Weller made his feature acting debut in the lead role of a 1960s activist for homosexual rights who finds himself an eyewitness to history in "Stonewall" (1995), a fictionalized account of the 1969 police raid on a Manhattan gay bar that sparked the modern gay rights movement. His subsequent film roles in the 90s were mostly small parts (i.e., "Basquiat" 1996; "Armageddon" 1998). The actor fared better on stage as he amassed an impressive resume, including sharing an OBIE award with the rest of the cast of the black comedy "Curtains" in 1996 and appearing opposite Stockard Channing in the 1997 Broadway revival of "The Little Foxes". On the small screen, Weller had a leading role in the 1997 Showtime production "Elmore Leonard's The Gold Coast" and played a Russian cab driver caught up in the action of "Aftershock: Earthquake in New York" (CBS, 1999).

Weller began the new millennium landing a part in the Jerry Bruckheimer-produced "Coyote Ugly" (2000), but the actor was disappointed to learn his role ended up on the proverbial cutting room floor. He fared somewhat better as Brian Wilson in the ABC biographical miniseries "The Beach Boys: An American Family" (2000), although some critics felt the lanky actor lacked the required heft to completely capture the eccentric singer-songwriter. Weller next popped up as Jacob in the biblical miniseries "In the Beginning" (NBC, 2000) but was overshadowed by more colorful co-stars. The actor did enjoy good notices for his turn as an oleaginous headhunter who may not be quite as slimy as he appears in the Sundance-screened "The Business of Strangers" (2001). Weller also received critical kudos for his performance as a jockish somewhat abrasive college student in Neil LaBute's stage play "The Shape of Things" which was performed in both London and NYC. He continued in the collegiate vein, playing a frat boy in "The Pink House" (lensed 2001).