Liman became attached to direct Swingers when its screenwriter Jon Favreau turned down offers from studios who wanted to cast established actors. The director agreed to cast Favreau and his friends (Vince Vaughn, Ron Livingston, and Patrick Van Horn) in this comedy about struggling actors amid the L.A. club milieu. The result was a $250,000 dialogue-propeled film that became a sleeper hit and critical success. In addition to establishing a cult following, it jump-started the careers of the featured actors.

Liman's next effort, Go (1999) tracked the events of one night through three different and points of view as plot lines diverged and reconverged; doing double duty as cinematographer. The film made a profit at the box office grossing $28.4 million worldwide against a $6.5 million budget.

In 1999 Liman shot a commercial for Nike in which Tiger Woods, without letting the ball touch the ground, repeatedly bounced a ball on his club and then drove it into the distance.