The low budget shop Cannon Films gave Stockwell the opportunity to write and direct features. He starred as the leader of a group of teenage vigilantes in the suspense thriller "Dangerously Close" (1986) which he co-wrote with Scott Fields and Marty Ross. Fields and Stockwell went on to become a screenwriting team, although only one other effort has been produced: "Under Cover" (1987), a pallid effort about a cop investigating a high school drug ring, which also marked Stockwell's directorial debut. He returned to the other side of the camera in the direct-to-video drama "Born to Ride" and the Italian-produced feature "Miliardi" (both 1991). He headlined the "Rashomon"-inspired indie, "I Shot a Man in Vegas" (1994) and played a cameo role as a White House staff member in Oliver Stone's "Nixon" (1995).
On TV, Stockwell was Billy Hazard, a Northern soldier fighting in the American Civil War, in the ABC miniseries "North and South" (1985) and co-starred as a member of the "Billionaire Boys Club" (NBC, 1987), a group of arrogant young investment partners who turn to murder. He has also been seen in the TV-movies "Quarterback Princess" (CBS, 1983), as Helen Hunt's boyfriend, and alongside Stefanie Powers and Robert Wagner in "Hart to Hart: Crimes of the Hart" (NBC, 1994).
In the early 90s, Stockwell had all but abandoned acting in favor of pursuing a music career as front man for the band The Brood. When he did return to movies and TV, he worked infrequently preferring to develop his burgeoning reputation as a screenwriter and director. He penned the darkly humorous script for HBO's "Breast Men" (1997), about the inventors of silicone implants which became his calling card. He wrote and directed the equally well-received drama "Cheaters" (HBO, 2000), about a teacher who uses an illegally obtained copy of test questions to level the playing field in an academic competition. His taut, nicely nuanced script snagged an Emmy nomination. Stockwell went on to helm "crazy/beautiful" (2001), a contemporary spin on "Romeo and Juliet" starring Kirsten Dunst and Jay Hernandez, and write the screenplay for "Rock Star" (also 2001), about an ordinary guy who harbors a desire to play in a heavy metal band.