From the 1940s until 2001, the Sour Apple Award was presented by the Hollywood Women's Press Club to recognize male and female entertainers who exhibited rude or difficult behavior on set. Many of the most notoriously difficult celebrities to work with were granted this dubious honor, including actors Sean Penn, Ryan O'Neal, Joan Rivers, and Bruce Willis. Classic film stars Doris Day and Frank Sinatra were even awarded the Golden Apple Sour Apple three times each! For more tales of people who are hard to work with, check out Ranker's list of the most difficult actors.
1964, 1962, 1954
Olivia de Havilland