Reese Witherspoon Through the Years: Photos

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.

Witherspoon left college in 1996 to pursue acting full-time, which led to her roles in 1999’s Cruel Intentions and Election. She became a mega star after starring in hits like 2001’s Legally Blonde and Walk the Line, which earned the actress her first Academy Award in 2006.

As Witherspoon’s career took off, her dating life also heated up. She married Ryan Phillippe in June 1999 and the pair welcomed two children, Ava and Deacon. Witherspoon and Phillippe split in 2006 and the actress later married talent agent Jim Toth in 2011. The couple welcomed son Tennessee in 2012 and a decade later divorced.

Related: Reese Witherspoon’s Dating History: Ryan Phillippe, Jim Toth and More

What, like it’s hard? Reese Witherspoon has romanced multiple A-listers throughout her time in the spotlight, but not all of her relationships have had happily ever afters. After meeting Ryan Phillippe at her 21st birthday party in 1997, the twosome starred as love interests in 1999’s Cruel Intentions. The sexy flick may have made fans […]

Witherspoon has remained a heavy hitter in Hollywood thanks to her acting, production chops and business acumen.

Scroll down to see Witherspoon’s evolution from teenage actress to multi-hyphenate: