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Reese Witherspoon's 9 Best Roles

Reese Witherspoon
Getty Images

It can take several decades for the Oscars to recognize actors for their career accomplishments. But not the MTV Movie Awards.

At this weekend's Movie Awards, Reese Witherspoon will receive the coveted Generation Award for her 20-year career delighting moviegoers.

The MTV Generation Award is given to actors and actresses whose entire body of work has entertained, challenged and impressed audiences. Witherspoon joins the ranks of such previous winners as Jim Carrey, Adam Sandler and Sandra Bullock; at 35, she'll be the youngest star yet to receive the award.

In honor of this achievement, we've compiled Reese's nine greatest roles, from circus performer to overachieving high schooler to country music star.

9. 'Sweet Home Alabama' (2002)

Sweet Home Alabama
Touchstone

As Melanie Smooter, the big-city fashion designer who can't quite shake her small-town Southern roots, Reese Witherspoon charms her way into the hearts of viewers and two eligible onscreen suitors played by Josh Lucas and Patrick Dempsey. Whether she's drinking it up at the local bar, butting heads with her childhood sweetheart or punching out her would-be mother-in-law (Candice Bergen), she does so with girlish charm and an Alabama twang to back it up.

8. 'Water for Elephants' (2011)

Water for Elephants
20th Century Fox

Witherspoon shares the scren with Robert Pattinson in this year's adaptation of Sara Gruen's novel; but that isn't the reason this is one of her best roles (although it helps!). As star circus performer Marlena, Witherspoon possesses an otherworldly grace. And she jumps from moving trains! And performs beautiful, death-defying stunts with a stunning elephant named Rosie! And did we mention that she shares love scenes with a "Twilight" star? Right.

7. 'The Man in the Moon' (1991)

The Man in the Moon
MGM

Long before sharing the screen with "Twilight" heartthrobs, a 15-year-old Witherspoon starred as a 1950s teen whose heart is broken one Louisiana summer. Her character Dani is a headstrong tomboy whose first real crush is complicated by her sister's feelings for the same neighbor. The future Oscar winner's honest portrayal of the stubborn tween was a precursor to other likable but independent-minded characters to come in "Sweet Home Alabama," "Legally Blonde" and "Walk the Line."

6. 'American Psycho' (2000)

American Psycho
Universal

Oh, Evelyn Williams; shallow, unsuspecting yuppie girlfriend to Christian Bale's Patrick Bateman -- how we do love you. Before embarking on a murderous Manhattan rampage,Bateman may have broken her heart by declaring, "You're not terribly important to me," but to us and to Witherspoon's career, the role of Evelyn Williams was quite the opposite.

5. 'Pleasantville' (1998)

Pleasantville
New Line

For proof that Witherspoon's range extends into superficial (and scandalous) territory, look no further than "Pleasantville." As Mary Sue (née Jennifer), a modern-day teenager who inconveniently finds herself trapped inside a '50s sitcom, the actress torments innocent schoolboys with sex, harasses her geeky brother and discusses masturbation with her housewife mother. Oh, and she also lays this harsh wisdom on her 1950s counterparts: "Nobody's happy in a poodle skirt and a sweater set." She does have a point.

4. 'Cruel Intentions' (1999)

Cruel Intentions
Columbia Pictures

It was as Ryan Phillippe's virginal "Cruel Intentions" conquest that most MTV audiences first saw Witherspoon. The beautiful Annette Hargrove proved that true high school love can conquer all, including womanizing peers, spiteful step siblings and vintage Jaguars.

3. 'Election' (1999)

Election
Paramount

Is there anything more delicious than watching high school overachiever Tracy Flick slowly destroy the life of Mr. McAllister (Matthew Broderick)? The short answer is no. Whether she is naively ruining the marriage of a faculty member, terrorizing her opponent's campaign posters or just setting up a folding table with scary intensity, Tracy Flick is undeniably hilarious.

2. 'Legally Blonde' (2001)

Legally Blonde
MGM

No one does beauty and brains like Elle Woods. And perhaps no movie character ever will again, at least at Harvard, with a pint-size dog named Bruiser, a manicurist best friend and crucial, case-solving knowledge of perms. All hail one of the best female role models to rise from the cinema in the past 20 years.

1. 'Walk the Line' (2005)

Walk the Line
20th Century Fox

Even the Academy could not deny Witherspoon's brilliant portrayal of June Carter Cash. As one half of the greatest country-singing couples in history, Witherspoon sang beautifully and exhibited strength, charm and inspiration in her only biographical role on this list. Her performance in 'Walk the Line' will be difficult to top but we can't wait for the actress to keep trying.

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