The '90s It Girls You Wanted (and Still Kind of Want) to Be

Drew may have had a lot of ups and downs during her career, but the '90s was when she really hit her stride. She was dating hot guys; she was wearing flowers in her hair; she was posing for Playboy; and she was flashing her boobs to David Letterman. She palled around with Liv Tyler and Courtney Love and was rumored to have had a fling with Sassy and Jane founder Jane Pratt. She was a real badass — and even though she's a little more settled down these days, we just know Drew still has that rebellious streak.

Winona took the '90s by storm with leading roles in Edward Scissorhands, Girl, Interrupted, and Reality Bites. She dated Johnny Depp and Matt Damon and rose to icon status thanks to her unique, dark performances and enviable pixie cut. Winona forever.

Halle Berry was the go-to girl for '90s movies with primarily black casts — she starred in Boomerang, Jungle Fever, and Strictly Business, and it wasn't long before mainstream Hollywood took note of her talent, beauty, and charisma on and off screen. Oh, and she still happens to be aging backwards.

Back in the '90s, Kate Moss was drinking, smoking, and gracing the pages of Vogue. You know what Kate Moss is doing today? Drinking, smoking, and gracing the pages of Vogue.

Naomi Campbell was walking runways left and right in the '90s (usually alongside her BFF Kate Moss) and giving black girls everywhere hope that they too could become world-famous supermodels. Icon!

Alicia Silverstone became a star thanks to her performance as self-obsessed Beverly Hills princess Cher Horowitz in a little 1995 cinematic masterpiece called Clueless. Not only are women still quoting the film and dressing up as her character for Halloween every year, but Alicia also gave us die-hard fans a subtle nod to her alter ego when she wore a custom-made ruby-red Christian Siriano gown at the 2016 CFDA Awards.

The truth is, Liv Tyler was going to be cool no matter what she did. The daughter of model Bebe Buell and Aerosmith frontman Steven Tyler was not only '90s rock 'n' roll royalty, but her roles in movies like Empire Records, Stealing Beauty, and Armageddon throughout the decade launched her into an entirely new stratosphere in Hollywood. Also, let's not forget her epic, controversial appearance in Aerosmith's "Crazy" video alongside fellow '90s darling Alicia Silverstone.

Don't act like you didn't chop off all your white tank tops and jump around your bedroom while screaming along to "Just a Girl." The best part is: Gwen Stefani is still just as cool, stylish, and ripped as she was back in the day.

Before she taught us about macrobiotic eating, vagina steaming, and conscious uncoupling, Gwyneth was a '90s movie darling, starring in films like Seven, Great Expectations, The Talented Mr. Ripley, and Shakespeare in Love, for which she won an Oscar in 1999. These days, she's a lifestyle guru, mom of two cute kids, and BFF of Beyoncé. Not a bad evolution.

By the '90s, Janet had fully stepped out of the shadow of her famous brothers and made a name for herself with hits like "Runaway," "That's the Way Love Goes," and "Got Til' It's Gone" and a starring role opposite Tupac Shakur in Poetic Justice. In one of her most daring moves, Janet covered the Sept. 16, 1993, issue of Rolling Stone topless, with a man holding her breasts from behind.

Is Courtney perfect? No. Is she a total badass? Absolutely. Nobody did babydoll dresses and smeared red lipstick like Courtney Love — and to this day, nobody looks as cool shredding their guitar with their foot up on the amp.

Lisa Bonet went from The Cosby Show and A Different World to marrying Lenny Kravitz and giving birth to their daughter, actress Zoë Kravitz. To this day, she's still one of the poster children for the bohemian black girl, and Zoë is totally following in her badass footsteps.

We didn't know whether to love or hate Claire Danes back in the '90s: after all, this is the girl who got to romance both Jared Leto and Leonardo DiCaprio on screen, but she also just seemed like she'd be a really great BFF.

Natalie Portman made her film debut in 1994's Léon: The Professional, and nabbed a major role (and tons of critical acclaim) in Beautiful Girls two years later. Before she won our hearts in Closer, Garden State, and Black Swan in the 2000s, though, Natalie gave us literal goals when she took time off from acting to casually study psychology at Harvard University in 1999.

Fiona Apple was only 18 when she dropped her debut single "Criminal" in 1996 (full disclosure: Tidal was the first album this POPSUGAR editor ever bought). The song's video grabbed headlines for its sexual undertones — which were then considered really controversial but now seem ridiculously tame — and the following year, Fiona nabbed a Grammy and gave a scathing acceptance speech when she won an MTV VMA, telling the crowd, "This world is bullsh*t." When will your fave?

Before she was "holding two photos" in her hand and picking the next America's Next Top Model, Tyra Banks was stomping the runways for Chanel and Christian Dior and starring in Michael Jackson's "Black or White" video, as well as one of Will Smith's many love interests on The Fresh Prince of Bel-Air. She was also the first black model to cover GQ, the Sports Illustrated Swimsuit Issue, and a Victoria's Secret catalog. NBD.

Chloë Sevigny started out as a Sassy model and intern thanks to her eclectic style and made waves with her controversial, meaty roles in Kids, Gummo, and Boys Don't Cry — the films made her an indie movie darling and a '90s fashion favorite. Her influence still runs deep: in 2015, Chloë released her own book, a memoir with personal photos and memorabilia detailing her unique Hollywood evolution.

Brandy had us singing along to her hits "I Wanna Be Down" and "Sittin' Up in My Room" while also watching her on TV — her Moesha character, Moesha Mitchell, was everything we wanted to be: smart, quick-witted, and headstrong. Brandy inspired little girls even more in 1997 when she became the first-ever black actress to portray Cinderella in a two-hour TV special with her mentor, Whitney Houston. Oh, and "The Boy Is Mine" with Monica? Classic middle school dance jam.

Christina Ricci's breakthrough role as Wednesday Addams in The Addams Family films helped catapult her into teen icon status — how much did you love her as Roberta in Now & Then and Kat in Casper? Were she and Devon Sawa not some sort of '90s movie power couple?

Nia Long starred on the big screen in classics like Boyz in the Hood, Friday, Made in America, and Soul Food, and also won our hearts as Will Smith's girlfriend Lisa on The Fresh Prince of Bel-Air. She's still an all-around beauty, and much like Halle Berry, is the definition of the old adage "black don't crack."

Hello? "The Rachel?" Jennifer Aniston had everyone running to their hairstylists to get the shaggy layered cut that she wore on Friends, and even though she's since admitted that she found the style "cringe-y," it still belongs in a beauty museum somewhere. While she was portraying Rachel Green on the hit NBC sitcom, Jen was also starring in movies like She's the One, Picture Perfect, The Object of My Affection, and Office Space.

As one of the founding members of Sonic Youth, Kim Gordon was a force to be reckoned with; she was a guitarist, songwriter, visual artist, and feminist badass. She and then-husband Thurston Moore inspired legions of fans with the band's "no-wave" music, and Kim's messy blonde hair, dark eyeliner, and rebellious sense of style became a '90s-girl aesthetic.

Tatyana Ali became a household name thanks to her role as Will Smith's young cousin Ashley Banks on The Fresh Prince of Bel-Air. She was sweet, talented, and got to hang out with Will Smith all day. Remember her 1998 song "Daydreamin'"?

Sofia Coppola starred in a few music videos by '90s bands like The Black Crowes, Sonic Youth, and The Chemical Brothers and was featured as a model in teen magazines like Seventeen and YM. She cofounded the fashion brand Milk Fed in Japan, and was dating director Spike Jonze, whom she'd go on to marry in 1999. That same year, she made her feature film directing debut with The Virgin Suicides. By that time, the daughter of legendary director Francis Ford Coppola had become synonymous with some of the arbiters of '90s cool: Karl Lagerfeld, Juergen Teller, and Marc Jacobs.

Liz Phair's 1993 album Exile in Guyville has been called "the most glorious, girly 'f*ck you' ever," and even that seems like an understatement. It was a true feminist proclamation and one that couldn't have come sooner, because we wanted to be as brazen, candid, and confidently flawed as Liz was. Would there have been an Alanis Morissette without Liz Phair? Maybe not.

Bonus: Exile is still completely relevant today, especially "Divorce Song" and "F*ck and Run."

Rosario Dawson's big screen debut was in the controversial (and disturbing) 1995 movie Kids along with fellow It girl Chloë Sevigny. She was the quintessential New York City kid; a street-smart, fast-talking fighter. These days, she's still using her wisdom and outspokenness to champion causes close to her heart, like the Lower East Side Girls Club, Voto Latino, and Amnesty International.