Van Wilder: Freshman Year is a 2009 prequel to the 2002 film National Lampoon's Van Wilder. The film follows the adventures of Van Wilder during his freshman year at Coolidge College, where he is determined to make the most of his college experience. However, he quickly realizes that the school is ruled by the strict and conservative Dean Reardon, who has banned all forms of partying and sexual activity on campus.
Despite the challenges, Van is determined to have his way and sets out to organize the biggest party the college has ever seen, all the while attempting to win the heart of Kaitlin, the attractive and intelligent head of his debate team. He also befriends his roommate, Farley, and a number of other misfits who are equally keen on breaking the rules and having some fun.
As Van's party planning and dating efforts heat up, he runs afoul of Dean Reardon, who becomes determined to put an end to Van's disruptive antics once and for all. With the help of his friends, Van must outmaneuver the dean while also facing his own personal demons and trying to come to terms with his own future.
The film features a cast of up-and-coming actors, including Jonathan Bennett as Van, Kristin Cavallari as Kaitlin, and Steve Talley as Farley. It received mixed reviews from critics but has become a cult classic, especially among fans of the original Van Wilder movie.