During the mid-1990s, Samantha Smith enjoyed frequent guest star appearances on television shows, which she was able to parlay into film roles. Along with providing laughs on episodes of the hit comedies "Seinfeld" and "Wings", her early roles included an appearance on a "Caroline in the City" two-parter. Meanwhile, her first movie appearance came in the blockbuster romantic comedy "Jerry Maguire" starring Tom Cruise, in which she played a former girlfriend of the title character. Toward the end of the '90s, she landed a guest part on "Friends", arguably the most popular comedy on television, as well as a recurring role on the procedural drama "Profiler" as Kate Wilton. The 2000s brought a combination of recurring roles, guest-star appearances, and stray movie parts, including screen time as a flight attendant in "What Planet Are You From?", a Mike Nichols comedy film starring Garry Shandling. She had another nameless part in the '02 movie thriller "Dragonfly" with Kevin Costner, but that trend ended with the '07 action blockbuster "Transformers", in which she played Sarah Lennox, the loving wife of Josh Duhamel's Captain William Lennox. Smith's career also got a boost around this time by a recurring part in "Supernatural", a television action-drama about demon-hunting brothers. As Mary Winchester, the siblings' ill-fated mother, she appeared in the show's pilot as well as several more episodes from '05 onward.