He continued to direct a film a year throughout the 1960s and while he was liked, Pollack didn’t really break through commercially or critically until 1969’s They Shoot Horses Don’t They. That Jane Fonda starring Depression-era roller-dance epic was nominated for 9 Academy Awards and firmly established Pollack as one of the counter-culture filmmakers of the 1970s, whose politically active films changed Hollywood (other members in this illustrious club include Martin Scorsese, Francis Ford Coppola, and Peter Bogdanovich). Throughout the 1970s he made a variety of big budget productions, collaborating 4 times with star Robert Redford on such fondly remembered titles as Jeremiah Johnson, The Way We Were, Three Days Of The Condor, and The Electric Horseman. In addition to his star vehicles, Pollack also found the time to direct smaller cult oddities including the unfairly underrated 1974 Japanese gangster movie The Yakuza (which was the first screenplay by then-unknown writer Paul Schrader).

While his career took off the 1970s, Pollack’s breakthrough hit didn’t come until 1982 when he released his only comedy, the cross-dressing classic Tootsie. The film earned Jessica Lange an Academy Award and picked up 10 other nominations including best director. Tootsie was also an important movie for Pollack because it saw him return to acting for the first time in years. Dustin Hoffman was convinced that Pollack was the only man who could play his character’s agent and eventually persuaded Sydney to step out from behind the camera by sending him flowers with notes like “Please be my agent, love Dorothy.” Tootsie became the second highest grossing movie of 1982 after E.T., confirming Pollack’s status as a major Hollywood player.