While Wilson found some initial success as a film actor after his turn as Dignan in Bottle Rocket, he also remained a key creative collaborator in Wes Anderson's next two directorial efforts. Rushmore was the two writers' second script collaboration. Although Wilson didn't appear in the film, he and Anderson acknowledged on the Criterion Collection DVD audio commentary that Wilson has a sort of quasi-cameo as Rosemary Cross's dead husband, Edward Appleby. When Max Fischer visits Miss Cross in Appleby's boyhood bedroom, photographs of a young Owen Wilson are incorporated in the set for the scene.

Wilson quickly landed roles in big-budget movies such as The Cable Guy, directed by Ben Stiller, an early admirer of Bottle Rocket. After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor in Permanent Midnight, which starred Stiller as a drug-addicted TV writer; and a role as a serial killer in The Minu