Cliff Robertson, best known to modern audiences for playing Peter Parker’s beloved Uncle Ben in the first three Spider-Man films and a film and television acting career that spanned more than six decades, died on Saturday of natural causes at New York’s Stony Brook University Medical Center one day after celebrating his 88th birthday.

Throughout his long and storied acting career Robertson has played a variety of authority figures and real-life influential personalities. He’s played astronaut Buzz Aldrin, automobile pioneer Henry Ford, and 19th century outlaw Cole Younger. Most notably Robertson played John F. Kennedy in the 1963 film PT 109, which documented the future President’s heroic leadership as a lieutenant in the U.S. Navy during World War II. Twenty years later, Robertson portrayed Playboy magazine founder Hugh Hefner in Star 80, the Bob Fosse-directed film about the shocking murder of Playboy playmate Dorothy Stratten. He played a devoutly religious U.S. President squaring off against Kurt Russell’s iconic badass antihero Snake Plissken in John Carpenter’s Escape from L.A. and in 1976 played the lead role in Brian DePalma’s psychological thriller Obsession.