Director Joan Micklin Silver cast the youthful Heard in "Between the Lines" (1977), a highly engaging story about the staff of a Boston underground paper dreading their impending sale to a print magnate. His association with Micklin Silver continued, with "On The Yard" (1978), when Heard was cast as a convict, and "Head Over Heels/Chilly Scenes of Winter" (1979), where he played an obsessed lover. Coveted parts followed: beat icon Jack Kerouac in "Heart Beat" (1979), a boozy angry Vietnam vet in "Cutter's Way" (1981), a mysterious zoo curator in Paul Schrader's remake of "Cat People" (1982), the seemingly helpful bartender who befriends Griffin Dunne in Martin Scorsese's "After Hours" (1985), and the unsympathetic son in Horton Foote's "The Trip To Bountiful" (1986).
In the late 1980s, Heard lightened up in such comedies as "Big", playing Tom Hanks' bullyish rival at the toy company, and "Beaches" (both 1988), as director of an avant garde theater company. But it was the unflappable buttoned-down father in "Home Alone" (1990) and it's sequel "Home Alone 2: Lost in New York" (1992) that moved Heard into blockbuster territory. He also turned in memorable performances in other hits, including "Awakenings" (1990), and Martha Coolidge's poignant coming of age comedy-drama "Rambling Rose" (1991). Heard has continued to work in features, turning in small but pivotal performances in "The Pelican Brief" and "In the Line of Fire" (both 1993), "My Fellow American" (1996), "Snake Eyes" (1998), "Pollock" (2000), "Animal Factory" (2000), "White Chicks" (2004) and dozens of other films. He assumed the Tommy Lee Jones role of Roy Foltrigg in the TV series adaptation of "John Grisham's 'The Client'" (CBS, 1995-96). He was especially effective in the recurring role of the corrupt police detective Vin Makazian, kept in the pocket of mob boss Tony Soprano, in the 1999 season of "The Sopranos" and was amusing as ABC executive Roone Arledge in the telepic "Monday Night Mayhem" (2002). He had a recurring role on "CSI: Miami" as Duke Duquesne and appeared in several episodes of the various "Law & Order" incarnations.