Drew Barrymore

Unsurprisingly, observers began writing Barrymore off as just another failed child star when she was barely into her teens. She made a string of (largely forgettable) movies, many of which only reinforced her image as a has-been. However, in the middle of her teen years, Barrymore entered rehab, cleaned herself up, and wrote an autobiography, Little Girl Lost, which detailed her travails with drugs and alcohol. In the early 1990s, she entered another phase in her career, gaining notoriety for playing a series of vampy, trampy trailer-park Lolitas. In this capacity, she turned in memorable performances in Poison Ivy (1992), the 1993 made-for-TV The Amy Fisher Story, and Batman Forever (1995), all of which featured her pouting seductively and showing more thigh than all the Rockettes combined. Barrymore's on-screen antics were ably complemented by the off-screen reputation she was forming at the time: first she could be seen posing nude with then-boyfriend Jamie Walters on the cover of Interview magazine, then modeling for a series of racy Guess ads, flashing David Letterman during an appearance on The Late Show as a "birthday present" to the host, and finally posing nude for Playboy in 1995.

In 1996, Barrymore's image underwent an abrupt and effective transformation from slut to sweetheart. With a brief but memorable role in Wes Craven's Scream and a lead in Woody Allen's Everyone Says I Love You that featured her as a Kelly Girl for the '90s, Barrymore's career received an adrenaline shot to the heart. She began working steadily again, and she reshaped her offscreen persona into that of a delightful and sweet-natured girl trying to mend her ways. This new image was supported by her screen work, much of which featured her as a chaste heroine. Her starring role as the "real" Cinderella in Ever After (1998) was a good example, and it had the added advantage of turning out to be a fairly solid hit. Barrymore's other major 1998 film, The Wedding Singer, was another hit, further enhancing her reputation as America's new sweetheart. The following year, the actress all but put the final nail in the coffin of her wild-child reputation of years past, starring as the nerdy, lovelorn twenty-something reporter who bears the titular condition of Never Been Kissed. That movie not only marked a notable transition in Barrymore's reputation, but an advancement in her cinematic career as well. Expanding her role from actress to producer, Barrymore would continue starring in and producing such efforts as Charlie's Angels (2000), Donnie Darko (2001).

Though some may have suspected that her millennial transition from sweetheart to skull-cracker in Charlie's Angels may have signaled a shift towards more action oriented roles -- and despite her return to the role in Charlie's Angels: Full Throttle (2003) -- Barrymore once again charmed audiences with another emotional comedy, Riding in Cars With Boys in 2001, while Confessions of a Dangerous Mind (2002) found Drew in the role of long-suffering girlfriend alongside Sam Rockwell's unlikely CIA operative. Though the film did not fare particularly well critically or otherwise, Barrymore took a nonetheless interesting turn as an apple-pie wife turned sinister in 2003's Duplex, and held her own against scene-chomper Ben Stiller. Barrymore teamed up with fellow Stiller-flick alumni Owen Wilson for 2004's Date School, and once again played Adam Sandler's sugar sweet girlfriend in director Peter Segal's romantic comedy Fifty-First Dates.

2005 brought yet another openly fluffy romantic comedy with Fever Pitch, in which she played the straight-girl against Red Sox super-fan Jimmy Fallon, but she soon changed gears, signing on to appear in Lucky You, a gambling drama by Curtis Hanson, director of L.A. Confidential and In Her Shoes. ~ Rebecca Flint Marx, All Movie Guide