One of the first generation of feature filmmakers who learned their craft directing for television – a generation that included William Friedkin, Robert Altman, Sidney Lumet and John Frankenheimer  – writer-producer-director Sydney Pollack forged a wide-ranging career that leaned heavily towards grown up, character-driven dramas while tossing in the occasional comedy curveballs, like the gender-bending hit Tootsie (1982). Pollack's work earned him two Oscars – both for Out of Africa (1985) – and nominations for five more, including a nod for his role in producing The Reader (2008), one of his last films. Born in Lafayette, Indiana, in 1934 and raised in South Bend, Pollack's father was a pharmacist who once boxed professionally; his mother was a homemaker who died when he was a teenager.  Pollack fell in love with drama at South Bend High School and, despite his father's disapproval, opted to forgo college in favor of moving to New York City and trying to become a professional actor. He studied under the renowned Sandford Meisner at the Neighborhood Playhouse School of the Theater and quickly earned roles in such Broadway productions as A Stone for Danny Fisher, with Zero Mostel, and The Dark Is Light Enough, starring legendary stage actress Katharine Cornell. He also made more than a dozen episodic television appearances, notably in the two-part Playhouse 90 production of For Whom the Bell Tolls (1959); the stellar cast included Maureen Stapleton, Eli Wallach, Jason Robards, Maria Schell, Nehemiah Persoff and legendary acting teacher Herbert Berghof, under the direction of Frankenheimer, who was only four years Pollack's senior. By the early 1960s, Pollack's agent -- powerhouse Lew Wasserman -- also secured some directing gigs for his young client Encouraged by Hollywood legend Burt Lancaster, whom he met through Frankenheimer, Pollack redirected his ambition behind the camera and didn't act again until 1982, with the exception of a brief, unbilled bit in his own The Electric Horseman (1979). But Pollack's return to acting was showstopper: He played Dustin Hoffman's exasperated agent in Tootsie, and if he didn't quite steal the show from his temperamental star – the two feuded throughout production -- he gave him a run for his money – this despite the fact that he was uncredited. Until his death, Pollack alternated between acting and directing, sometimes doing both, and left his mark on a generation television viewers playing the recurring role of Will's philandering father on Will & Grace. His last film roles were as George Clooney's boss and Patrick Dempsey's father in, respectively, Michael Clayton (2007) and Made of Honor (2008). Pollack was know for his skill at directing actors, which he attributed to his own experience as a performer. Over the course of a directing career that spanned five decades, Pollack directed 20 films, including critical and box office successes like They Shoot Horses, Don't They? (1969), The Way We Were (1973), Jeremiah Johnson (1972), Three Days of the Condor (1975) and The Firm (1993). Interspersed among the hits were some spectacular misses: The Harrison Ford-Julia Ormond remake of Sabrina (1995); Bobby Deerfield (1977), with Al Pacino; and the notorious Havana (1990), with Raul Julia, Lena Olin and Pollack's frequent collaborator, Robert Redford. Redford and Pollack eventually made seven films together, starting with This Property is Condemned (1966), becoming close friends in the process. He also worked on several films with his brother, Bernie Pollack, a costume designer whose credits include Indiana Jones and the Kingdom of the Crystal Skull (2008). Their sister, Sharon, became a dance teacher. Pollack and his wife, actress Claire Griswold, were married in 1958, and had three children. One  daughter, Rebecca Pollack-Parker, was a production executive at United Artists during the 1990s; the other, Rachel Pollack-Sorman, is a singer. Their son, Steven Pollack, died in a single-engine plane crash in 1993.