Over the years, Reese Witherspoon has become a beloved figure in Hollywood cinema. Her range for comedy knows no bounds, and her dramas never fall short on expectations. Witherspoon’s first performance was in a 1991 film called The Man in the Moon. She then starred in several subsequent films that put her on the map as a budding young actress. She was the female lead in the 1996 thriller, Fear and was amongst the ensemble cast in Cruel Intentions, where she played a naive student who inevitably falls for the resident bad seed. Witherspoon went on to star in American Psycho, playing Patrick Bateman’s money-hungry fiancée.
With over a dozen films under her belt, Witherspoon landed the role as Elle Woods in the 2001 classic comedy Legally Blonde, a performance that would become her breakout role. From here, Witherspoon became a romantic comedy icon. She had her own talk show, has her infamous book club, Reese’s Book Club, produced successful movies and TV shows, and will be a part of the third Legally Blonde movie. Here’s a look back at Reese Witherspoon's best rom-com movies to date.
5 Home Again
Home Again follows the story of a mother named Alice who is recently separated from her husband. With the recent revelation of turning 40, she makes the decision to move back to Los Angeles, with her daughters, into her father's old home in order to be closer to her mother. Briefly after her return, Alice meets three aspiring filmmakers who are in Los Angeles to pitch their film to a major producer. Somehow in the mix of things, they end up spending the night at Alice's home, and after flattering her mother with compliments about the film success of her husband, Alice's mother offers them the guest house. The three young men form a bond with Alice and quickly become apart from her family dynamic, helping her acclimate in different ways to her new life. However, all goes haywire when Alice's ex-husband shows up at her door, confronting the unorthodox living situation. Home Again is a comedy that provides strange stakes, and unconventional laughs as well as a typically charming performance by Reese Witherspoon.
4 Sweet Home Alabama
A successful New York City fashion designer hides her Southern roots and goes by an alias to protect her new-found social status. Melanie is set to be engaged to her handsome, wealthy boyfriend Andrew, but must return to her home in Alabama to finalize a divorce from her previous life. While home, mayhem ensues as Melanie reunites with old friends and confronts her ex, Jake, who is still refusing to sign the divorce papers. To add another layer of stress to the situation, Andrew's mother sends her assistant to gather information on Melanie to expose her and prove that she is not worthy of her son. Sweet Home Alabama is comedy whose core purpose is to flip the switch on the common saying "you can never go home again" by proving that you absolutely can, and your past will always find you.
3 Four Christmases
Four Christmases easily became a seasonal must-watch during the holidays. The comedic energy between Reese Witherspoon and Vince Vaughn is uncanny. Young couple Brad and Kate avoid going home for the holidays every year and take a vacation instead. Traumatized by their families, the two makeup excuses every year to skip out on the festivities — until one Christmas when their flight is canceled, and they are surprised by a news station conducting interviews. Their families quickly become aware of their scheme, and the couple is forced to return home for the holidays and attend four separate Christmas events. During their time home, Kate realizes that she may want kids, which briefly threatens their relationship, until Brad comes around to the idea, tying a perfect bow on this Christmas Rom-Com.
2 Pleasantville
Before Reese Witherspoon became Elle Woods, and Tobey Maguire started slinging webs as Spider-Man, the two appeared as siblings in the 1998 film Pleasantville. Witherspoon stars as Jennifer, a promiscuous teen who is headed for a troubled life, while Maguire is David, the exact opposite. When David and Jennifer get sucked into their television set after given a remote by a questionable TV repair man, the two must learn to adapt to the town dynamic of Pleasantville that is reminiscent of the 1960s sitcom, Leave It to Beaver. However, Jennifer can't contain herself in this literal black and white world, and introduces the boys of Pleasantville to colors they've never seen before. Although the film teeters between a comedy, romance, and fantasy, Pleasantville explores a genre all its own.
1 Legally Blonde
Falling at number one hundred and nine out of one hundred and fifty on the Rotten Tomatoes list of essential comedies, Legally Blonde is a truly a must-watch. Reese Witherspoon's portrayal of Elle Woods is absolutely charming, and the character herself has become a comedic icon and one of cinema's most empowering female characters. Legally Blonde was Witherspoon's breakout role and is her legacy to ultimate stardom. The film follows a wealthy sorority college student who, after being dumped by her boyfriend for being too blonde, follows him to Harvard in an attempt to win him back and win the engagement ring. However, in her time at Harvard, Elle realizes that her breakup was a blessing, and her true calling is to be a successful lawyer, proving to herself and everyone else that she was smart enough all along. Legally Blonde deserves its place among the great comedies to come out of the 2000s.