Angelina Jolie's 20 Hottest Moments

Angelina Jolies 20 Hottest Moments

Whether dazzling audiences with her breathtaking breakout in 'Gia,' assuming her rightful place as "Sexiest Woman Alive" on Esquire's November 2004 cover or walking the red carpet with Brad Pitt, Angelina Jolie never ceases to awe with her beauty. In a pictorial homage to the 'Changeling' star, Moviefone looks back at 20 of Angie's most jaw-dropping, eye-defying, downright sexiest moments ever. -- By Tom DiChiara

EW / Paramount / Esquire / WB

The Big Break

Though she'd already won a Golden Globe for the 1997 TV movie 'George Wallace,' it was Jolie's fearless turn as Gia Carangi -- a troubled supermodel with a penchant for drugs and showering with other women -- in HBO's 1998 biopic 'Gia,' that shot her to stardom. Looking at this photo, it's not hard to see why.

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Her Honor

'Gia,' earned Jolie her second Golden Globe win, a victory she celebrated by jumping into the pool at the Beverly Hilton Hotel while at a post-Globes party AND whilst still wearing her very expensive, extremely sexy Randolph Duke gown. "What's funny to me is that everyone wasn't jumping into the pool," Jolie would later tell Playboy. We agree.

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Cover Girl

Named to Rolling Stone's 1999 "Hot List," Angelina graciously accepted the honor by appearing in a super sultry, lingerie-clad photo on the cover of the magazine's Aug. 19, 1999, issue.

Rolling Stone Magazine

Statuesque Beauty

When Jolie won a Best Supporting Actress Academy Award in 2000 for her turn as a mental patient in 'Girl, Interrupted,' she made men everywhere insane with jealousy when she celebrated her victory by planting a kiss on a little golden man named Oscar.

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Brotherly Love

That same night, Jolie stirred up controversy, confusion and plenty of "brotherly love" jokes (see above) -- and strangely still made men everywhere jealous -- by bestowing a way-too-hot kiss on her peroxide-haired sibling, James Haven.

Gary Boas, Retna

The Butt-Kicking Babe

Jolie scored her first big box office hit ($131 million) when she tackled the title role in the 2001 adaptation of the popular video game, 'Lara Croft: Tomb Raider.' Fun fact: Jolie performed 80 percent of her own stunts in the action flick -- and still managed to look 100 percent sexy.

Paramount Pictures / Zuma Press

Blood and Lust

In what has to rank as one of the sexiest mag covers of all time, Angie graced Entertainment Weekly's June 15, 2001, issue wearing nothing but her birthday suit, a pair of earrings and a vial of then husband Billy Bob Thornton's blood around her neck. She sure knows how to accessorize.

Read EW's 2001 Angie cover story

ENTERTAINMENT WEEKLY used by permission of Entertainment Weekly Inc.

Provocative Ink

If ever there were a photo that made lying in the grass and staring up at the sky look like the best pastime imaginable, it's the July 5, 2001, cover of Rolling Stone. Never has a "Billy Bob" tattoo looked so sexy (or sexy at all, for that matter).

Rolling Stone Magazine

The Face of 'Tomorrow'

Even when Jolie plays down the sexiness, it shines right through. Exhibit A: this photo from 2004's 'Sky Captain and the World of Tomorrow,' a visually stunning fantasy flick in which Angie played a dry-humored, eye-patch-sporting badass named Franky. Admit it: You dig the eye patch.

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