Top 10 Reese Witherspoon Movies of All Time

We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 Reese Witherspoon movies of all time. Don’t forget to check out other lists throughout Thought for Your Penny.

10. Cruel Intentions (1999) 49% at Rotten Tomatoes

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Kathryn and Sebastian are manipulative step-siblings who always get what they want. They make a bet on whether Sebastian can sleep with the headmaster’s daughter, and things quickly get dark.

Rating: R
Director: Roger Kumble
Starring: Reese Witherspoon, Sarah Michelle Gellar, Ryan Phillippe

9. Four Christmases (2008) 24% at Rotten Tomatoes

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Brad and Kate typically avoid family on the holidays until they’re caught on the news heading to Fiji and must visit all four of their divorced parents. Now their relationship must weather four storms it may not be strong enough to handle.

Rating: PG-13
Director: Seth Gordon
Starring: Reese Witherspoon, Vince Vaughn, Mary Steenburgen

8. Just Like Heaven (2005) 55% at Rotten Tomatoes

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Elizabeth Masterson gave up her personal life to focus on her medical career. She ends up in a coma after a car accident, and her spirit haunts her apartment, which is now occupied by a lonely architect who’s falling in love with her.

Rating: PG-13
Director: Mark Waters
Starring: Reese Witherspoon, Mark Ruffalo, Donal Logue

7. Mud (2012) 97% at Rotten Tomatoes

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Two teenagers come across Mud, a fugitive who’s being pursued by bounty hunters. Now they must help him escape to reunite with the woman he loves.

Rating: PG-13
Director: Jeff Nichols
Starring: Reese Witherspoon, Matthew McConaughey, Tye Sheridan

6. Freeway (1996) 76% at Rotten Tomatoes

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A juvenile delinquent goes to live with her grandmother after her parents are arrested. Her car breaks down on the way, and she’s picked up by Bob Wolverton, the infamous I-5 killer, in a modern remake of Little Red Riding Hood.

Rating: R
Director: Matthew Bright
Starring: Reese Witherspoon, Kiefer Sutherland, Bokeem Woodbine

5. Sing (2016) 73% at Rotten Tomatoes

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Buster Moon’s dreams of owning a theater aren’t working out like he expected. It’s losing money, and he tries to save it by holding a singing competition that draws a variety of talent from all over the city.

Rating: PG
Director: Garth Jennings, Christophe Lourdelet
Starring: Reese Witherspoon, Matthew McConaughey, Seth McFarlane

4. Monsters vs Aliens (2009) 73% at Rotten Tomatoes

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Susan Murphy is hit by a meteorite on her wedding day and grows into a giant monster, terrifying her husband to be. She winds up in a secret government compound with a group of monsters and is only released to fight aliens that are determined to destroy the planet.

Rating: PG-13
Director: Rob Letterman, Conrad Vernon
Starring: Reese Witherspoon, Rainn Wilson, Stephen Colbert

3. Walk the Line (2005) 83% at Rotten Tomatoes

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Johnny Cash and his wife June Carter are one of country music’s greatest love stories. They meet on tour and form a rocky relationship that lasts until their deaths.

Rating: PG-13
Director: James Mangold
Starring: Reese Witherspoon, Joaquin Phoenix, Ginnifer Goodwin

2. Pleasantville (1998) 85% at Rotten Tomatoes

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Teenage siblings in the 1990s are transported into an idyllic 1950s sitcom world through a magic remote. Their presence begins to change the town from black-and-white to color, which sparks violence and racial divides among the townspeople.

Rating: PG-13
Director: Gary Ross
Starring: Reese Witherspoon, Tobey Maguire, Jeff Daniels

1. Legally Blonde (2001) 68% at Rotten Tomatoes

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When sorority girl and fashionista Elle Woods is dumped by her boyfriend for not being good enough, she applies (and is accepted) to Harvard law to prove she’s more than just looks.

Rating: PG-13
Director: Robert Luketic
Starring: Reese Witherspoon, Luke Wilson, Selma Blair



Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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