In partnership with Robert Chartoff from the late 1960s, Irwin Winkler produced an impressive array of modern American gems, beginning with their first effort (along with Judd Bernard), John Boorman's taut thriller Point Blank (1967), largely ignored in its day but now regarded as a top film of the time. Adding Sydney Pollack to their production team for a one-shot-deal, they garnered critical acclaim for They Shoot Horses, Don't They? (1969). Their next film, The Strawberry Statement (1970), won the Jury Prize at Cannes but Chartoff and Winkler roared to the top with Rocky (1976), which earned the Academy Award as Best Picture. Subsequently, the producing duo picked up Best Picture Oscar nominations for Raging Bull (1980) and The Right Stuff (1983), their last project together before Winkler launched his solo career with the disappointing Revolution (1985).
Approaching the age of 60, Winkler moved into the director's chair, debuting with Guilty by Suspicion (1991), a drama (which he also scripted) about the Hollywood blacklist that starred Robert De Niro. His second feature, the unsuccessful 1992 remake of Night and the City, also starred De Niro. Winkler had better luck at the box office as writer-director of the Sandra Bullock vehicle The Net (1995), which spawned a series of the same name debuting on the USA Network in 1998, but got mired in syrupy sentimentality in At First Sight (1999) a gooey romance-drama starring Val Kilmer as a blind man whose bid to regain his sight complicates his relationship with his girlfriend (Mira Sorvino).
The director delivered one of his most potent films yet with Life as a House (2001), a complex, emotional and frequently amusing tale featuring a depressed dying man (Kevin Kline) who funnels his energies into rebuilding the dilapidated beach shack he inherited from his abusive father and, in the process, building bridges between himself and his disaffected son (Hayden Christensen). Receiving a healthy dose of critical praise, Winkler re-teamed with Kline for the follow-up De-Lovely (2004), casting the actor as the lead in his elegant and sophisticated biographical film of American composer Cole Porter centered on his unique relationship with his wife and muse (Ashley Judd).
As his directorial career flourished, Winkler continued to produce his share of films as well, including The Shipping News (2001) and Enough (2002).