By Megan Riedlinger
8:37am PST, Feb 28, 2024
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It's hard to believe, but pop culture icon Monica Lewinsky turned 50 on July 23, 2023. She celebrated her big day by taking to Instagram to share a video featuring several childhood photos of herself: "Happy 50th birthday to me! I can't believe this little one made it to the best past decade so far. So grateful for the love [and] encouragement I've received these last 10 years. Helluva ride so far!" she wrote in the caption.
The White House intern-turned-activist has come a long way since her Bill Clinton affair scandal made headlines in the '90s, forcing her into the spotlight, and she's since been able to change the narrative — from cooperating on a biography to getting the Ryan Murphy treatment with FX's "Impeachment: American Crime Story." And in February 2024, she made her modeling debut with fashion house Reformation to lead a voting campaign.
Join us as we take a look back at her best photos over the years…
Gorgeous and glam! Monica Lewinsky opted for a sweet black-and-white Rodarte gown for the Vanity Fair Oscar Party in Los Angeles in March 2023.
Keep reading for more photos of the '90s pop culture figure…
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Here's where it all started! We first met Monica Lewinsky after it was revealed she had an affair with married President Bill Clinton. Their relationship began when Monica was working as an intern at the White House, where they're seen posing for a photograph in this snap from November 1995 — the same month their 16-month affair started.
MORE: See the past 10 presidents when they were young
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A cover girl! Following her affair, Monica Lewinsky became a certified pop culture icon. She sat down with Barbara Walters for a "20/20" interview in 1999 and by 2001, she was covering magazines. She's seen here at a Gotham Magazine party in New York City celebrating her issue in March 2001 wearing a pink sparkly coat.
MORE: Hollywood stars who became politicians
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It would be one of many appearances over the years, but Monica Lewinsky attended her very first Vanity Fair Oscars Party in Los Angeles back in 2001. She wore this spaghetti-strap black gown to the elite bash.
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Look at this trio! Monica Lewinsky was on hand for the launch of pal Andy Cohen's book "The Andy Cohen Diaries" in New York City in 2014 and posed for a photo with the Bravo exec and one of his "Real Housewives" darlings, NeNe Leakes of "The Real Housewives of Atlanta."
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Monica Lewinsky got all bundled up ahead of an event for the Autism Coalition, the "Night of Too Many Stars," in New York City back in February 2003. Later that year, she tried her hand at television hosting on the FOX reality series "Mr. Personality."
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Lady in red! Monica Lewinsky had one of her most memorable fashion moments at the Vanity Fair Oscar Party in Los Angeles back in 2015 in this stunning red short-sleeved gown.
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How '90s is this photo? Monica Lewinsky posed next to New Kids on the Block star Joey McIntyre at the opening of Flow in New York City in April 2002.
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Monica Lewinsky looked pretty in another black dress at an event in June 2014 — the Marie Curie Timeless Party at the Masterpiece London Art Fair. The party took place a month after she penned a well-received essay for Vanity Fair titled "Shame and Survival," which chronicled her life post-scandal.
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By 2002, Monica Lewinsky was able to speak freely after the terms of her immunity agreement ended. That year, she got candid about her experience via an HBO special, "Monica in Black and White," during which she answered questions about her life that were asked by a studio audience. She's seen here that same year at the GQ Men of the Year Awards.
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In 1999, Monica Lewinsky shared her side of the Bill Clinton affair in the biography "Monica's Story," written by Andrew Morton. She reportedly made $500,000 for telling her story.
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Though they may seem like an odd pairing, Alan Cumming and Monica Lewinsky are actually very close friends and have been since 2000. The actor first met Monica at a dinner party that year. They're seen here attending the HBO Golden Globes afterparty in January 2015.
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At this New York City photoshoot in June 2004, Monica Lewinsky rocked a bold leopard-print coat with a teal turtleneck underneath. That same year, Bill Clinton published his autobiography, "My Life," which Monica didn't appreciate. She told DailyMail.com at the time, "He could have made it right with the book, but he hasn't. He is a revisionist of history. He has lied. … I really didn't expect him to go into detail about our relationship. … But if he had and he'd done it honestly, I wouldn't have minded. … I did, though, at least expect him to correct the false statements he made when he was trying to protect the presidency… This was a mutual relationship, mutual on all levels, right from the way it started and all the way through… I don't accept that he had to completely desecrate my character."
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Monica Lewinsky rocked a very different blue dress at the 2018 Vanity Fair Oscar Party in Los Angeles. The former White House intern sported this off-the-shoulder number in a deep blue shade at the flashy Hollywood event.
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Monica Lewinsky kept things pretty casual at Entertainment Weekly's first annual "It List" party at Milk Studios in New York City in June 2002, sporting a sweet peasant blouse, dark jeans and heels.
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In 2021, Monica Lewinsky's life story got the Ryan Murphy treatment on FX's "Impeachment: American Crime Story." Stepping into her shoes on the small screen? Actress Beanie Feldstein, who posed here with the star at a screening of the series that July.
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Monica Lewinsky… bag designer? The famous face is seen here holding a product from her very own line of hand and tote bags, which were sold at Henri Bendel, at an event in New York City in March 2000.
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More fringe! Monica Lewinsky knew her favorite styles — and that included a lot of black dresses and a whole lot of fringe. She's seen here wearing the latter at the premiere of "Knockabout Guys" in New York City in September 2002.
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Monica Lewinsky and Molly Ringwald looked close at "TrevorLIVE LA," an benefit for the Trevor Project in Los Angeles in December 2014. Earlier that year, Monica became an activist against cyberbullying, reflecting on her own experience in the limelight in the '90s.
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In the early '00s, Monica Lewinsky was a fixture at Hollywood events. She's seen here at the premiere of "Austin Powers in Goldmember" in July 2002 rocking a fringe poncho.
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In 2015, Monica Lewinsky was on hand for a big event in New York City — the Tony Awards. The star attended the celebration that June in this dreamy midi-length, off-the-shoulder red dress.
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Ready for an '00s blast from the past? While attending the Manhattan File Magazine party in New York City in December 2000, Monica Lewinsky was spotted chatting with heiress Nicky Hilton.
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Monica Lewinsky showed off a fun twist on the LBD in this tulle trimmed midi-length frock at the Vanity Fair Oscar Party in Los Angeles in February 2017. Red shoes finished off her look on Hollywood's biggest night.
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Monica Lewinsky rubbed elbows with Lena Dunham back in 2018. The duo are seen here at The Hollywood Reporter's Power 100 Women in Entertainment in Los Angeles event that December.
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Monica Lewinsky was all smiles as she attended FX's "Impeachment: American Crime Story" series premiere in Los Angeles in September 2021.
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Monica Lewinsky was on hand for PETA's Party of the Century and Humanitarian Awards in Los Angeles in 1999, arriving in this red sweater set and black trousers.
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In 2005, Monica Lewinsky wanted to get away from the spotlight — so she headed to London. She enrolled in the London School of Economics, graduating with a Master of Science degree. She's seen here 10 years later visiting the Opera Gallery in London in July 2015.
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Monica Lewinsky and actress Brittany Snow looked chummy at the TLC Network Give a Little Awards in Los Angeles in September 2017. Monica wore one of her favorite shades — ruby red — for the occasion.
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To be a fly on the wall for this conversation! Monica Lewinsky posed alongside Amy Schumer at one of her favorite events — the Vanity Fair Oscar Party — in Beverly Hills in March 2022.
