More teen-oriented projects ("Where the Boys Are '84" and "Breakin'", both 1984) followed, but McDonald managed to work in a stay in London where he studied for eighteen months. Upon his return to L.A., guest spots on TV came along, as did a number of movies on the small and big screens, among them the feature comedies "Chattanooga Choo Choo" (1984) and "Outrageous Fortune" (1987). McDonald assumed a higher profile in "Chances Are" (1989), as Cybill Shepherd's husband, who dies and comes back as Robert Downey Jr, before "Thelma & Louise" really thrust him in the public eye. He had a recurring part as Nick (the husband of Park Overall's character) in NBC's "Empty Nest" (four episodes from 1989-92) and regular roles on the short-lived series "Call to Glory" (ABC, 1984-85) and "Walter and Emily" (NBC, 1991-92). He also portrayed Tasha Yar's (Denise Crosby) love interest Richard Castillo in "Yesterday's Enterprise", an extremely popular episode of "Star Trek: The Next Generation", and acted in two USA Network movies, "Red Wind" (1991) and "Fatal Exposure" (1991).
Though the demand for him in features increased exponentially after "Thelma & Louise", McDonald chose to make many forgettable movies, but he was especially fine in Robert Redford's "Quiz Show" (1994) as Jack Barry, the host of the rigged 50s game show "21", and followed with his first action film, playing an extremely nasty Russian mobster in "Terminal Velocity" (1994). McDonald acted in five features released in 1996, checking out early once again as the murdered husband of Halle Berry in "The Rich Man's Wife", and probably received his biggest exposure and best notices that year for his well-rounded performance in "Happy Gilmore", playing Adam Sandler's jock nemesis. He should probably have avoided his turn as Ward Cleaver in the dreadful "Leave It to Beaver", likewise his role in "A Smile Like Yours" (both 1997), but faired better with the independent "Lawn Dogs" and the remake "Flubber" (both 1997), starring Robin Williams. Despite his busy feature schedule, McDonald managed to take on a recurring role as the philandering husband of Kirstie Alley's designer in NBC's highly-touted sitcom "Veronica's Closet".