Reese Witherspoon's Life in Photos (2024)

Reese Witherspoon has been gracing our screens since she was just 14 years old, and over the years, she’s given us unforgettable performances in hits like Legally Blonde and Sweet Home Alabama. Today, the child star-turned-powerhouse producer is one of the highest-paid actresses in Hollywood, and she runs an über-popular book club and clothing line on the side (nbd). But she didn't get there without a lot of hard work along the way. Ahead, take a look at the evolution of the Southern belle's life and career over the years.

Witherspoon landed her first major role in Robert Mulligan's The Man in the Moon. She played one of the three main characters, alongside Jason London and Emily Warfield, and was just 14 years old when she appeared in the film.

The actress opted for a daisy tank top, black cowboy boots, and a *very* '90s updo for her first movie premiere. Here, she poses with her costars, Jason London and Emily Warfield.

A 15-year-old Witherspoon poses in Deauville, France at the Deauville American Film Festival.

In 1993, Witherspoon appeared in the TV miniseries, Return to Lonesome Dove, as well as two movies, A Far Off Place and Jack the Bear.

While emerging onto the scene in the early '90s, Witherspoon was romantically linked to up-and-coming actor Chris O'Donnell.

There were also rumors that Witherspoon dated actor Stephen Dorff in 1993 and 1994, but the actress denies that they were ever romantically linked.

Here, Witherspoon is seen at the Waterworld premiere. During this time in her, her star was rising—and she even almost got cast as Cher in Clueless.

In 1996, Witherspoon appeared in two films, Fear, alongside Mark Wahlberg, and Freeway, which was a hit at the Sundance Film Festival.

Witherspoon at the Hollywood premiere of Two Days in the Valley at the Mann Village Theatre in a red leather jacket and pin striped pants.

To be honest, we hardly recognize Witherspoon here. But, hey, she was 20 and clearly in a little bit of a rebellious phase.

Another day, another premiere. This one was for Nowhere and Witherspoon rocked just about every trend from the '90s she could: mini buns, chokers, and spaghetti straps.

Witherspoon looked the part of movie star in an all black ensemble at the Vanity Fair Oscars After-Party.

By 1998, Witherspoon was being considered for bigger and bigger roles, including a role alongside Paul Newman and Susan Sarandon in the thriller Twilight.

On the set of her next big film, Cruel Intentions, Witherspoon and Ryan Phillippe began dating and were soon Hollywood's "It" couple. The two met before working together, at Reese's 21st birthday party. "I don't know what came over me—maybe the seven Midori sours—but I told [Phillippe], 'I think you're my birthday present. He thought it was so flattering, and now that I think about it...how embarrassing!" Witherspoon told JANE Magazine in 1998.

Witherspoon starred in Cruel Intentions, a modern adaptation of the french novel Les Liaisons Dangereuses, alongside big names like Sarah Michelle Gellar and Selma Blair, as well as Phillippe. It was her biggest role to date.

After one year of dating, and while still promoting the film that brought them together, the young couple said "I do" in a private ceremony in Charleston, South Carolina in June 1999.

A few months after their wedding, the newlyweds were spotted at a Hole concert at The Palace in Los Angeles on a date night.

Witherspoon and Phillippe welcomed their first child together, daughter Ava Phillippe, three months after their wedding.

Witherspoon's professional career took off in 2000. She received her first Golden Globe nomination for her role in Election and appeared alongside Christian Bale in American Psycho.

The actress is seen with her husband and one year old daughter, Ava, on set while shooting scenes for Legally Blonde in 2000.