Olds went from the New York-filmed series to a shot on Broadway, making his debut in the drama "Any Given Day". Already enrolled at Yale, the actor took time off for the opportunity to work on stage. Less auspicious was his film debut, the misfire Jason Priestley vehicle "Calendar Girl". A nostalgic take on the teen road trip, the film proved neither funny nor touching, and was a disappointment for the audience as well as all those involved. Back at Yale, Olds took on the ambitious senior project of starring in and directing the rarely produced Shakespeare drama "Richard II", and received positive notices from attendees for his efforts. More TV work followed for the young actor in 1996, when he had a supporting role in John Frankenheimer's Civil War prison camp-set miniseries "Andersonville" (TNT) and guest starred on the series "Party of Five" (Fox) and "Sisters" (NBC). He took on independent feature work, with starring roles in the small-town tale "35 Miles From Normal" and the disturbing morality drama "The Animal Room" (both released 1997).
From 1997-1998, Olds returned to the stage, co-starring in Arthur Miller's "A View From the Bridge" at the Roundabout Theater. Olds played Rodolpho, an opera singing illegal immigrant with designs on Brittany Murphy's Catherine that her Uncle Eddie (Anthony LaPaglia) finds suspicious. Some reviewers thought his characterization was a bit over the top, but the actor was largely well-received and happy with his work. After a starring role in the Sci-Fi Channel's "A Town Has Turned to Dust" (1998), a TV presentation of Rod Serling's "Playhouse 90" psychodrama, he took a supporting role opposite Billy Crudup in the track and field-themed Steve Prefontaine biopic "Without Limits" (also 1998). In 2000, "Law & Order" producer Dick Wolf came calling with another opportunity for Olds, whom he saw as the star of his young political drama series "D.C." The actor was tapped to play Mason Scott, a privileged idealist with political aspirations and a flaky twin sister (Jacinda Barrett) and pragmatic roommate (Mark-Paul Gosselaar). Unfortunately, the series was cancelled after only three episodes. Down but not out, the still up and coming Olds could count on a featured role as a soap opera actor in the promising gay-themed independent drama "Urbania" (2000) to get his career back on track.