milestones
Year
Milestone
 
Raised in Nashville, Tennessee
1983 
Began acting in local commercials at age seven
1991 
Film debut in "The Man in the Moon"; also marked first on-screen kiss
1991 
TV acting debut in Lifetime movie "Wildflower"; directed by Diane Keaton
1993 
First starring role, "A Far Off Place"
1993 
Co-starred in CBS miniseries "Return to Lonesome Dove"
1993 
Acted in Marshall Herskowitz's "Jack the Bear"
1995 
Starred as satirical mini-mart hostage who lets loose a bitchy side in "S.F.W."
1996 
Played a troubled, precocious girl with a dark past in "Freeway" (aired on HBO before its theatrical release)
1996 
Starred as the object of Mark Wahlberg's obsession in "Fear"
1998 
Played the daughter of Gene Hackman and Susan Sarandon in Robert Benton's "Twilight"
1998 
Transported back to the black-and-white world of 1950s television in Gary Ross' "Pleasantville"
1999 
Cast as a virginal teenager in "Cruel Intentions," a modern-day spin on "Les Liaisons Dangereuses"
1999 
Cast as Tracy Flick, a manipulative overachiever running for class president in Alexander Payne's "Election"
1999 
Starred alongside Alessandro Nivola and Josh Brolin in "Best Laid Plans"
2000 
Made two-episode appearance as the kid sister of Rachel (Jennifer Aniston) in the NBC sitcom "Friends"
2001 
Starred in the surprise hit comedy "Legally Blonde"
2002 
Played Cecily Cardew in a film remake of "The Importance of Being Earnest"
2002 
Starred as a Southern girl who remakes herself as a New York socialite in "Sweet Home Alabama"
2003 
Reprised the role of Elle Woods for "Legally Blonde 2: Red, White and Blond"
2004 
Starred in the period film "Vanity Fair" directed by Mira Nair
2005 
Co-starred opposite Joaquin Phoenix, as June Carter Cash in "Walk the Line"; a biopic of late country music legend Johnny Cash, directed by James Mangold
2006 
Witherspoon surpassed Hollywood superstar Julia Roberts to become the highest paid actress of all time; She will earn $29 million for the horror film "Our Family Trouble"
2007 
Played a pregnant Midwestern woman who discovers that her Egyptian husband is being secretly held by the U.S. government in "Rendition"
2008 
Producing debut (also co-starred), "Penelope" starring Christina Ricci in the title role (lensed 2006)
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