Relive Reese Witherspoon's Last 25 Years in Hollywood, in Photos

1996

Though roles in movies like Jack the Bear and The Man in the Moon would come before it, Witherspoon's breakout role was arguably in Fear, a thriller about a teen romance gone wrong.

For the most terrifying flick from your adolescence, check out The Scariest Movie That Came Out the Year You Graduated.

1997

Witherspoon had no major projects hit in 1997, but the actor was still out and about in Hollywood. Here she is at the premiere of the Jim Carrey comedy Liar, Liar.

1998

In 1998, she was also at the theaters with Twilight (not the vampire flick) and Overnight Delivery. But Witherspoon's most iconic work that year was in Pleasantville, the drama about teen siblings who find themselves trapped in the aw-shucks world of their favorite black-and-white TV show.

For series that had audiences fully obsessed, check out The 50 Most Popular TV Shows of All Time.

1999

Witherspoon helped make two indelible marks on pop culture in 1999. First, she costarred in Cruel Intentions (above), as an innocent girl who becomes a pawn in the game of two bored, rich step-siblings, and Election, a dark comedy in which she plays an overly ambitious student who'll do anything to succeed. She fell in love with costar Ryan Phillippe on the former, and they married the same year their movie came out.

2000

In 2000, Witherspoon appeared in the film adaptation of American Psycho, the Adam Sandler flick Little Nicky, did some voice work on King of the Hill, and even founded her production company, Type A. But Friends fans will most fondly remember that year as the one where she guested as one of Rachel's still-spoiled sisters, Jill Green.

To see how Jill stacks up against the rest of the gang, check out Every Major "Friends" Character, Ranked From Worst to Best.

2001

Ah, 2001. With the rest of the Legally Blonde cast, Witherspoon helped make the world a little brighter and a little pinker.

2002

Witherspoon went period in a funny adaptation of The Importance of Being Earnest in 2002; she also played a high-powered city girl falling back in love with the town—and the man—she left behind in Sweet Home Alabama.

To find out which rom-com movie buffs love the most, check out This Is the Best Romantic Comedy of All Time, According to Critics.

2003

Legally Blonde 2 isn't as much of a delight as its predecessor, but hey: we'll take all the Elle Woods we can get.

2004

Witherspoon played legendary literary anti-hero Becky Sharp in Mira Nair's colorful adaptation of Vanity Fair. By the time this premiere rolled around, she and Phillippe had welcomed two children.

2005

Witherspoon trained to sing and play the auto-harp in her role as June Carter Cash in Walk the Line, the Johnny Cash biopic that focuses on their love affair. On the rom-com front, there was Just Like Heaven, a fairly dark entry into the genre, with Mark Ruffalo.

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2006

On screen, Witherspoon had a bit part in the fantasy rom-com Penelope, which was also her second project as a producer (the Legally Blonde sequel was the first). In 2006, she also collected her Oscar for her role in Walk the Line, and sadly saw the end of her marriage to Phillippe.

2007

In 2007, Witherspoon starred in Rendition, a terrorism drama that didn't go over well with critics or audiences.

2008

Back to comedies in 2008! Witherspoon teamed up with Vince Vaughn��for the holiday romp Four Christmases, about a couple who ends up splitting the holiday season among their four divorced parents.

2009

Come 2009, Witherspoon was again lending her voice to a project: this time, it was the animated sci-fi flick Monsters vs. Aliens.

2010

In 2010, she starred opposite Owen Wilson and Paul Rudd in the James L. Brooks relationship comedy How Do You Know. She also apparently had the answer to that question, as she got engaged to agent Jim Toth and married him the next year.

2011

Maybe you and your book club went to see Witherspoon's biggest 2011 venture. She got up close and personal with Robert Pattinson and some circus animals in the adaptation of the bestseller Water for Elephants.

2012

Another love triangle flick, this one with more guns and spy tech. In This Means War, Witherspoon played the object of the affections of two super spies (Chris Pine and Tom Hardy) who also happen to be best friends. She also appeared in the Matthew McConaughey drama Mud.

2013

While it hit festivals in 2013, Witherspoon's sole movie for that year, Devil's Knot, wasn't released until 2014. The drama about the wrongly convicted West Memphis Three flew under the radar even then.

2014

Witherspoon was nominated for another Best Actress Academy Award for Wild, the adaptation of Cheryl Strayed's brutal and emotional memoir. She also produced it, which made her more of a development force to be reckoned with in Hollywood.

2015

The only 2015 movie Witherspoon starred in was the lukewarm Hot Pursuit, costarring Sofia Vergara. But, in better news, she was honored at the American Cinematheque Awards that year, bringing kids Ava and Deacon as her dates.

2016

In 2016, Witherspoon put her vocal chops to use again in the musical comedy Sing, in which she played a pig named Rosita.

2017

The Monterey Five made their mark on HBO in 2017. Witherspoon produced and also starred alongside a powerhouse cast of women on Big Little Lies, the hugely buzzy (and Emmy-winning) series adaptation of the Liane Moriarty novel. Meanwhile, on the big screen, she played a single mom dealing with a young admirer in the rom-com Home Again.

2018

In 2018, Witherspoon got a glittery fantasy makeover along with Oprah Winfrey and Mindy Kaling to play Mrs. Whatsit in the dazzling film version of the classic children's novel A Wrinkle in Time.

2019

Another hit series for Witherspoon as a producer and an actor. The Morning Show was one of the shows on the first slate of Apple TV originals. It's already been renewed for Season 2.

2020

Somehow Witherspoon found the time to gift viewers another juicy TV drama based on a much-talked-about book. She helped bring Little Fires Everywhere to streaming and also starred opposite Scandal alum Kerry Washington.