Meyer lent his broken-nosed strong screen presence to several roles as a druggie starting with his debut in "Freddy's Dead: The Final Nightmare" (1991), in which he was memorably dispatched in a video game. His breakthrough screen role was as the skateboarding stoner (a homage to Sean Penn in 1982's "Fast Times at Ridgemont High") in "Clueless" (1995). Meyer offered similar characterizations in "The Craft" and "John Carpenter's Escape From L.A." (both 1996). He fared better as the best friend of an Olympic hopeful in the biopic "Prefontaine" (1997) and as a high school student yearning to leave his hometown in "Dancer, Texas Pop. 81" (1998). In the highly touted "54" (also 1998), a look at life in the famous 70s nightspot, the actor was cast as a sexy busboy married to the coat check girl (Salma Hayek) and pursued by a bartender (Ryan Phillippe)—Meyer is close friends with Phillippe, with whom he and Seth Green share a production company.

Meyer would subsequently appear as a supporting player in films including "Go" (1999) and "The Insider" (1999) before graduating to full-fledged leading roles in "Tail Lights Fade" (1999), as part of a pair of couples who travel across Canada to bail his girlfriend's brother out of jail, and in the mildly amusing "Road Trip" (2000), in which he again travels across country as a college student hoping desperately to retrieve a videotape of himself having sex with another girl, which was inadvertently mailed to the ex that he pines for. "Road Trip" marked the first instinct that Meyer's well-developed slacker sidekick persona had matured and could be tweaked to make him a full-fledged star. He was re-teamed with Amy Smart in yet-another racing cross country film, this time as part of the multi-plot ensemble of "Rat Race" (2001), a sort-of homage to the all-star screwball chase films of the 1960s like "It's a Mad, Mad, Mad World."

Meyer received his biggest break yet when he was cast as the lead in the NBC sit-com "Inside Schwartz" (2001) as a minor-league sportscaster whose dating life is illustrated by fantasy-driven sports highlights. Although aired in the cozy post-"Friends" timeslot on NBC's "Must-See" Thursdays, the critically reviled series failed to capture much of an audience and was cancelled after only a handful of episodes. Meyer quickly resurfaced in a winning supporting turn as Meg Ryan's brother in the whimsical fantasy-comedy "Kate & Leopold" (2001) and was tapped to provide the voice of the fabled wooden boy "Pinocchio" in the U.S. release of Italian writer-director-star Roberto Benigni's 2002 take on the classic tale. A second attempt at TV series stardom, "Married to the Kellys" (2003) about a New York man who suddenly finds himself surrounded by his bride's eccentric Kansas family, also met with little fanfare or ratings success (Meyer also appeared in the pilot of an even more notable 2003 TV failure, NBC's "Coupling" but opted to star in "Kellys" instead).

Returning to the big screen, Meyer took on the role of Jon, the hapless owner of the famed comic book cat in the film adaptation of "Garfield" (2004). In “Herbie: Fully Loaded” (2005), Meyer played the son of a NASAR champ whose racing slump threatens to put the brakes on the family legacy. It’s up to his sister (Lindsay Lohan) and a loveable Volkswagen Beetle to revive the family’s fallen glory. He was then set to appear in “Rebound” (2005), a Martin Lawrence laugher about an college basketball coach on the outs with his profession due to his uncontrollable temper.