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Robertson played a future President of the United States in PT 109 (chosen personally by John F. Kennedy to portray the then-Lt. Kennedy) and a presidential candidate in The Best Man (1964). Later came Charly (an adaptation of Flowers for Algernon for which he won the 1968 Academy Award for Best Actor).
Other films included Picnic (1955), Autumn Leaves (1956), Gidget (1959), Sunday in New York (1963), Devil's Brigade (1968), Too Late the Hero (1970), J. W. Coop (1972), Three Days of the Condor (1975), Obsession (1976), Star 80 (1983) and Malone (1987). Late in his life Robertson's career had a resurgence. He appeared as Uncle Ben Parker in the first movie adaptation of Spider-Man (2002), as well as in the sequels Spider-Man 2 (2004) and Spider-Man 3 (2007). He commented on his website that "Since Spider-Man 1 and 2, I seem to have a whole new generation of fans. That in itself is a fine residual."[9] He was also in the horror film Riding the Bullet (2004).
Robertson's television appearances included The Twilight Zone episodes "A Hundred Yards Over the Rim" (1961) and "The Dummy" (1962) followed by guest starring roles in such series as the NBC medical drama about psychiatry The Eleventh Hour (1963) in the role of Jeff Dillon, "The Man Who Came Home Late". In 1958, he portrayed Joe Clay in the very first broadcast of Playhouse 90's Days of Wine and Roses, in what some critics cite as the superior version of this story about alcoholism. Other network appearances included The Greatest Show on Earth (1963) and ABC's Breaking Point (1964) and the ABC Stage 67 episode "The Trap of Gold" (1966).
He had a starring role in the live space opera Rod Brown of the Rocket Rangers (1953–1954), as well as recurring roles on Hallmark Hall of Fame (1952), Alcoa Theatre (1959), and Playhouse 90 (1958, 1960), The Outlaws (three episodes as Chad Burns), Batman as the villainous gunfighter Shame (1966, 1968), Falcon Crest (1983–1984) as Dr. Michael Ranson, and The Lyon's Den (2003). He had starring roles in episodes of both the 1960s and 1990s versions of The Outer Limits. He was awarded an Emmy for his leading role in an 1965 episode from Bob Hope Presents the Chrysler Theatre entitled "The Game". His second appearance on Batman featured his wife, Dina Merrill.
Robertson's most recent role(s) was that of Ben Parker in the Spiderman films.
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On September 10, 2011, Robertson died from natural causes in New York one day after his 88th birthday.
One of Robertson's main hobbies was flying. He was airborne and piloting a private Beechcraft Baron directly over New York City on the morning of September 11, 2001. He was directly over the World Trade Center, climbing through 7,500 feet, when the first Boeing 767 struck. He was ordered by air traffic control to land immediately at the nearest airport following a nationwide order to ground all civilian and commercial aircraft following the attacks.