Despite opening to tepid reviews, Old School has since benefited from the emergence of the Vaughn-Ferrell-Stiller-Wilson "frat pack" that gave rise to the recent spate of super-popular R-rated comedies. It is a sophomorically funny movie that gets better with each repeated viewing.
What's missing from the analysis of Old School is that it's also one of the most unapologetically anti-marriage films of all time. The movie opens with Luke Wilson's character about to propose marriage, a plan that is dashed when he returns early from a business trip to catch his girlfriend engaging in a gang-bang. Will "Frank the Tank" Ferrell's marriage implodes within weeks of his wedding, a pact that Vaughn the only character to remain wed throughout (albeit miserably) tries to head off at the altar by providing Ferrell with the horrifying thought that marriage equals "one vagina for the rest of your life."
Beneath Old School's slapstick is a very serious message: that no one under the age of 30 should even begin to consider marriage. It's a plot point that recurs in Wedding Crashers, the smash-hit kicker to Vaughn's masterful trilogy.