A Dare to be Great Scenario
There should be no doubt that Ryan Reynolds was always going to be a star. You see him now, while his deep filmography and diversified business portfolio (owning pieces of a gin company, a telco, a soccer team, and a television streaming station) and you get the idea the man had the savvy to not only make it big but the parlay that into a successful, and long lasting, career. His early works may not have illustrated just how far he was going to go (although I did enjoy Two Guys, a Girl, and a Pizza Place when it aired) but what he needed was a solid, break out role, to really launch him into his next phase (and towards the career he has now).
That film was Van Wilder. Produced under the "National Lampoon" brand (making this National Lampoon's Van Wilder, technically), the film is a legitimately funny hang out film, but that's entirely down the Reynolds himself. If you were to make the same film without Reynolds in the lead role is simply wouldn't work. We have empirical evidence of just that as two follow ups for this film were made: The Rise of Taj, an okay movie with a game Kal Penn taking over the lead, but it doesn't have the same spark; and Freshman Year, which recasts the Van Wilder role and proves how essential Reynolds's performance is to selling the character.
The fact is that, in the wrong hands, Van Wilder would come across as a conceited douche. He's a perpetual student who doesn't want to leave his school, instead spending seven years without getting a bachelor's degree, all while partying and loving life. And, of course, it costs his father $40k a semester to send his son to school (a fact raised early in this film), so Van isn't just a conceited douche, he's also a spoiled rich kid. You have to have the right actor to pull that off. Reynolds is the right actor for that task, adding in an innate sweetness (along with his absolutely on point comedic timing and reactions) that sells the character. You can't hit that kind of perfect casting twice. So it's a good thing it works so well here.
Van Wilder features its titular character (played by Reynolds) at the start of his seventh year at Coolidge College. In his time at the school he's made quite the name for himself, putting on parties and fundraisers, making Coolidge his home and wearing it around him like a cloak. Everyone knows him, almost everyone loves him, and many would willing fall at his feet to work for him. That's how Van meets Taj (Kal Penn), a Indian exchange student in from Badalamdabad, who wants to work for Van as his assistant. He also wants Van to teach him how to meet women (although the film lets him put it in far more crass, and hilarious terms), something Wilder has no small skill at.
Having been there for seven years, and having built up a bit of a reputation, the story on Wilder is assigned to Gwen Pearson (Tara Reid), reporter for the school paper. her job is to get the story of Wilder, everything that makes him tick, even as Van tries his best to avoid interviews. But there is a spark between Gwen and Van, something neither of them can deny. This irks her boyfriend, Delta Iota Kappa (DIK) president Richard Bagg (Daniel Cosgrove), who will go to great lengths to try and tear Wilder down. It's slobs vs. snobs in an ivy league school with the fate of Coolidge, and Van's own academic career, somehow hanging in the balance.
There are a lot of elements to Van Wilder, giving it a very shaggy, hung together construction. There are two threads that could arguably be considered main stories that drive the film forward -- Van needing to earn money to keep himself in school after his father cuts off the money, and the love story between Gwen and Van -- although it's hard to say those are really true plots. The whole of the film is done in a loose, skit-like format, keeping everything flowing without necessarily needing strong connective tissue. It's a collection of funny scenes instead of a tightly directed story.
That doesn't necessarily hold the film back, though, because the scenes are, by and large, funny on their own. The various parties Van throws, the small moments between him and his friends, the various scenes of revenge he takes on Richard, all of them are generally quite funny and carry each moment forward on their own. The loose construction lets the film follow whatever ideas it has all while enjoying all that could be done with this character in this setting this way. It works.
Of course, it is Reynolds that helps to sell the whole of the film. Enough can never be said about the way he's able to sell every moment and every scene in the film. He has a way with his line deliveries, with his reaction shots, with his general presence that can add humor to every moment. This should be obvious to anyone that has seen Deadpool or, really, any film he's ever been in. He's just a natural comedic talent that can elevate any material. Watching Van Wilder you can see how he'd eventually go on to bigger and better things as everything about his stardom is contained here, in this littler film.
With that said, there are flaws to the film that are hard to ignore on repeat viewings. While I like Kal Penn as an actor, his role as Taj is severely underwritten. He most hangs out to make cunnilingus jokes and get into trouble. Penn sells it for all its worth (and you can see why, after this film and then Harold & Kumar Go to White Castle, Taj was given the lead in the Van Wilder sequel), but there just isn't enough here for Taj to do. Still, he comes across better than Tara Reid's Gwen as Reid is never able to play her character in any convincing way. You don't buy her as a reporter, or as a love interest, or as a real human being. She was horribly miscast.
And as much as I enjoy the film, there is one scene in particular that is (pun intended) hard to stomach. There are plenty of sophomoric skits and dumb jokes in the film, but one scene in particular (involving a dog and some eclairs) goes to such a depraved place that it, and its immediately follow up scene, are nauseating. It's funny, yes, and some of the line deliveries during and after this sequence make the whole affair more... palatable? But its still a stomach turning moment that I struggle to watch every single time. It's just gross.
Still, I've watched this film easily five or six times since it came out, and I find every few years I go back to it again. There's easy chemistry among the leads, and a lot of humor to be had. The film gets you laughing early and keeps you going all while Reynolds's assured presences keeps the whole production moving along. This was one of the last great films from the National Lampoon brand (because they sold their name to any direct-to-video production house that would pay) and that's all down to Reynolds. Without him the film would be unwatchable. Because of this film, though, the star got his big moment and never looked back.