Jennifer Aniston Then & Now: Photos Of The ‘Friends’ Icon From Her First Roles To Today

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Jennifer Aniston Through The Years

Jennifer Aniston Through The Years — Jennifer Aniston, born Feb 11, 1969, is one of TV’s most beloved actresses. She initially rose to fame as Rachel Green in the hit series Friends, where she slayed for 10 seasons, earning $1 million per episode and becoming a household name.

Almost instantly, Jennifer became a style icon. “The Rachel” haircut made serious waves, with millions copying the look upon its debut.

Post Friends, Jennifer dominated film with hits like The Break Up and We’re the Millers, even trying her hand at drama in Cake. Now, as the exec producer and star of The Morning Show opposite Reese Witherspoon, Jennifer earned her first solo Screen Actor’s Guild Award in 2020.

From Rachel to Hollywood power player, Miss Aniston’s evolution is a thing of beauty. Check out the photo gallery for her best looks from the start.

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Jennifer Aniston In 1992

Jennifer Aniston In 1992 — Jennifer Aniston in a 1992 portrait for the TV show ‘The Edge.’ She was fresh-faced and young in the pic, ahead of her breakout role on ‘Friends’. She got involved in Hollywood at an early age as the daughter of actor John Aniston.

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Jennifer Aniston In A 1996 Promo Shot For ‘Friends’

Jennifer Aniston In A 1996 Promo Shot For ‘Friends’ — Jennifer Aniston in a 1996 promo shot for ‘Friends.’ She looked gorgeous in a black spaghetti strap tank and straightened hair.

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Jennifer Aniston At The 1995 GLAAD Media Awards

Jennifer Aniston At The 1995 GLAAD Media Awards — Jennifer Aniston attends the 1995 GLAAD Media Awards. At the time she still had her infamous ‘Rachel’ hairstyle from ‘Friends.’

Rachel was less than thrilled while talking about her iconic “Rachel” hairstyle in a 2011 photoshoot with ‘Allure’. Talking about her longtime stylist Chris McMillan, she said, “I love Chris, and he’s the bane of my existence at the same time because he started that damn Rachel, which was not my best look. How do I say this? I think it was the ugliest haircut I’ve ever seen.”

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Jennifer Aniston Strikes A Pose

Jennifer Aniston Strikes A Pose — Jennifer Aniston rocking her ‘Rachel’ hairstyle from ‘Friends’ around 1994-1995 in a promo shot. She posed with her hair styled in a barrette for the shoot.

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Brad Pitt & Jennifer Aniston At The 2000 Oscars

Brad Pitt & Jennifer Aniston At The 2000 Oscars — Brad Pitt and Jennifer Aniston attend the 2000 Vanity Fair Oscars Party. At the time the pair were engaged and went on to marry on July 29, 2000. While they divorced in 2005, the couple went on to stay friends. During a 2021 appearance on ‘The Howard Stern Show’, she told the shock-jock, “Brad and I are buddies. We’re friends.”

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Courteney Cox, Jennifer Aniston & Lisa Kudrow

Courteney Cox, Jennifer Aniston & Lisa Kudrow — ‘Friends’ stars Courteney Cox, left, Jennifer Aniston, center, and Lisa Kudrow arrive to host the 10th annual Fire & Ice Ball in Beverly Hills. The gala event raises funds for Revlon/UCLA Women’s Cancer research program

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Jennifer Aniston At The ‘Along Came Polly’ premiere

Jennifer Aniston At The ‘Along Came Polly’ premiere — Jennifer Aniston at the ‘Along Came Polly’ UK premiere at the Empire Leicester Square on Feb. 18, 2004. She looked ravishing in red for the debut of the rom-com, which also starred Ben Stiller.

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Brad Pitt & Jennifer Aniston At The 2004 Emmy Awards

Brad Pitt & Jennifer Aniston At The 2004 Emmy Awards — Married couple Brad Pitt and Jennifer Aniston at the 56th Annual Emmy Awards in Los Angeles on Sept. 19, 2004. Sadly the pair would separate five months later in Jan. 2005.

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Jennifer Aniston & John Mayer at the 2009 Oscars

Jennifer Aniston & John Mayer at the 2009 Oscars — Jennifer Aniston and John Mayer attend the 81st Annual Academy Awards Vanity Fair Party in Los Angeles on Feb. 22, 2009. Jen looked stunning in her strapless dress, while John was handsome in a tux. Their romance was short-lived.

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Jennifer Aniston Attends The ‘He’s Just Not That Into You’ Premiere

Jennifer Aniston Attends The ‘He’s Just Not That Into You’ Premiere — Jennifer Aniston attends the ‘He’s Just Not That Into You’ film premiere At The Grauman’s Chinese Theatre In Los Angeles on Feb. 2, 2009. At the time she was dating singer John Mayer.

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Jennifer Aniston & Owen Wilson At The ‘Marley & Me’ Premiere

Jennifer Aniston & Owen Wilson At The ‘Marley & Me’ Premiere — Jennifer Aniston and Owen Wilson at 20th Century Fox Premiere of ‘Marley & Me’ on December 11, 2008 at Mann’s Village Theatre in Westwood, California. The co-stars looked quite friendly, but there was no romance.

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Jennifer Aniston Honored with Star on Hollywood Walk Of Fame

Jennifer Aniston Honored with Star on Hollywood Walk Of Fame — Jennifer Aniston honored with Star on The Hollywood Walk Of Fame in Los on Feb. 22, 2012. She wore a pretty print dress for the occasion.

Her friend and ‘Go With It’ co-star Adam Sandler presented the honor, telling onlookers when Jen was young, “She prayed for three things: To have everyone in the entire world be fascinated with her haircut, to one day star in a movie about an evil leprechaun who kills people, and most importantly, receive a star on the prestigious Hollywood Walk of Fame. Well today, Jennifer, the trifecta is here.”

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Justin Theroux & Jennifer Aniston At The 2015 Oscars

Justin Theroux & Jennifer Aniston At The 2015 Oscars — Justin Theroux and Jennifer Aniston arrive at the 2015 Vanity Fair Oscar Party, in Beverly Hills following the 87th Academy Awards. The couple was already engaged at this point, and would wed later that year. By 2017, however, the relationship had run its course.

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Jennifer Aniston At The 2016 Critics’ Choice Awards

Jennifer Aniston At The 2016 Critics’ Choice Awards — Jennifer Aniston looks stuning at the 21st Annual Critics’ Choice Awards in Los Angeles on Jan. 17, 2016. She wore a seafoam blue Saint Laurent gown.

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Jennifer Aniston At The 2017 Vanity Fair Oscar Party

Jennifer Aniston At The 2017 Vanity Fair Oscar Party — Jennifer Aniston looks super sexy while attending the Vanity Fair Oscar party in Feb. 2017. The dress featured a thigh-high leg slit and a low-cut neckline.

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Jennifer Aniston & Justin Theroux in Paris

Jennifer Aniston & Justin Theroux in Paris — Actress Jennifer Aniston and actor Justin Theroux arrive at the launch party by French fashion house Louis Vuitton. It was promoting a new line of bags and accessories created by US artist Jeff Koons at the Louvre Museum in Paris, France on Apr. 11, 2017. They split later that year.

Justin reflected on the relationship in a 2021 interview with ‘Esquire’, assuring people there was nothing earth-shattering about their break-up. “Like it or not, we didn’t have that dramatic split, and we love each other,” he said. “I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship. It would be a loss if we weren’t in contact, for me personally.”

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Jennifer Aniston & Courteney Cox in Black Gowns

Jennifer Aniston & Courteney Cox in Black Gowns — Besties Jennifer Aniston and Courteney Cox arrive at the AFI Life Achievement Award Gala in Los Angeles on June 7, 2018. Both donned black gowns. The event honored George Clooney.

Jen gushed about her co-star and close friend in 2014, telling ‘More’ magazine, “There’s absolutely no judgment in Court. You’ll never feel scolded. She’s extremely fair, ridiculously loyal and fiercely loving. I’ve slept in her guest bedroom a lot. Without giving away too much of my private stuff, all I can say is she’s been there for me through thick and thin.”

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Jennifer Aniston Rocks A Leather Mini Dress

Jennifer Aniston Rocks A Leather Mini Dress — Jennifer Aniston at the ‘Murder Mystery’ film premiere, Regency Village Theatre in Westwood, CA on June 10, 2019. She wore a black Celine leather mini-dress.

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Jennifer Aniston & Reese Witherspoon

Jennifer Aniston & Reese Witherspoon — Jennifer Aniston and Reese Witherspoon pose on the red carpet. The pair were glued at the hip during the 2020 awards season for ‘The Morning Show.’

While the duo plays rivals on the show, Jennifer said she loves to spar with her pal for the cameras. “It’s always fun to fight with Reese,” she told Jimmy Kimmel in Sep. 2021, “because she’s such a sweet burst of sunshine that she’s, you know, not someone you wanna go scream your head off to. And I usually always end up bursting into laughter at some point. It’s just too hard to be that mad with each other. But we do it.”

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Jennifer Aniston Wins A SAG Award

Jennifer Aniston Wins A SAG Award — Jennifer Aniston wins Outstanding Performance by a Female Actor in a Drama Series for ‘The Morning Show’ at the 26th Annual Screen Actors Guild Awards on Jan. 19, 2020. She wore a custom white Dior gown.

Talking about the role during her acceptance speech, she said, “Boy, did we get to dive deep into our own experiences and our own history and really be able to breathe life into these extraordinary characters.” She then quipped, “Who knew that emotional breakdowns felt that good? It really was like, seven months of therapy covering about 20 years of work. So thank you for watching that.”

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Jennifer Aniston In 2021

Jennifer Aniston In 2021 — Jennifer Aniston is elegant in a black and white shot promoting her own haircare brand LolaVie in 2021. Through the years, Jennifer has enjoyed tons of high-profile sponsorships with brands like Smart Water, Aveeno, Vital Protiens, and more

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Jennifer Aniston At The Premiere Of ‘The Morning Show’ Season 2

Jennifer Aniston At The Premiere Of ‘The Morning Show’ Season 2 — Jennifer Aniston looked radiant during an FYC Emmy screening and Q&A for The Morning Show’s second season held Jun. 11, 2022. Her floral dress was a light yellow, cut on the bias, and with an asymmetrical neckline.

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Jennifer Aniston Films ‘The Morning Show’

Jennifer Aniston Films ‘The Morning Show’ — In character! Jennifer Aniston looked sharp in specs, a cropped jacket, and jeans while on location filming The Morning Show on Sep. 26, 2022. The cast and crew gathered for a scene at New York’s Mercer Hotel.

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