- Auditioned for the movie A League of Their Own (1992) but didn't get the role because she couldn't play baseball well enough.
- Is the eldest of three children born to an advertising executive dad and a literary agent mom.
- Treated for addiction to prescription medication.
- Her mother is Charlotte Sheedy, a prominent New York literary agent.
- Dated Richie Sambora.
- Turned down the lead role in Wild Orchid (1990).
- Auditioned for the Molly Ringwald role in Sixteen Candles (1984).
- Dated Eric Stoltz for five years.
- Dated Woody Harrelson.
- Turned down the Kelly McGillis role in Top Gun (1986).
- The addiction treatment Sheedy received was for sleeping pills. This helped her choose to participate in the film High Art (1998), in which she played a once- famous photographer who had also descended into drug addiction.
- Was the first biological female to play the transgendered rock star Hedwig in the stage musical "Hedwig and the Angry Inch".
- Went to school with Lauren Marie Taylor, who starred in Friday The 13th II. They are still friends today.
- Was one of the nine original members of the 1980s "brat pack", along with Judd Nelson, Mare Winningham, Anthony Michael Hall, Demi Moore, Rob Lowe, Molly Ringwald, Emilio Estevez and Andrew McCarthy.
- Danced with the American Ballet Theatre from about the time she was six and was rapidly pursuing a career, but when puberty caused her breasts to fill out and all the starvation diets caused her an eating disorder, she gave up dance and pursued acting full-time.
- Wrote a best selling novel at the the tender age of 12.
- Became pregnant while filming Talia Shire`s "One Night Stand"
- Daughter Rebecca Elizabeth was born March 15,1994.
- Was a bridesmaid at Demi Moore's and Bruce Willis' wedding
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