He was seen in the film "The Milagro Beanfield War" and had a significant role playing Paul, Tom Hanks's adult corporate competitor and jilted boyfriend of Elizabeth Perkins, in "Big" (both 1988). He co-starred with Bette Midler in "Beaches" (also 1988). In 1990 Heard starred in the philosophical film "Mindwalk", in which three characters from different socialitical and poetical backgrounds express their opinions on the human experience, and around the same time, he was in "Awakenings" alongside Robert De Niro and Robin Williams, starred in "Deceived" (1991), with Goldie Hawn, playing Jack Saunders, and had a supporting role in "Gladiator" (1992), with Cuba Gooding Jr.