As of 2008, she is only one of six actors who have a 2-0 winning record when nominated for an acting Oscar. The others are Luise Rainer for The Great Ziegfeld (1936) and The Good Earth (1937); Vivien Leigh for Gone with the Wind (1939) and A Streetcar Named Desire (1951); Helen Hayes for The Sin of Madelon Claudet (1931) and Airport (1970); Sally Field for Norma Rae (1979) and Places in the Heart (1984); and Kevin Spacey for The Usual Suspects (1995) and American Beauty (1999).
Hilary's 20th birthday party was a 1974 themed party and was held in Hollywood at The Crush Bar.
Made her film debut in Buffy the Vampire Slayer (1992).
Met her ex-husband Chad Lowe on set of Quiet Days in Hollywood (1995), married after 5-month relationship.
Auditioned for the role of Lucy Hatcher on the television series "The Practice" (1997).
She won the lead role of Brandon/Teena in Boys Don't Cry (1999) after hundreds of other actresses had been considered and rejected over the course of three years. Told director Kimberly Peirce that, like her character, she was also 21 and hailed from Lincoln, Nebraska. But she was fibbing, and when Peirce later confronted her with the lies, she winningly responded: "But that's what Brandon would do."
For a few weeks before Boys Don't Cry (1999) began filming, she went out in public dressed as a boy. Many were fooled by the disguise.
Was declared #6 on the show "Hollywood's Ten Best Beauty to Beast" transformations for the way she looked in Boys Don't Cry (1999). Three other actresses on the list were nominated for Oscars for their movies and two won: Charlize Theron (Monster (2003)), Halle Berry (Monster's Ball (2001)) and Salma Hayek (Frida (2002)).
Cut off all of her hair and lived as a boy for a month to prepare her for her role as Teena Brandon in Boys Don't Cry (1999).
Earned $75 a day for Boys Don't Cry (1999).
Awarded an Emery Award for her role in Boys Don't Cry (1999) (November 2006).
Her performance as "Brandon Teena" in Boys Don't Cry (1999) is ranked #83 on Premiere Magazine's 100 Greatest Performances of All Time (2006).
Named one of "People" magazine's 50 Most Beautiful People in 2000, 2004 and 2005.
Was in consideration for the part of Satine in Moulin Rouge! (2001) but Nicole Kidman, who went on to receive a Best Actress Oscar nomination for her performance, was cast instead.
She and husband moved into a 4-story brownstone home in Greenwich Village (NYC) they bought for $4 million. (June, 2002)
Replaced Sandra Bullock as "Maggie Fitzgerald" in Million Dollar Baby (2004) after Bullock dropped out for other commitments.
Although she was naturally athletic from high school, she totally changed physically to play Maggie in Million Dollar Baby (2004). She gained nearly 20 pounds, becoming so buff that her former clothes are still too small for her.
Fined NZ$200 (AUD$190) for bringing undeclared fruit into New Zealand. She was found with an apple and orange at New Zealand's Auckland International Airport. She has since contested the fine (15 January 2005).
Her longtime companion has been her agent John Campisi since December 2006.
Announced in January 2006 that she and her husband Chad Lowe are separating after 8 years of marriage.
Was listed as a potential nominee on the 2008 Razzie Award nominating ballot. She was suggested in the Worst Actress category for her performances in the films P.S. I Love You (2007) and The Reaping (2007). She failed to receive a nomination however.
Received a cut on the forehead during filming a scene of her movie P.S. I Love You (2007). She had to be brought to a hospital and received several stitches (November 2006).
Received the 2,325th star on the Hollywood Walk of Fame (8 January 2007).
Was originally cast as Rachel in Something Borrowed (2011) but after dropping out of the project Ginnifer Goodwin was cast instead.