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.