Jennifer Aniston, Then and Now: Pics of the ‘Friends’ Icon Through the Years

View Slideshow
jennifer-aniston-then-now-gallery-18-intro.jpg
Shutterstock

Jennifer Aniston Through the Years


This article originally appeared on Hollywood Life and is syndicated by Cheapism.


Jennifer Aniston was a fresh-faced 25-year-old when she landed the role of Rachel Green on ‘Friends.’ She went on to portray the character for 10 seasons, making her a household name, as well as a very rich woman. By the end of the series, the six leads were pulling down $1 million per episode. Her haircut in seasons 1-2, ‘The Rachel’ led to countless women getting the same multi-length shag. 


After leaving ‘Friends,’ Jennifer stayed mainly in the world of film, with such hits as ‘The Break Up’ and ‘We’re the Millers.’ She even tried her hand at drama with the movie ‘Cake.’ In 2019, Jen turned 50 and looked just as stunning as she did 25 years earlier when she first broke big. She’s now the executive producer and star of the Apple+  drama ‘The Morning Show’ opposite pal Reese Witherspoon. For the role she won her first solo Screen Actor’s Guild Award in 2020, something that moved her beyond belief. It was especially poignant as it was her return to regular series TV for the first time since ‘Friends,’ and it’s a drama, which is something the famed funny lady doesn’t do very often.

jennifer-aniston-then-now-gallery-11.jpg
Tri Star Tv/Kobal/Shutterstock

Jennifer Aniston in a 1992 Portrait

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’.

jennifer-aniston-friends-rex-gallery-01.jpg
Sam Jones/Warner Bros Tv/Bright/Shutterstock
jennifer-aniston-then-now-gallery-10.jpg
Bei/Shutterstock

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.’

jennifer-aniston-then-now-gallery-12.jpg
Globe Photos/mediapunch/Shutterstock
jennifer-aniston-then-now-gallery-13.jpg
Richard Young/Shutterstock
jennifer-aniston-then-now-gallery-14.jpg
Michael Caulfield/AP/Shutterstock
jennifer-aniston-then-now-gallery-16.jpg
Alan Davidson/Shutterstock

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. 

jennifer-aniston-then-now-gallery-15.jpg
Dan Steinberg/BEI/Shutterstock

Brad Pitt and 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. 

jennifer-aniston-then-now-gallery-189.jpg
Shutterstock
jennifer-aniston-then-now-gallery-18.jpg
Matt Baron/BEI/Shutterstock

Jennifer Aniston at 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.

jennifer-aniston-then-now-gallery-17.jpg
Eric Charbonneau/Shutterstock

Jennifer Aniston and Owen Wilson at the ‘Marley & Me’ Premiere

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

jennifer-aniston-then-now-gallery-8.jpg
Jim Smeal/BEI/Shutterstock

Jennifer Aniston Honored With Star on Hollywood Walk of Fame

Jennifer Aniston was honored with a star on the Hollywood Walk of Fame in Los Angeles on Feb. 22, 2012. She wore a pretty print dress for the occasion. 

jennifer-aniston-then-now-gallery-9.jpg
Evan Agostini/Invision/AP/Shutterstock

Justin Theroux and 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 . 

jennifer-aniston-then-now-gallery-6.jpg
Jim Smeal/Shutterstock

Jennifer Aniston at the 2016 Critics’ Choice Awards

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

jennifer-aniston-then-now-gallery-7.jpg
Anthony Harvey/Shutterstock

Jennifer Aniston in a Sexy Black Gown

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.

jennifer-aniston-then-now-gallery-1.jpg
Yoan Valat/EPA/Shutterstock

Jennifer Aniston and 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 U.S. artist Jeff Koons at the Louvre Museum in Paris on April 11, 2017.

jennifer-aniston-then-now-gallery-2.jpg
Rob Latour/Shutterstock

Jennifer Aniston and 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. 

jennifer-aniston-then-now-gallery-3.jpg
Rob Latour/Shutterstock

Jennifer Aniston Rocks a Leather Mini Dress

Jennifer Aniston at the ‘Murder Mystery’ film premiere at Regency Village Theatre in Westwood, California on June 10, 2019. She wore a black Celine leather mini dress. 

jennifer-aniston-then-now-gallery-5.jpg
Gregory Pace/Shutterstock

Jennifer Aniston and Reese Witherspoon Pose Together

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.’

jennifer-aniston-then-now-gallery-4.jpg
John Salangsang/Variety/Shutterstock

Jennifer Aniston in Custom White Dior

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.