Reese Witherspoon

While still in high school, Witherspoon completed two more feature films, Jack the Bear (1993), starring Danny De Vito, and Disney's A Far Off Place (1993), which required the actress to spend several months living in the Kalahari Desert. Following a supporting role in the 1993 CBS miniseries Return to Lonesome Dove and a lead in the critically disembowelled S.F.W., Witherspoon temporarily set aside her career to study English literature at Stanford University. She then returned to film as the abused girlfriend of a psychotic Mark Wahlberg in the thriller Fear (1996). In the same year, she had to deal with yet another crazed male in Freeway, a satirical version of -Little Red Riding Hood in which Witherspoon co-starred with Kiefer Sutherland, who took on the role of the aforementioned crazed male.

Her career began to take off in 1998, with roles in two high-profile films. The first, Twilight, saw her sharing the screen with Gene Hackman, Susan Sarandon, and Paul Newman. The film received mixed reviews and lackluster box office, but Pleasantville, her other project that year, proved to be both a critical and financial hit. The actress won wide recognition for her leading role as Tobey Maguire's oversexed sister, and this recognition -- along with critical respect -- increased the following year with another leading role, in Alexander Payne's acclaimed satire Election. Starring opposite Matthew Broderick, Witherspoon won raves for her hilarious, high-strung portrayal of student-council presidential candidate Tracy Flick. The character stood in stark contrast to the one Witherspoon subsequently portrayed in Cruel Intentions, Roger Kumble's delightfully trashy all-teen update of Dangerous Liaisons. As the virginal Annette, Witherspoon was convincing as the object of Ryan Phillippe's reluctant affection, perhaps due in part to her real-life relationship with the actor, whom she married in June 1999.

After turning up in an amusing minor role as serial killer Patrick Bateman's burnt-out yuppie girlfriend in American Psycho (2000), Witherspoon again pleased critics and audiences alike with her decidedly Clueless-esque role in 2001's Legally Blonde. Her star turn as a seemingly dimwitted sorority blonde-turned-Harvard law-school-prodigy unexpectedly shot the featherweight comedy to number one, despite such heavy summer contenders as Steven Spielberg's A.I. and the ominously cast heist thriller The Score. The 18-million-dollar film went on to gross nearly 100 million dollars, proving that Witherspoon had finally arrived as a box-office draw.

Though she would test out her chops in the Oscar Wilde adaptation The Importance of Being Earnest, Witherspoon's proper follow-up to Legally Blonde came in the form of 2002's Sweet Home Alabama, a culture-clash romantic comedy as embraced by audiences as it was rejected by critics. As with Drew Barrymore before her, Witherspoon used her newfound standing among the Hollywood elite to start her own production company, Type A Films, as well as to up her asking price to the rarefied 15-million-dollar range for the sequel to Legally Blonde. Though Blonde 2 didn't perform quite as well as the first film, the power player/doting mother of two wasted no time in prepping other projects for the screen, taking the lead in 2004's elaborate costume drama Vanity Fair as Becky Sharp, a woman who strives to transcend class barriers in 19th century England. For all its lavish costumes and sets, Vanity Fair received mixed reviews, but Witherspoon's winning performance still garnered praise.

The next year, she appeared in the heaven-can-wait romantic comedy Just Like Heaven with Mark Ruffalo, as well as James Mangold's biopic Walk the Line as June Carter Cash, wife of country music legend Johnny Cash. This role proved to be a pivotal one, earning Witherspoon both a Best Actress Academy Award and a Golden Globe for her performance, and cementing her as an actress whose abilities go far beyond her charm and pretty face.

As with others before her, however, the Best Actress statue portended a breakup between her and her husband; in October, 2006, she and Phillippe began their divorce proceedings, shortly after his starring turn in Clint Eastwood's Flags of Our Fathers. ~ Rebecca Flint Marx