The crossword solutions for the term TOOTSIE OSCAR WINNER JESSICA are LANGE. Jessica Lange is an American actress who won the Academy Award for Best Supporting Actress for her role as Dorothy Michaels in the 1982 comedy-drama film Tootsie. She has also won two Emmy Awards, four Golden Globe Awards, one Screen Actors Guild Award, and three Dorian Awards. Lange is one of the most acclaimed actresses of her generation and has received numerous accolades throughout her career.