cock and Bulls. In addition, the Cock and Bulls declare that they are going to compete in the venerable Hastings Cup, an ongoing series of campus academic events and athletic competitions.
Also, as part of his duties, Taj finds out that he will be a history teacher to his new friends and that his teaching supervisor will be Charlotte Higginson (Lauren Cohan), an English beauty who just happens to be dating Pip Everett. Taj is instantly attracted to Charlotte.
Taj and Charlotte clash over Taj's unconventional teaching methods until Charlotte points out that his new friends are in danger of flunking out of school because their grades are so low. Taj takes Charlotte's challenge to heart and starts turning them around — their grades as well as their self-esteem.
Meanwhile, much to the fury of Pip Everett, not only are the Cock and Bulls catching up to the Fox and Hounds in the Hastings Cup, but Taj and Charlotte are spending a lot of time together.
Pip sets out to get rid of Taj by attempting to humiliate him at the Royal Literary Ball and then sabotaging Ballzac at the Camford Dog Show, but both cases backfire and Pip ends up the one embarrassed. Much to Pip's dismay, Taj and Charlotte are clearly falling in love and the Cock and Bulls are moving into a close second behind the Fox and Hounds.
Pip decides to set up Taj and the Cock and Bulls by planting stolen test exams in their house. The plan works temporarily, and they are about to get expelled until Taj steps up and takes the blame for the theft — on the condition that his team are allowed to stay in school. The school Provost agrees to the terms, and Taj has to leave Camford. Angst-ridden, Charlotte tells Taj she never wants to see him again.
The Cock and Bulls are now left to compete in the final event of the Hastings Cup without their courageous leader. But when Charlotte finds evidence that proves Taj's innocence, she and Taj rush to the Hastings Cup, just in time for Taj to compete against Pip in the final event — fencing.
An angry and vengeful Pip makes sure that the fencing match degenerates into an all-out sword fight, but in the end, Taj defeats Pip and the Cock and Bulls win the Hastings Cup. Pip gets expelled for planting the exams while Taj and Charlotte happily begin a new life together.
In November 2006, Kal Penn and musicians Art Alexakis of Everclear and Jonny Dubowsky of Jonny Lives! toured college campuses, radio and television stations across the country promoting the film. A month-long 21-date Van Wilder Rock Tour headlined by Everclear and Jonny Lives!, started in January 2007 and ran through the end of February. The tour promoted the film and its soundtrack.
The film was not a hit with either critics or audiences. It has a "rotten" 7% rating at Rotten Tomatoes and it earned just $2.3 million in its opening US weekend. Despite the sequel's poor critical reception and modest box-office success, a third Van Wilder film, National Lampoon's Van Wilder: Freshman Year, was shot in 2008 in Atlanta, Georgia. It was released straight to DVD on June 2, 2009 with mixed reviews.