Peter O'Toole
Twice.
No, not yet. But he has been nominated twice.
Kate Winslet
James Dean
Cate Blanchett as Queen Elizabeth
The Fresh Prince is also known has Will Smith. He has been nominated twice for the Academy Award.Nominated Oscar Best Actor in a Leading Role for: The Pursuit of Happyness (2006)Nominated Oscar Best Actor in a Leading Role for: Ali(2001)
He has been nominated twice for Best Actor for Saturday Night Fever (1977) and Pulp Fiction (1994).
James Dean
Twice. He was nominated for Best Supporting Actor in "The Talented Mr. Ripley" (1999) and for Best Actor in "Cold Mountain" (2003).
Grant was nominated twice for an Oscar{R} and five times for a Golden Globe, but never won. He was awarded an honorary Oscar{R} in 1970.
Twice. She won the 1997 Best Actress award for her performance in "As Good As It Gets." She was nominated for Best Supporting Actress for her work in the 2012 drama "The Sessions."
Leonardo DiCaprio has never won the Academy Award (Oscar) for Best Supporting Actor. He was nominated for this award for his role in What's Eating Gilbert Grape (1993). He has also been nominated for the Oscar for Best Actor twice, but he has not won yet.