Da Re's first role was in the TV movie Into the Homeland in 1987, which was directed by Lesli Linka Glatter, who would later go on to direct Da Re in the show that brought him fame, Twin Peaks. After a few more roles in TV movies he landed the role of Leo Johnson in the 1990 cult classic Twin Peaks, created by David Lynch. Da Re went on to work with Lynch again as a casting assistant for Wild at Heart (1990), as Leo Johnson in the Twin Peaks prequel, Twin Peaks: Fire Walk with Me (1992) and as a property buyer for Lost Highway (1997).