Angelina Jolie: How She Earned Her Stripes
Best Geek Chic
Proving that computer nerds can be sexy, a Vulcan-coiffed Jolie made her feature film breakthrough — and made costar Jonny Lee Miller her first husband.
Best Bad Role Model
Starring as self-destructive '80s supermodel Gia Carangi in the HBO film, Jolie won her second straight Golden Globe for a TV movie (the first was for 1997's George Wallace).
Best Life-Imitates-Art Role
Pushing Tin (1999)
Before the brief marriage, tattoos, and vials of blood, Billy Bob Thornton and Jolie (shown with Cate Blanchett, left) met as costars, playing a quirky, intense air traffic controller and his lonely, oversexed wife.
Most Thankless Part
The Bone Collector (1999)
Cop Amelia Donaghy (Jolie) must serve as the eyes, ears, and legs of her quadriplegic partner, Lincoln Rhyme (Denzel Washington), as they track a serial killer.
Girl, Interrupted (1999)
Playing Lisa Rowe, a charismatic mental patient, Jolie stole the movie from star Winona Ryder, winning a Best Supporting Actress Oscar in the process.
Best Excuse For Playing A Videogame Heroine
Lara Croft: Tomb Raider (2001)
Talking to EW, Jolie described acrobatic archaeologist Croft as a privileged gal ''who does amazing things but is completely out of her mind in a really wicked way. She's a lot like me, actually.''
Original Sin (2001)
Despite the steamy coupling of Jolie and Antonio Banderas in this sudsy period piece about a wealthy Cuban landowner who marries a femme fatale, the movie took a bath at the box office.
Best Kinky Cameo
Sky Captain and the World of Tomorrow (2004)
As British officer Franky Cook, an ally and former flame of Joe ''Sky Captain'' Sullivan (Jude Law), Jolie proves she can make even an eye patch sexy.
Fishiest Femme Fatale
Shark Tale (2004)
Voicing a golddigging lion fish with familiar-looking lips, Jolie plays Lola (left), who flirts with newly-famous Oscar (right, voiced by Will Smith) while sweet angelfish Angie (Renée Zellweger) pines in the background.
Jolie, 29 at the time, played Olympias, mother to Alexander the Great, played by Colin Farrell, then 28. Maybe director Oliver Stone thought he was casting for another Greek drama: Oedipus Rex
Best Assassination Tango
Mr. and Mrs. Smith (2005)
Though director Doug Liman's film about a married pair of contract killers was a fun, stylish flick with some pretty decent action scenes, it'll probably be best remembered for bringing together — off screen, eventually — Jolie and Brad Pitt.
The Good Shepherd (2006)
In her small role as the frustrated wife of a CIA agent (Matt Damon), Jolie was ''lassoed in ladylike dresses and pearls,'' wrote EW critic Lisa Schwarzbaum.
Most Challenging Role
A Mighty Heart (2007)
''I don't think there was a day on set I was confident of what I was doing, but I knew my heart was in the right place,'' Jolie told EW about playing Mariane Pearl, the freelance journalist whose husband, Daniel, was kidnapped and ultimately beheaded, on camera, in Pakistan in '02. Besides the role's emotional challenges, Jolie also transformed her look and her accent during the fraught shoot in India.
Best Mother Of All Evil
Jolie has portrayed a mother (in Alexander) and a seductress (in almost everything else), but with Robert Zemeckis' totally CG film, she combined the two. As the demon who sired the hideous Grendel and bedded the egotistical Geat hero, Jolie played right into the image many have of her: irresistible.
Most Cuddly Martial Artist
Kung Fu Panda (2008)
As Tigress, she was the deadliest of the Furious Five — a quintet of kung-fu heroes trained to defeat the villainous Tai Lung (Ian McShane) — and the one you most wanted to hug.
Kung Fu Panda 2 (2011)
Her return as the steady, reliable, and supportive Tigress who helps Po find his family helped the sequel continue to rake in the dough.
Most Inexplicable Comedy
The Tourist (2010)
Jolie's turn as the mysterious Elise who meets up with Johnny Depp's seemingly hapless traveler earned her a Golden Globe nomination for Best Performance by an Actress in a Motion Picture - Musical or Comedy.
Best Double (Double) Agent
This post cold-war Soviet plot thriller worked in large part thanks to her frantic-then-calculating turn as CIA agent Evelyn Salt.
Sexiest Professional Assassin
With her mysterious ways and physics-defying ballistic moves, her Fox was one of the best things about this movie with a Loom of Fate at its core.
Most Stubborn Mother
She takes mother's intuition and love to a new level in this quiet Clint Eastwood-directed movie about a woman's search for her missing child.