How many times did an Oscar category feature five nominated actors or actresses who were past or future Oscar winners?
There have never been five past winners in a category. But there were a few times with past and future winners nominated together:
1967 Best Actor- future winners include Warren Beatty, who won for direction
1968 Best Actress
1973 Best Actor- future winners include Robert Redford, who won for direction
1985 Best Actress
1990 Best Actress
2001 Best Actress & Best Supporting Actress
2002 Best Actor (four past winnners, and the fifth nominee won)
2006 Best Actress
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