She has crooned, campaigned, and crammed — and built a formidable career along the way

The Man in the Moon
1991 Witherspoon launched her career at 14 with her touching performance as a girl falling in love for the first time. $2.9 mil*

1996 Her turn as a troubled teenager in this edgy crime thriller showed off the actress’ range. $0.3 mil

1998 Witherspoon drew raves for this film in which she’s transported into a 1950s TV sitcom. $40.6 mil

Cruel Intentions
1999 The trashy-fun teen twist on Dangerous Liaisons paired Witherspoon with future husband Ryan Phillippe. $38.3 mil

1999 Witherspoon received a Golden Globe nod for her instantly iconic turn as overachiever Tracy Flick. $14.9 mil

Legally Blonde
2001 Witherspoon vaulted onto the A list with this comedy about a sorority girl who goes to Harvard Law School. $96.5 mil

Sweet Home Alabama
2002 The romantic-comedy smash returned the Nashville-raised Witherspoon to her Southern roots. $127.2 mil

Walk the Line
2005 Witherspoon’s performance as June Carter Cash earned her a Best Actress Oscar. $119.5 mil

Four Christmases
2008 Despite mixed reviews, this holiday comedy proved a success, demonstrating Witherspoon’s drawing power. $120.1 mil

Monsters vs. Aliens
2009 Witherspoon scored her biggest box office hit voicing a woman turned into a giantess by a meteorite. $198.4 mil