See Her Transformation In Photos – Hollywood Life

Reese Witherspoon Then & Now: See the Star's Transformation Over the Years — Image Credit: Getty Images

Happy birthday, Reese Witherspoon!

On March 22, the actress turned 49! To celebrate the occasion, we’re taking a look back at her remarkable transformation throughout her brilliant career. Reese began acting in the mid-’90s as a teenager, but her big break came in her early 20s with a starring role in the 1999 drama Cruel Intentions. From there, she capitalized on her newfound fame, proving she could handle both comedy and drama with her role in the 1999 satirical film Election.

Reese continued to land roles in films like American Psycho and even made a memorable guest appearance on the NBC sitcom Friends, where she played Rachel Green’s (Jennifer Aniston) sister. However, Reese’s star soared to new heights when she starred as Elle Woods in the 2001 hit Legally Blonde. The role became iconic, and Reese became synonymous with the beloved comedy. She reprised her role in 2003 for the sequel, Legally Blonde 2: Red, White & Blonde, a film she also produced.

**Reese Witherspoon in the 1991 film ‘The Man In The Moon’ [Shutterstock].**

Two years after the success of Legally Blonde 2, Reese cemented her place in history with her transformative performance as June Carter Cash in the critically acclaimed film Walk the Line. Her portrayal earned her rave reviews and led to her winning her very first Academy Award for Best Performance by an Actress in a Leading Role. From there, Reese continued to use her platform to spotlight remarkable work, producing films like Gone Girl and starring in both comedies and dramas with equal finesse.

Years after making her big-screen debut, Reese made a major leap to television, teaming up with friend and collaborator Nicole Kidman to bring the novel Big Little Lies to HBO. The women received immense praise for their work both in front of and behind the camera, delivering a vital story to audiences. Reese has since continued to empower and amplify incredible stories as a producer.

Reese Witherspoon arrives at the 26th annual Screen Actors Guild Awards at the Shrine Auditorium & Expo Hall in Los Angeles on January 19, 2020 [Shutterstock].

Reese has starred in the mini-series Little Fires Everywhere, where she also served as one of the series’ producers. During this time, she earned her second Oscar nomination for her work in the 2014 film Wild. Reese then went on to star in the Apple TV+ series The Morning Show, where she reunites with Friends co-star Jennifer.

In 2023, Reese executive produced My Kind of Country, a country music competition show, alongside Kacey Musgraves. She also starred opposite Ashton Kutcher in the romantic comedy Your Place or Mine, which was released on Netflix. In 2025, she starred in and produced the romantic comedy You’re Cordially Invited for Amazon Prime Video, alongside Will Ferrell.

As for her personal life, Reese shares daughter Ava Elizabeth Phillippe and son Deacon Reese Phillippe with ex-husband Ryan Phillippe. She later married talent agent Jim Toth in 2011, and the couple welcomed their son, Tennessee James Toth, in September 2012. On March 24, 2023, just days before their 12-year wedding anniversary, Reese and Jim announced they were divorcing. A year after settling her divorce in August 2023, Reese was seen with private equity financier Oliver Haarmann on several occasions, and it was later confirmed by multiple sources that they were dating.

Reese has achieved so much in both her career and personal life, and you can view more pictures of her here.

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1 1999

2 Reese & Her Kids 2010

3 2024

4 Reese & Her Kids 2024