Just came across these Rolling Stone outtakes. They're 32D in case anyone was wondering (confirmed by her "Beetlejuice, Beetlejuice" Costume Designer.)
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and a bonus -
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Merry Xmas!
Ty so much, never seen that halter top one
I often think of this interview by Daniel Waters, who wrote Heathers & later made Sex & Death 101, one of Winona's VERY rare topless scenes: "I kept a very relaxed and studiously unserious set, but even I was a little shocked when Winona insisted on rehearsing her love scene topless, who was I to protest. Unfortunately we were using two cameras so the set was not as closed as it should have been (Am I imagining two boom operators). Winona was classically undisturbed, making Mrs. Roper-like cracks about how she hadn't been on a date for 11 months. Laughing at the wit of a beautiful, charming, and unclothed actress, while maintaining eye contact is something they don't teach you on Project Greenlight. I thought I was going to have to pass out neck braces to the crew."
DEFINITELY wish she had more nudity on her resume, she fucked half the grunge rockers in the 90s but sadly kept a lid on it on screen mostly, the nipples in Sex & Death & Autumn in New York are very fleeting in the final films - I'll be dreaming of the Xmas gift of her MILF Demi Moore Substance comeback...