Iconic leading ladies of the '90s - How they've changed | Gallery

By Gena Oppenheim 8:08am PDT, Mar 19, 2020

There's no sure-fire formula for making a hit movie — especially one as timeless as 1990's "Pretty Woman" — but all bets are off when there's a talented female lead like Julia Roberts in the equation. It'll be 30 years since the rom-com was released on March 23, so Wonderwall.com is taking a closer look at iconic leading ladies of the '90s and where they are now, starting with Julia. Her million-dollar smile dominated the box office in a number of other smash hits that decade: "Sleeping with the Enemy," "I Love Trouble," "My Best Friend's Wedding," "Notting Hill" and "Runaway Bride." But the Oscar winner's come quite a long way since then. Keep reading to uncover how Julia and more '90s icons have changed!

Julia Roberts has steadily maintained her leading-lady status over the last three decades — a tough thing to do as a woman in Hollywood. She won her first Oscar (and third Golden Globe) for her stellar performance in the 2000 biographical legal drama "Erin Brockovich." The kicker? She also set a record, becoming the highest paid actress at the time thanks to her $20 million paycheck. The same year, she met her second (and current) husband, cameraman-turned-cinematographer Daniel Moder, while filming "The Mexican" with Brad Pitt. Julia kept making great films that decade — "Ocean's Eleven," "Charlie Wilson's War," "Duplicity" — all while balancing her then-new role as a mom to twins Hazel and Phinnaeus and son Henry. Over the last decade, she's been focused on more serious roles, starring in 2010's soul-searching biopic "Eat Pray Love," 2013's family drama "August Osage County" and 2018's addiction tearjerker "Ben is Back." Yet another reason Julia's still on top: She keeps on changing with the times and in 2018 headlined the thrilling Amazon Prime web series "Homecoming."

Alicia Silverstone's role as spoiled teen Cher Horowitz in 1995's "Clueless" put the then-budding young actress on the map and turned the coming-of-age flick into a cult classic. Her star power kept rising throughout the '90s with other leading roles in "Batman & Robin" (she played Batgirl) and the retro rom-com "Blast from the Past."

Alicia Silverstone will forever be a '90s teen idol, but she's changed a lot since her as-if days! She now splits her time between acting, activism and parenting Bear, her son with rocker ex-husband Christopher Jarecki (they ended their 13-year marriage in 2018). The working mom has kept up with her career in a handful of supporting roles including her most recent as a marriage counselor in the upcoming comedy "Bad Therapy." She also nabbed TV gigs in projects like the 2003 NBC sitcom "Miss Match" (for which she scored a Golden Globe nom) and Paramount's 2018 drama "American Woman." But since becoming a vegan two decades ago, much of Alicia's focus has been on advocating for her cruelty-free lifestyle — she even posed nude for PETA's "I'd Rather Go Naked" anti-fur campaign! She also branched out into publishing and penned a vegan cookbook called "The Kind Diet" in 2009, which she followed with the launch of her Kind Life blog. She caught some initial flack over the site after sharing a video of herself feeding her then-baby chewed food from her mouth, but the dust settled and she's still delivering health-conscious content to this day.

Kate Winslet was the ultimate queen of period pieces (and the world) in the '90s as she starred in the big-screen adaptations of Jane Austen's novel "Sense and Sensibility" and Shakespeare's play "Hamlet." But her most stand-out role of the decade was as Rose in 1997's "Titanic" alongside Leonardo DiCaprio.

Kate Winslet scored Oscar noms for "Sense and Sensibility" and "Titanic" in the '90s but didn't actually win a best actress Academy Award until 2009, for her work in "The Reader." Accolades aside, she's generated a steady flow of box office hits over the last 20 years: "The Holiday" with rom-com icon Cameron Diaz, "Revolutionary Road" with repeat co-star Leonardo DiCaprio, the tech biopic "Steve Jobs" and the survival saga "The Mountain Between Us." Kate also tried her hand at TV with HBO's 2011 miniseries "Mildred Pierce" and came out an instant Emmy winner! She upped the ante when she signed on to executive producer and star in her second project with HBO, the upcoming 2020 small-town detective series "Mare of Easttown." But some of Kate's biggest life changes revolve around her unconventional personal life as the mom of three kiddos with three different dads. She shares daughter Mia with her first ex-husband, director Jim Threapleton, son Joe with her second ex, director Sam Mendes, and youngest son Bear with her current hubby, Ned Rocknroll (don't worry, he took his mom's last name).

Gwyneth Paltrow only started making feature films in the early '90s, but her career took off fast! By the end of the decade, she'd become one of Hollywood's finest leading ladies with credits in blockbusters like "Hook," "Seven" and "The Talented Mr. Ripley." She also starred in a slew of period pieces: "Emma" (pictured), "Great Expectations" and "Shakespeare in Love."

Gwyneth Paltrow rounded out her first decade in Hollywood with an Oscar and a Golden Globe for her work in 1998's "Shakespeare in Love" as well as two failed high-profile romances with Brad Pitt and Ben Affleck. By 2003, she was married to Coldplay rocker Chris Martin and pregnant with daughter Apple. She gave birth to her second child, son Moses, in 2006, but kept making blockbusters! Gwyneth branched out genre-wise, tackling comedy in the early 2000s with "The Royal Tenenbaums" and "Shallow Hal." Then she tried some sci-fi and action within the Marvel Cinematic Universe with "Iron Man," "Avengers" and "Spider-Man" movies. She even put her (surprise!) singing talents on display in movies like "Duets" and "Country Strong" before moving to TV with an Emmy-winning guest role on FOX's musical hit "Glee." Gwyneth's career path changed drastically in 2008 with the launch of her high-end lifestyle newsletter, Goop, which quickly expanded into a huge online entity and now boasts its own wellness summit, print magazine, podcast and Netflix docuseries. The actress-turned-blogger (and four-time cookbook author) used the site as a positive platform to discuss relationships when she and Chris amicably split in 2014, coining a new term for an amicable divorce: "conscious uncoupling." She moved on with writer-producer Brad Falchuk and remarried in 2018, though she and Chris remain co-parenting pals.

Sandra Bullock became a bona fide leading lady after nailing a modern damsel-in-distress role as a woman forced to frantically drive a city bus rigged to detonate in 1994's "Speed," which co-starred Keanu Reeves. For the remainder of the decade, she dominated the box office in both thrillers and rom-coms like "While You Were Sleeping," "The Net," "Hope Floats" and "Practical Magic."

There's so much more to Sandra Bullock than just being a leading lady. Nowadays, she balances her role as a working mom of two with a non-stop acting career and her own production company, Fortis Films. She adopted her first little one, son Louis, in the midst of a devastating divorce from vehicle customizer Jesse James — multiple women came forward outing his infidelity — in 2010. Sandra left Jesse in the dust and moved on with her life, adopting a second child on her own, daughter Laila, in 2015. The same year, the fierce mama also found love again with her current flame, photographer Bryan Randall (they may even be secretly married). And her career never faltered through it all! Sandra really upped her game in the early 2000s — she executive produced a sitcom for ABC, "George Lopez," and starred in a slew of rom-com hits like "Miss Congeniality," "The Lake House" (alongside repeat co-star Keanu Reeves) and "The Proposal." To round out the decade, she took home an Oscar and a Golden Globe for her portrayal of football mom Leigh Anne Tuohy in 2009's sports biopic "The Blind Side." More recently, she lent her voice to the animated flick "Minions" and headlined the heist spinoff "Ocean's 8." But Sandra's transition to Netflix in 2018's "Bird Box" was most notable — the post- apocalyptic thriller broke their debut-week record with over 45 million views. She's already working on another series, "Unforgiven," for the streaming platform.

Demi Moore was a newcomer to Hollywood in the '80s but hit her stride with at least one major blockbuster every year of the '90s. To name a few: "Ghost," "A Few Good Men," "Indecent Proposal," "Now and Then," "Striptease," "If These Walls Could Talk" and the military drama "G.I. Jane" (pictured here, with a fully shaved head!).

Demi Moore solidified her place as a true '90s icon when she scored a Golden Globe nod for her steamy performance alongside Patrick Swayze in "Ghost" and an Emmy nom for her work in the TV movie "If These Walls Could Talk." But her big-screen career slowed down majorly in the decades to follow with a few supporting roles in films like the "Austin Powers" franchise, the biopic "Bobby," the Wall Street drama "Margin Call" and, more recently, "Corporate Animals." She also had a guest role on the FOX series "Empire" and is slated to appear on the upcoming show "Brave New World" on the Peacock streaming service. Demi's personal life, however, has been much more eventful thanks to two high-profile marriages (and divorces) in the last two decades. She split from husband Bruce Willis — with whom she shares daughters Rumer, Scout and Tallulah — in 2000 and married Ashton Kutcher, who's 16 years her junior, in 2005. In 2019, she released the tell-all memoir "Inside Out," which details the demise of their relationship. She revealed that she faced addiction issues during and after their union and ended up in rehab for an eating disorder after they separated in 2011 as well as how she and the actor had intimate encounters with other women before he starting cheating on her altogether, she claimed. The juicy memoir landed her on The New York Times bestseller list!

Drew Barrymore was only 7 when she appeared in her breakout role in 1982's "E.T. the Extra-Terrestrial." She basically grew up on the big screen throughout the '90s, going from adolescence in "Poison Ivy" and "Batman Forever" to young adulthood in rom-com classics like "The Wedding Singer," "Ever After" and "Never Been Kissed" (pictured).

Drew Barrymore grew up in the limelight so it's no surprise she's been able to maintain and build on her child-star status (or that she's penned two juicy memoirs, "Little Girl Lost" and "Wildflower" about her unconventional childhood). She continues to act on both the big and small screens, run her own production company, Flower Films, branch out into cosmetics with a successful cruelty-free line, Flower Beauty, and develop both a clothing line and a wine label. She also has two young daughters, Frankie and Olive, with her third ex-husband, art consultant Will Kopelman (who's the son of a former Chanel CEO). Drew — who was briefly married to bar owner Jeremy Thomas and comedian Tom Green and dated Strokes drummer Fabrizio Moretti and actor Justin Long before settling down again — has been single since her divorce from Will in 2016. But the working mom has stayed busy in Hollywood over the years with tons of box office comedy hits: "Charlie's Angels," "50 First Dates," "He's Just Not That Into You" and "Blended" (with repeat co-star Adam Sandler). As for her TV work, she won a Golden Globe for her performance in 2009's HBO biopic "Grey Gardens" and made the shift to streaming with 2017's Netflix series "Santa Clarita Diet." Up next, she'll star in the comedy film "The Stand-In."

Meg Ryan's leading role in 1989's "When Harry Met Sally" catapulted her rom-com career well into the '90s. She not only headlined "Prelude to a Kiss," "French Kiss" and "City of Angels" but also teamed up with Tom Hanks twice that decade to create the classic love stories "Sleepless in Seattle" (pictured) and "You've Got Mail."

Cut to today and Meg Ryan is missing in action! In the tail end of the 2010s, she took a major step back from the limelight to focus on her personal life. She dated rocker John Mellencamp for two lengthy runs during the early and late 2010s but they called off their engagement in 2019. She has an adult son, Jack Quaid, from her marriage to Dennis Quaid (they divorced in 2000) and a daughter, Daisy, whom she adopted on her own in 2006. But even with the challenges of motherhood, Meg continued to act throughout the early aughts in movies like "Hanging Up," "Proof of Life," "Kate and Leopold" and "The Women." She went totally AWOL after making her directorial debut with the 2015 war drama "Ithaca," which is based on William Saroyan's 1943 novel "The Human Comedy." At least she got the chance to reunite with repeat co-star Tom Hanks — who had a supporting role in the film — and to work alongside her actor son Jack for the first time. If Meg's actually done with Hollywood, it's a good thing Jack's star is on the rise — he scored a leading role in Amazon Prime's new sci-fi series "The Boys."

Sharon Stone's performance as seductive serial killer Catherine Tramell in 1992's "Basic Instinct" turned her into a strong (and sexy) female icon. She was even able to hold her own in 1995's epic crime drama "Casino" alongside Hollywood powerhouses like Robert De Niro and Joe Pesci.

Sharon Stone's then-controversial interrogation scene in "Basic Instinct" — you know, the one where she keeps uncrossing her legs to distract detectives — remains an infamous moment in Hollywood history. But the erotic thriller's success and her Golden Globe win for her performance in "Casino" was only a jumping off point in her career. Sharon won an Emmy in 2004 for a guest spot on the ABC drama "The Practice" (after taking a short hiatus from acting due to a brain aneurysm) but finally jumped on the streaming bandwagon in 2019 with Netflix's hit series "The New Pope" and the satirical comedy "The Laundromat." She's also slated to appear in their upcoming series "Ratched" based on the novel "One Flew Over the Cuckoo's Nest." As for her personal life? Sharon's the proud mother to three adopted sons — Roan, Laird and Quinn — though she hasn't been as lucky in love thanks to two failed marriages to producer Michael Greenberg in the '80s and newspaper editor Phil Bronstein in the '90s. But she's all smiles now and was last linked to hunky real estate mogul Angelo Boffa, who's 19 years her junior. Before him, she dated model Martin Mica, who was 27 years her junior!

Jodie Foster — who's been acting since she was 4 years old — paved the way for strong female leads in the '90s when she starred as FBI agent Clarice Crawford in the 1991 psychological thriller "The Silence of The Lambs." Throughout the decade, she headlined a handful of other powerful films like "Nell," "Contact" and "Anna and the King."

Toward the end of the '90s, Jodie Foster already had two Oscar and Golden Globe wins under her belt for her work in "The Accused" and "Silence of the Lambs" along with her own production company, Egg Pictures (though it shut down in the early 2000s). She continued acting in big pictures like "Panic Room," "Inside Man" and "Hotel Artemis" but has focused more on directing in recent years, most notably with films like 2016's "Money Monster." Though Jodie likes to keep her personal life private, she publicly came out as a gay woman in an emotional speech at the 2013 Golden Globes, revealing the next year that she had secretly married photographer Alexandra Hedison. She also has two sons — Kit and Charles — from her past relationship with Cydney Bernard in the '90s.