10 best Oscar dresses of all time

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6. Hilary Swank

Perhaps one of the biggest sins of all time is that Hilary Swank’s career has been confined to a series of Jeopardy! questions and “where are they now?” trivia. While she’s currently got three films in the can, she hasn’t been seen much since 2007’s disastrous P.S. I Love You. But for a time, Hilary Swank was the toast of Hollywood, and she earned her stature by starring in quirky, driven movies that gave her an opportunity to play complex characters.

One of her Oscar winning roles – for Million Dollar Baby – occasioned her the opportunity to make the list of the 10 best Oscar dresses of all time. The year was 2005, and Hilary was walking down the carpet with her then-husband, Chad Lowe. She wore a floor length, royal blue Guy Laroche piece that was both backless and complimented her flawless derriere. All of her hard training for the role that would earn her one of her last Oscars was flaunted, shamelessly, in this dress, and we loved every minute of it – and of her. We can only hope that we’ll be seeing more of this in the future from Hilary Swank, who is one of the most talented actresses in Hollywood.