As Charlie Chaplin's third son, Sydney struggled to step out of his father's shadow. He had only limited success on film (appearing in two of his father's) but found greater fame onstage. He gained a reputation of being able to hold his own opposite powerhouse leading ladies. He won the Tony as Best Featured Actor in a Musical for his performance in Bells Are Ringing, opposite Judy Holliday:(Chaplin is in the middle, flanked by Holliday and Jerome Robbins)
He avoided getting mowed down by Barbra Streisand in her starring vehicle Funny Girl, winning a Tony nomination for Best Actor in a Musical for his portrayal of Nick Arnstein:Chaplin was not seriously considered to appear in his shows' film versions; his roles went to established movie stars. Dean Martin played his character in Bells Are Ringing, and Omar Sharif played Arnstein in Funny Girl (with most of the character's singing requirements removed). After several subsequent Broadway flops and some forgettable European movies, Chaplin retired to California and opened a restaurant. He died this week at the age of 82, leaving behind a son, a grand-daughter and, thanks to his father's four marriages, eight half-siblings, including actress Geraldine Chaplin.