After two years army service, ending in 1958, he returned to the Playhouse at Meisner’s invitation to become his assistant. In 1960, John Frankenheimer, a friend of Pollack, asked him to come to Los Angeles in order to work as a dialogue coach for the child actors on Frankenheimer’s first big picture, The Young Savages. It was during this time that Pollack met Burt Lancaster who encouraged the young actor to try directing.

Pollack played a director in The Twilight Zone episode “The Trouble with Templeton” in 1961. But he found his real success in television in the 1960s by directing episodes of series, such as The Fugitive and The Alfred Hitchcock Hour. After doing TV he made the jump into film with a string of movies that drew public attention. His film-directing debut was The Slender Thread (1965). Over time, Pollack’s films received a total of 48 Academy Award nominations, winning 11 Oscars. His first Oscar nomination was for his 1969 film They Shoot Horses, Don’t They?, and his second in 1982 for Tootsie. For his 1985 film Out of Africa starring Meryl Streep and Robert Redford, Pollack won Academy Awards for directing and producing.

In the 2002 Sight & Sound Directors’ Poll, Pollack revealed his top ten films in alphabetical order:

Pollack received the first annual Extraordinary Contribution to Filmmaking award from the Austin Film Festival on October 21, 2006. As a producer he helped to guide many films that were successful with both critics and movie audiences, such as The Fabulous Baker Boys, The Talented Mr. Ripley, and Michael Clayton, a film in which he also starred opposite George Clooney and for which he received his sixth Academy Award nomination, in the Best Picture category. He formed a production company called Mirage Enterprises with the English director Anthony Minghella. The last film they produced together, The Reader, earned them both posthumous Oscar nominations for Best Picture. Besides his many feature film laurels, Pollack was nominated for five Primetime Emmys, earning two: one for directing in 1966 and another for producing, which was given four months after his death in 2008.

Concerns about Pollack’s health surfaced in 2007, when he withdrew from directing HBO’s television film Recount, which aired on May 25, 2008. Pollack died the next day at his home in Los Angeles surrounded by his family who confirmed that cancer was the cause of death but declined to provide specifics. His body was cremated, and his ashes were scattered along the runway at the Van Nuys Airport in Los Angeles.

One of a select group of non- and/or former actors awarded membership in the Actors Studio, Pollack resumed acting in the 1990s with appearances in such films as The Player (1992) and Eyes Wide Shut (1999), often playing corrupt or morally conflicted power figures. As a character actor, Pollack appeared in films such as A Civil Action, and Changing Lanes, as well as his own, including Random Hearts and The Interpreter (the latter also being his final film as a director). He also appeared in Woody Allen’s Husbands and Wives as a New York lawyer undergoing a midlife crisis, and in Robert Zemeckis’s Death Becomes Her as an emergency room doctor. His last role was as Patrick Dempsey’s father in the 2008 romantic comedy Made of Honor, which was playing in theaters at the time of his death. He was a recurring guest star on the NBC sitcom Will & Grace, playing Will Truman’s (Eric McCormack) unfaithful but loving father, George Truman. In addition to earlier appearances on NBC’s Just Shoot Me and Mad About You, in 2007, Pollack made guest appearances on the HBO TV series The Sopranos and Entourage.

Pollack was married to Claire Bradley Griswold, a former student of his, from 1958 until his death in 2008. They had three children: Steven (1959–1993), Rebecca (b. 1963), and Rachel (b. 1969). In November 1993, Steven died at the age of 34 in the crash of a small, single-engine plane which clipped a power line and burst into flames in Santa Monica, California. Claire, Pollack’s wife, died on March 28, 2011 at 74 years of age, due to Parkinson’s disease.