His next produced script, the action comedy "Midnight Run" (1988), was based on an idea he had during a particularly difficult flight to L.A. The box-office hit starred Robert De Niro as a bounty hunter tracking a mob-connected embezzler played by Charles Grodin. It later spun off into several installments in the syndicated "Action Pack" TV-movie series, which Gallo executive produced.

With "29th Street" (1991), Gallo made his directorial debut, working from his script based on a true story related to him by actor Frank Pesce. The feature was well-received and marked an auspicious debut for Gallo. In 1994 Gallo became a triple threat when he wrote, produced and directed "Trapped in Paradise" about three brothers who plan to pull a bank heist in a small town only to be smothered to distraction by the kindness of the locals. Critical reception was weak.