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Then and Now: A Look Back at the ’90s Most Iconic Actresses

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Aug 26, 2024 / 6366 Views

Evan Walker

Many shining stars in Hollywood have dimmed with time, but true icons will never die. Here are some of the most iconic actresses of the ’90s, who carved out a place for themselves back then, and where they are now.

As it stands in 2024, cinematic and television productions can boast of undeniable polish, featuring incredible visual effects, cinematography, and thought-provoking plotlines, all brought to life by the stellar performances of Hollywood’s finest stars. Yet, for all the upward trajectory of modern television, certain cinematic productions of years long past have remained popular amongst audiences today.

Most notably, some iconic tv shows and movies of the ’90s have propelled their cast to global fame. Today, these screen actors remain imprinted upon our minds, their impact cemented within the halls of fame of pop culture. Whether by wielding their exceptional acting abilities to great success or by becoming icons through fashion and otherwise, these ’90s actresses have come a long way since then, and now remain enshrined among the greats.

Shannen Doherty: The actress who Charmed her way into our hearts

On July 13 2024, actress Shannen Doherty, known for her roles in top ’90s shows Charmed and Beverly Hills 90210 passed away after a long and arduous fight with cancer. Doherty’s original diagnosis in 2015 was that of breast cancer that had spread to one lymph node. Armed with courage and conviction, Doherty determined that she would fight her cancer diagnosis head on, undergoing treatment and a single mastectomy.

The actress proved successful in her first tussle against the disease, later going into remission in 2017. However, Doherty’s hard-won victory was bitterly cut short as the cancer returned as stage 4 in 2019, having metastasised to her bones and brain. By 2020, it was public knowledge that her cancer was terminal, with Doherty later sharing that she would need cancer treatment for the rest of her life. Over the next few years, the actress underwent chemotherapy and radiation, and in 2023, went through brain surgery to remove a tumour — which she named Bob, a move that reflected her cleverness, sharp wit, and acerbic brand of humour.

90s actresses then and now — Actress Shannen Doherty passed away on July 13 2024 from breast cancer. (Image: Shannen Doherty/Instagram)

Despite earning a reputation for being ‘difficult’ and ‘diva-like’ on-set, Doherty’s delivery and portrayals quickly endeared her to viewers of her shows. Perhaps most notable of these roles is that of Prue Halliwell in beloved ’90s cult classic Charmed, a family fantasy drama that follows the lives of the Halliwell sisters who discover that they are powerful witches endowed with magic.

Doherty’s portrayal of Prue was widely praised among fans and critics; leaning into themes of female empowerment, the actress gave a nuanced performance that married the complexities of family life and sisterhood with the burden of being the eldest child.

While the Halliwell sisters shared an incredible bond on screen, the same harmony did not extend offscreen. Rumours began to emerge that trouble was brewing between Doherty and her on-screen sister, former child star Alyssa Milano. When the dust had settled, Prue was dead, and Doherty had been fired — reportedly for being difficult to work with.

Holly Marie Combs pays tribute to Shannen Doherty:

“My better half of 31 years. There is a hollow in my chest and I can’t seem to catch my breath. A part of me is missing even though I know exactly what you would say to me right now. I know exactly what you would tell me to do… pic.twitter.com/VDj0g1tKnG
— Film Updates (@FilmUpdates) July 15, 2024

In the years since and leading up to her tragic end, Doherty had spoken up about her tussles in television. Not one to discount her own contributions to her reputation, the actress took a thoughtful approach in addressing her past. Speaking to Parade in 2010, she said, “I have a rep. Did I earn it? Yeah, I did. But, after a while, you sort of try to shed that rep because you’re kind of a different person.”

It’s easy to draw comparisons between the media’s treatment of Doherty, and its treatment of Britney Spears, Lindsay Lohan, and Katherine Heigl. Without making excuses for questionable behaviour, recent realisations have allowed us all to see a clear distinction between genuine malice and differing opinions and personalities. And in the high-stakes battleground that is Hollywood, one wrong move could mean the difference between being booked for a role and being cast out on exaggerated claims.

Prior to her death, Doherty also addressed her public fallout with Milano on her podcast, Let’s Be Clear with Shannen Doherty. In a riveting episode with explosive revelations, Doherty sat down with her on-screen sister, close friend and co-star Holly Marie Combs for candid conversations on their Charmed days.

The duo, who had been friends before they were cast for the series, remained in touch after Doherty’s departure from the show. Their decades-long friendship perfectly grounded their conversation, providing a glimpse into the drama as it had played out in the past. Speaking on the turbulence they had experienced on set with Milano, Combs shared, “There were no angels, there were no demons. We all had bad days, we all had good days. We all could have behaved better at certain points but there was a lack of awareness of a bigger broader picture.”

With the shifting of modern perspectives, society and the media have reframed Doherty’s reputation. And while it has been a long time coming, it bears noting that the actress, who has arguably left an indelible mark on the turbulent landscape of Hollywood, will be remembered as she truly was: A courageous woman, a fighter, an incredible actress, and someone who never afraid to speak her truth.

Iconic ’90s actresses, how they were back then, and where they are now

Lindsay Lohan

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No list of the most iconic 90s (and noughties) actresses is complete without mention of Lindsay Lohan, whose performance in The Parent Trap (1998) firmly cemented her place among the greatest child stars of our time. Over the years, the actress has lent her talent to shows such as Get A Clue (2002), Freaky Friday (2003), Mean Girls (2004), Georgia Rule (2007), and Just My Luck (2006), with guest and cameo roles in popular TV shows like 2 Broke Girls, That ‘70s Show, Ugly Betty, and even Glee. In her heyday, Lohan also dabbled in music, with two studio albums and six singles to her name.

However, Lohan’s path to success has been paved with controversy and calamity. Between 2007 and 2015, the starlet fell prey to vices including drugs and alcohol, and was saddled with problems such as overspending and near-bankruptcy.

Considering the circumstances, it is understandable that the actress’ finances has suffered due to her many predicaments. However, while her net worth as of 2024 sits at a modest USD 2 million — a far cry from full recovery — Lohan herself has made great strides towards her comeback and the rejuvenation of her career. Having signed a three-movie deal with Netflix, the first two of which are Falling For Christmas (2022) and Irish Wish (2024), Lohan’s sterling recovery is proof positive that comebacks are always in the cards for those who work hard. She’s also currently filming Freaky Friday 2, which will release in 2025 and sees original cast members Jamie Lee Curtis and Chad Michael Murray reprising their roles alongside Lohan.

The Colemans are back and coming to theaters in 2025! The sequel to Freaky Friday is now in production! pic.twitter.com/0PfBycJRzi
— Walt Disney Studios (@DisneyStudios) June 24, 2024

Jennifer Aniston

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From 1994 to 2004, one could not claim to be a fan of the comedy genre without knowing of Friends — and by extension, of Jennifer Aniston. Known by her fans for her impeccable comedic timing and exquisite fashion sense both on-and-off-screen, Aniston’s career is marked by incredible highs, both in television and on the silver screen. Besides her career-making role as Rachel Green in Friends, Aniston’s best works also include performances in Marley & Me (2008), He’s Just Not That Into You (2009), Horrible Bosses (2011), We’re The Millers (2013), and Netflix’s comedy whodunnit Murder Mystery (2019).

Today, Aniston’s net worth stands at a tidy USD 320 million, reflecting her popularity and success as an actress. Her most recent works include the critically acclaimed comedy drama The Morning Show, of which season 4 is currently in production.

Lori Loughlin

Lori Loughlin may have gained fame and fortune as Aunt Becky in Full House (1988 – 1995), but it wasn’t until her involvement in a North American college admissions bribery Scandal that she really gained infamy and public scrutiny. The Scandal, which hit a fever pitch in 2019, also cast the shadow of Scandal over Felicity Huffman (of Desperate Housewives fame) along with dozens of other parents, who were found to have paid up to USD 6 million to secure their children spots at elite universities.

At the heart of the Scandal was ringleader Rick Singer, who received payments from high-profile parents to fabricate applications for prospective students. Along with her husband Mossimo Giannulli, Loughlin was found guilty of paying USD 500,000 to secure her daughters Isabella and Olivia spots at the University of Southern California. They were later charged with conspiracy to commit money laundering and conspiracy to commit federal programs bribery. Upon pleading guilty, Loughlin was sentenced to two months in prison, and received a USD 150,000 fine and 100 hours of community service; Giannuli was sentenced to five months in prison and received a USD 250,000 fine plus 250 hours of community service.

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Since her release from prison, Loughlin has appeared in several movies including Fall Into Winter (2023) and When Hope Calls (2023). She had previously appeared in Netflix’s reboot of Full House, Fuller House (2016 – 2018), 90210 (2008 – 2012), Summerland (2004 – 2005), and When Calls The Heart (2014 – 2019). As of 2024, she has a net worth of USD 80 million.

Sarah Michelle Gellar

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One of the most iconic actresses of the 90s, Sarah Michelle Gellar gained popularity playing leading roles in the most popular shows of then among other stars who are still popular now. While she has largely stayed out of the limelight since her heyday, Gellar’s impressive resume is led by her role as Buffy in ’90s cult favourite Buffy The Vampire Slayer (1997 – 2003).

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Hailed the veritable ‘scream queen’ of the 90s, Gellar’s roles often marry strength, sensitivity, and snark in the horror genre — beyond Buffy, she has also appeared in I Know What You Did Last Summer (1997), Scream 2 (1997), Cruel Intentions (1999), Scooby-Doo (2002), The Grudge (2004), The Return (2005), The Grudge 2 (2006), and Possession (2009) among others. Her work in the industry has garnered her an impressive net worth of USD 30 million as of 2024; most recently, she appeared in Do Revenge (2022) alongside Sophie Turner, Camila Mendes, and Maya Hawke, and starred in TV series Wolf Pack (2023).

Reese Witherspoon

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While Reese Witherspoon may be best known for her role as the inimitable Elle Woods in Legally Blonde (2001), she first found success starring alongside Ryan Philippe and Sarah Michelle Gellar in Cruel Intentions (1999). Her prominence in the cult-classic movie then propelled her to international fame, with a string of highly rated projects following including Sweet Home Alabama (2002), The Importance of Being Earnest (2002), Vanity Fair (2004), Just Like Heaven (2005), and Water For Elephants (2011). In this time, Witherspoon also appeared in a guest role in Friends, where she portrayed Rachel’s younger sister.

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While Witherspoon herself has admitted to spending a few years between 2007 and 2012 ‘floundering, career-wise’, she soon regained her footing by founding production house Pacific Standards (Now a part of her media company Hello Sunshine). As an aspiring producer, Witherspoon’s goal was to put forth projects with strong female leads, which she felt Hollywood lacked. She went on to produce Gone Girl (2014), and later produced and starred in Wild (2014), marking her definitive and triumphant return to the forefront of Hollywood. Today, Witherspoon boasts a net worth of USD 400 million, with some of her most recent projects including The Morning Show alongside Jennifer Aniston, as well as Sing (2016), Sing 2 (2021), Big Little Lies (2017 – 2019), and Netflix romantic comedy Your Place Or Mine (2023).

Kate Winslet

Fewer actresses can claim to have impacted Hollywood in the ’90s the way Kate Winslet has, with enthralling performances in book-to-movie adaptations including Sense and Sensibility (1995) and Hamlet (1996). However, it wasn’t until her breakthrough role as Rose Dewitt Bukater in James Cameron’s Titanic (1997) alongside Leonardo DiCaprio that she truly rose to prominence. Despite Titanic’s remarkable success, the actress was determined to follow the beat of her own drum, turning down offers to star in Shakespeare in Love (1998) and Anna and the King (1999). Instead, Winslet focused her attentions upon Hideous Kinky (1998), a semi-autobiographical book-to-film adaptation that tells the tale of a single mother from England seeking a new life in 1970s Morocco.

Further taking the beaten path, Winslet then starred alongside Joaquin Phoenix in Quills (2000); she then worked on Iris (2001), The Life of David Gale (2003), Eternal Sunshine of the Spotless Mind (2004), Finding Neverland (2004), Little Children (2006), The Holiday (2006), and The Reader (2008), among others. That same year, she reunited with Leonardo DiCaprio for Revolutionary Road, and in 2014, reunited with Alan Rickman for A Little Chaos.

Within Winslet’s inspired portfolio of roles, one thing remains clear: She has no desire to be typecast, with stellar performances across multiple genres that are proof positive of her success in this regard. Her most recent projects reflect her continued dedication to her craft, and include Mare Of Easttown (2021), Avatar: The Way of Water (2022), and The Regime (2024). As of 2024, she has a net worth of USD 65 million.

Winona Ryder

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Winona Ryder first rose to prominence in 1988, when she was cast by director Tim Burton to play goth teenager Lydia in what would be her breakout movie, Beetlejuice. The movie was largely successful, becoming a cult classic that has endured to this day, propelling Ryder into international superstardom at the ripe old age of 17. Ryder then dove headfirst into acting, securing top roles in film that made her one of the most iconic actresses of the 90s, ensuring her longevity in the industry even now.

Key among her notable movies is Edward Scissorhands (1990), in which she starred alongside Johnny Depp, to whom she became engaged in 1990 when she was about 19 years old. While the two did not end up tying the knot, their eight-year age gap raised eyebrows at the time, cementing Ryder’s image in the public eye as a ‘wild child’.

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Between 1990 and 2000, Ryder appeared in several well-received films, including Bram Stoker’s Dracula (1992), The Age of Innocence (1993), Little Women (1994), Alien: Resurrection (1997), and Girl, Interrupted (1999). By then a household name, Ryder too fell prey to the pitfalls of Celebrity, with wrongfully prescribed drug use impairing her judgment and leading to her arrest on shoplifting charges in late 2001. In December 2002, she was convicted of grand theft and shoplifting and received three years of probation, 480 hours of community service, USD 3,700 in fines and USD 6,355 in compensation to the Saks Fifth Avenue store she had shoplifted from. Additionally, Ryder was ordered to undergo psychological and drug counselling.

By all accounts, Ryder’s career appears to have recovered. As of 2024, she has appeared in numerous critically acclaimed movies, including Star Trek (2009) and Black Swan (2010). Most recently, she has also appeared in Netflix’s horror drama series Stranger Things. As of 2024, her net worth stands at a tidy USD 18 million.

Natalie Portman

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Actress Natalie Portman first gained popularity in 1994, when she portrayed the character of Mathilda, protégée to a hitman, in Léon: The Professional. Given the subject matter, which included violent and sexual themes, Portman’s mother was initially hesitant about letting Portman, who was merely 13 at the time, take the role. Director Luc Besson eventually agreed to amend the script to exclude themes of nudity and murder for the character, which ultimately led to Portman’s film debut as part of the cast. By 1999, Portman had been cast in Star Wars: Episode 1 – The Phantom Menace, in which she appeared as Queen Padme Amidala, a role that cemented her face amongst Hollywood’s most popular stars at the time.

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Over the years, Portman has carved out a niche for herself, her incredible performances earning Academy and Golden Globe award nominations. For her stunning performance in Black Swan (2010), Portman took home the Academy Award win for Best Actress, winning critical acclaim with her nuanced performance blending obsession and perfectionism.

Other notable movies within her impressive portfolio include Star Wars: Episode II – Attack of the Clones (2002), Cold Mountain (2003), Garden State (2004), Star Wars: Episode III – Revenge of the Sith (2005), V for Vendetta (2005), The Other Boleyn Girl (2008), and No Strings Attached (2011).

Interestingly, Portman has also appeared in several music videos for Sir Paul McCartney, including Dance Tonight and My Valentine. She later joined the Marvel Cinematic Universe in 2011 when she was cast as Jane Foster for Thor; she later reprised her role alongside Chris Hemsworth for Thor: The Dark World (2013), Avengers: EndGame (2019), and Thor: Love and Thunder (2022). As of 2024, she boasts a net worth of USD 90 million, courtesy of her acting projects as well as her various endorsement deals — most notably as the face of Miss Dior.

Julia Stiles

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Born and raised in New York City, actress Julia Stiles first rose to prominence for her role in 10 Things I Hate About You (1999), in which she portrayed acerbic teenager Kat Stratford opposite the free-spirited Patrick Verona of the late Heath Ledger. The romantic comedy, which has now become a cult favourite was an instant hit, earning Stiles a place among the most iconic 90s actresses, and then some more.

Stiles went on to star in The Bourne Identity (2002), Mona Lisa Smile (2003), The Prince and Me (2004), and The Bourne Ultimatum (2007) among others. In 2010, she earned a guest role in crime drama series Dexter, and later returned to the silver screen in Silver Linings Playbook (2012). Other notable projects include Hustlers (2019), Riviera (2017 – 2020), The Lake (2022 – 2023), and Dragons: The Nine Realms. As of 2024, her net worth is an estimated USD 12 million.

Alicia Silverstone

Iconic 90s actress Alicia Silverstone first rose to prominence in 1992, when she was cast in erotic thriller The Crush. To meet the gruelling demands of Hollywood, Silverstone became legally emancipated aged 15, allowing her to spend her time on set as needed — her decision paid dividends, as she later won the awards for Best Breakthrough Performance and Best Villain at the 1994 MTV Movie Awards. Silverstone’s work on The Crush also paved the way for her next projects: A trio a music videos for Aerosmith including those for Cryin’, Amazing, and Crazy.

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Following the widespread success of the music videos, Silverstone was cast as Cher Horowitz in Clueless (1995), in what would become the most important role of her career. Clueless became an instant cult hit, propelling both Silverstone as well as her co-star Paul Rudd to greater heights. Silverstone subsequently signed a deal with Columbia-TriStar for between USD 8 – 10 million and also took home the awards for Best Female Performance and Most Desirable Female at the 1996 MTV Movie Awards.

Beyond acting, Silverstone has also published two cooKBOoks, The Kind Diet (2009) and The Kind Mama (2014); as of 2024, she has a net worth of about USD 20 million.

Drew Barrymore

A former child star, Drew Barrymore’s very first credit for television was as Bobbi Graham in Suddenly, Love (1978), when she was just three years old. She later gained prominence by appearing as Gertie in E.T. the Extra-Terrestrial (1982). Following her success as a child star, Barrymore became a Hollywood mainstay with a cult following, appearing in a series of popular movies including the Charlie’s Angels series, Donnie Darko (2001), Never Been Kissed (1999), 50 First Dates (2004), and He’s Just Not That Into You (2009) among others. However, one of Barrymore’s most iconic roles came in 1998, when she played Danielle in the Cinderella-inspired romantic drama Ever After.

Like many child stars, Barrymore fell prey to the pitfalls of Hollywood, developing addictions and undergoing rehab all by the ripe old age of 15. However, she made an outstanding recovery, and is widely known to be one of Hollywood’s greatest successes with a net worth of USD 85 million as of 2024. Today, she boasts credits as an author, actress, and producer, and currently hosts her own talk show, The Drew Barrymore Show. Her most recent projects include a guest role in Family Guy and a lead role in Netflix’s highly rated comedy series Santa Clarita Diet.

Christina Ricci

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An icon with an unforgettable face, actress Christina Ricci first shot to fame as Wednesday in The Addams Family (1991), charming the world with her inimitable deadpan expressions. Further banking on her typically ‘goth’ appearance, she reprised the role of Wednesday in Addams Family Values (1993), and later appeared as Kat in Casper (1995). By 1999, Ricci had fully transitioned into ‘adult’ roles, appearing as the lead female character in Tim Burton’s Sleepy Hollow alongside Johnny Depp. For her performance as Katrina Van Tassel in the film, Ricci received the Saturn Award for Best Actress, cementing her place as one of the most iconic 90s actresses that continue to be relevant today.

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Ricci later appeared in 200 Cigarettes (1999), Bless the Child (2000), The Man Who Cried (2000), and Prozac Nation (2001) among other films. Additionally, the actress has also found success on television, landing guest roles in top TV dramas like Grey’s Anatomy, Malcolm in the Middle, Ally McBeal, and The Good Wife. She has also appeared as the titular character of TV crime drama miniseries The Lizzie Borden Chronicles (2015) and Z: The Beginning of Everything (2015 – 2017).

More recently, Ricci has graced our screens in The Matrix Resurrections (2021), Yellowjackets (2021 – 2023), and even showed her support for Netflix’s Wednesday (2022) by appearing as series antagonist Marilyn Thornhill. As of 2024, Ricci has a net worth of about USD 8 million.