What, like it’s hard? Reese Witherspoon has had quite the evolution throughout her career — as an actress, producer and businesswoman.
The southern belle made a splash with her debut film, 1991’s The Man in the Moon, at the ripe age of 14. While she briefly put her acting aspirations on hold following her high school graduation to attend Stanford University, Witherspoon’s calling ultimately won out.
“Growing up in the South, it was very patriarchal. When I applied to Stanford, I was told by a [male] college counselor, ‘You’re never gonna get in, don’t bother. They don’t want you,’” Witherspoon recalled during an October 2015 interview with Glamour. “I said, ‘I’m going to try.’ And I got in! But I wouldn’t be the woman I am if I hadn’t had that conflict to overcome. It has given me an underdog feeling all my life.”
The Tennessee-raised star left college in 1996 to pursue acting full-time, which led to her roles in 1996’s Fear and Freeway. Three years later, Witherspoon cemented herself as a rising star in Hollywood with parts in 1999’s Cruel Intentions and Election.
As the This Means War actress’ career took off, her dating life also heated up. Witherspoon wed Ryan Philippe in June 1999 after meeting at her 21st birthday bash two years prior.
“I don’t know what came over me — maybe the seven Midori sours — but I told [Ryan], ‘I think you’re my birthday present,’” she confessed to Jane magazine in 1998. “He thought it was so flattering, and now that I think about it … how embarrassing!”
The twosome later welcomed daughter Ava and son Deacon in September 1999 and October 2003, respectively. Throughout their marriage, Witherspoon continued to captivate audiences with her work on screen, including 2001’s Legally Blonde, which catapulted her to superstardom.
When the Walk the Line actress won the 2006 Academy Award for her portrayal of June Carter, Philippe was by her side. The pair, however, announced their split later that year after the Shooter alum cheated on Witherspoon with Abbie Cornish. (Philippe later publicly apologized for his affair.)
Witherspoon settled down for a second time in March 2011 when she wed talent agent Jim Toth. The couple share son Tennessee, who was born in September 2012.
Amid all her personal ups and downs, the Daisy Jones & The Six producer pushed forward with her acting and appeared in hit after hit. The Shine on With Reese star, however, didn’t stop at acting, she has added business owner and entrepreneur to her resume over the years.
In addition to launching her clothing brand, Draper James, she founded the media company Hello Sunshine and has stepped behind the camera as a producer on multiple projects. Witherspoon revealed in April 2019 that much of her success has come from leaning into her wisdom.
“I have a point of view because I’ve been on this planet for 43 years, and I didn’t feel that same way when I was 25. I didn’t have the same things to say,” the Reese’s Book Club founder told Allure at the time. “I’m 43 and I’ve had a whole bunch of experiences, and I can speak with a thoughtfulness about the changes I’d like to see in the world, and I just feel like I earned that gray hair and my fine lines. I like ’em. I so prefer 43 to 25.”
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Scroll down to see Witherspoon’s evolution from teenage actress to multi-hyphenate: