Reese Witherspoon is arguably one of the biggest movie stars in the world and most definitely America's Sweetheart. She's been in so many great movies that it's hard to keep track, but in honor of the 20th anniversary of "Election" — her high school comedy film that hit theaters on May 7, 1999 — we've decided to rank some of her most memorable flicks. Keep reading to see which one is our fave…
19. "Hot Pursuit"
Sofia Vergara and Reese Witherspoon as two kick-butt action heroines should be entertaining, in theory. Unfortunately, "Hot Pursuit" just didn't live up to the hype. The 2015 film, which stars Reese as a straight-laced cop and Sofia as her wisecracking witness, lacked the humor and chemistry needed for it to work.
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18. "How Do You Know"
"How Do You Know" has an all-star cast (Reese Witherspoon, Paul Rudd, Owen Wilson, and Jack Nicholson) and a super-cute story, but unfortunately, it wasn't enough to make this movie enjoyable. The 2010 rom-com, which was critiqued for its writing and directing, was a box office bomb that grossed only $49 million against $100 million budget. Reese, however, was adorably likable in the flick!
17. "This Means War"
"This Means War" was an action-comedy that never quite worked, despite a stellar cast. A woman (Reese Witherspoon) dating two spies — played by Tom Hardy and Chris Pine — sounds like a dream come true, but the movie turned out to be one of her most underperforming cinematic attempts.
16. "A Wrinkle in Time"
"A Wrinkle in Time" is fun female empowerment movie that audiences and critics enjoyed — somewhat. The 2018 sci-fi flick, which stars Reese Witherspoon as an astral being from the planet Uriel, has a celebrated message of diversity, but its heavy emphasis on CGI and major plot holes hurt the film's standing on our list.
15. "Four Christmases"
"Four Christmases" paired Reese Witherspoon with Vince Vaughn in a run-of-the-mill holiday comedy about a couple who has to visit all four of their divorced parents in one day. While it might seem like a great idea, the execution here wasn't the strongest and it certainly will not go down as one of their bests. Bah, humbug!
14. "Inherent Vice"
"What is going on here?" is what you'll ask yourself as you watch director Paul Thomas Anderson's take on the famous Thomas Pynchon novel "Inherent Vice." Reese Witherspoon is only in the movie for a handful of moments as Deputy District Attorney Penny Kimball, but they are memorable ones. While this one certainly cannot be blamed on Reese, the high-concept drug-fueled mystery left viewers with more questions than answers. Though it did reunite Reese with her "Walk The Line" co-star Joaquin Phoenix, so there's that!
13. "The Man in the Moon"
One of Reese Witherspoon's first forays into major studio pictures, the rural Louisiana-set "The Man in the Moon," helped introduce the world to the future mega-star. The movie is heavy but has a lot of heart and gave us glimpses of the talent and charisma we have come to expect from a Reese performance later in her career.
12. "The Importance of Being Earnest"
"The Importance of Being Earnest" marked a big shift in Reese Witherspoon's career as it paired her with heartthrobs Colin Firth and Rupert Everett and legend Dame Judi Dench in an English period piece. The movie was by no means perfect, but her performance in Oscar Wilde's dizzying tale of deception and romance proved that Reese was finally in league with the big boys. And she got to be funny as well as try out that English accent she has come to love!
11. "Legally Blonde 2: Red, White & Blonde"
More Elle Woods? Yes, please! Reese Witherspoon dazzled as Elle Woods in 2003's "Legally Blonde 2: Red, White & Blonde." The sequel, which follows Elle as she fights for animal rights in Washington, D.C., may not have been as fun as the original, but we still couldn't get enough of our favorite blonde lawyer.
10. "Vanity Fair"
More accents! "Vanity Fair" placed Reese Witherspoon in the socially stagnant world of British high society. James Purefoy starred alongside Reese in this pointed take on how class affected British life and women's role in it. It also marked one of Reese's early attempts at carrying a major movie.
9. "Water for Elephants"
Heartthrob Robert Pattinson co-starred with Reese Witherspoon in "Water for Elephants," a 1930s circus-set love story. Rob's character plays a veterinarian who falls in love with Reese's character — she's married to the ringmaster — and drama ensues. If you remember, Rob played Reese's son in "Vanity Fair," so this pairing was a little awkward to say the least.
Tobey Maguire and Reese Witherspoon starred together in "Pleasantville," a dreamy movie about siblings who are transported back to the 1950s and inadvertently add color to a changing world. It's one of the most interesting movies on this list as we start transitioning into some of her more iconic performances.
7. "American Psycho"
"American Psycho" is arguably one of the most iconic movies of the early aughts. Christian Bale's creepy performance as sociopath Patrick Bateman is legendary, but Reese Witherspoon steals the show in the couple of scenes she appears in as his wealthy, unaware girlfriend who just wants to lock her boyfriend down.
"Wild," based on the novel by Cheryl Strayed, is one of Reese Witherspoon's most ambitious performances. It earned her an Oscar nomination for her work playing a recovering drug addict who embarks on a 1,000-mile hike to recover from a personal tragedy. Reese also served as a producer on this movie, proving she is a force to be reckoned with in Hollywood.
5. "Sweet Home Alabama"
Can you think of anyone who has seen "Sweet Home Alabama" and not fallen in love with it? Reese Witherspoon starred as a big-city fashion designer who wants to marry the son of New York City's mayor (played by Patrick Dempsey) but first must go home and finalize her divorce from her charming childhood friend (played by Josh Lucas). A great reminder that Reese is just a Southern girl underneath it all.
4. "Walk the Line"
Not only was "Walk the Line" a terrific movie, but it cemented Reese Witherspoon as a box-office queen and a serious actress — with a surprisingly strong and beautiful voice. In fact, the biopic about the late Johnny Cash (played by Joaquin Phoenix) earned Reese her first Oscar and got Hollywood to start taking her more seriously. June Carter Cash would be proud!
Reese Witherspoon nailed the role of Tracy Flick, the obsessive-compulsive Type-A overachiever at the center of "Election." The Alexander Payne-directed comedy showed the world how convincing Reese could be in such an intense role.
2. "Cruel Intentions"
"Cruel Intentions," the ultimate '90s movie, captured the sexiness and pretentious wealth of Upper East Side teenagers long before "Gossip Girl" ever existed. Reese Witherspoon got to play the "good girl who gets corrupted" role opposite Sarah Michelle Gellar and Ryan Phillippe. The movie still holds up to this day, plus we all got to watch as Reese and Ryan fell in love right before our eyes. Also… "BITTER SWEET SYMPHONY."
1. "Legally Blonde"
"Whoever said orange is the new pink was SERIOUSLY disturbed." Reese Witherspoon's best movie is, without a doubt, "Legally Blonde." Her game-changing portrayal of sorority president-turned-Harvard Law School student Elle Woods will go down in history as a career-defining performance that is still oft-quoted today. We will never tire of overcoming obstacles and saying, "What? Like it's hard?" We will ALWAYS love this classic movie!