A veteran of high school and local stage productions, Webber made an auspicious big screen debut in Philadelphia director Eugene Martin's independent "Edge City", a gritty look at exploding tensions between city kids and their suburban counterparts hailed for its non-exploitative realism. The actor next took a role in the somewhat similarly themed Iowa-set "Whiteboys" (1999), an ambitious feature telling the story of a trio of hip-hop influenced farm boys who dream of hanging with rap artists and seek to prove their street cred as drug dealers in Chicago's notorious Cabrini Green housing project. Cast alongside fellow up and comers Danny Hoch and Dash Mihok, Webber played the most affluent of the group, a disaffected middle class teen. Next up for Webber was a supporting role in the teen romantic comedy "Drive Me Crazy" (also 1999). A starring vehicle for sitcom heavyweight Melissa Joan Hart, the movie suffered from dire predictability, but Webber's portrayal of 'Designated' Dave, a conscientious computer buff so-named for his willingness to drive friends home, was among the feature's highlights. He made his starring debut in the disappointing "Snow Day" (2000), playing Hal, a young lovestruck high schooler who sets out to use this weather-defined holiday to his romantic advantage. Webber's affable performance, though, couldn't save the formulaic, curiously unfunny film from box office failure.
While his early outings were less than stellar, Webber displayed a talent that would carry him through and no doubt offer a promising career. Further proof was provided by his turn as Bobby in David Mamet's classic "American Buffalo", staged in London at the famed Donmar Warehouse and in Off-Broadway in New York at the Atlantic Theater in 2000. Webber was roundly praised for his appropriately excitable take on this challenging role. The actor could next be seen with Laurel Holloman and Elise Neal in the World War II era coming-of-age drama "The Rising Place" (lensed 1999).