Overnight Delivery
Readers, we truly had no idea that this rom-com existed until we made this ranking. In their first film together, Reese Witherspoon and Paul Rudd play a stripper and a college student, respectively, who go on a road trip to stop Rudd's girlfriend from receiving a vicious breakup letter he sent by express mail. No, we did not make that up. Yes, this is a real movie that came out in 1996.
Legally Blonde 2: Red, White & Blonde
We are just going to bend and snap and move right on with our list rather than spend too much time on this disappointing 2003 sequel. Court adjourned!
How Do You Know
Almost 15 years after their first rom-com romp, Witherspoon and Rudd teamed up again for this 2010 movie (and they invited Owen Wilson in to play the third point in their love triangle). But their second attempt doesn't fare much better, unfortunately, proving that sometimes two rights can make a wrong.
This Means War
Tom Hardy and Chris Pine playing CIA agents/BFFs battling it out for Witherspoon's affection? The 2012 rom-com with a spy-twist threatened us with that very good time, but, in a truly bizarre twist, the combined charm of the three leads to just a "meh" offering.
The Importance of Being Earnest
The 2002 adaptation of Oscar Wilde's classic play is easy, breezy and kind of forgettable. Hey, that's the importance of being honest.
Home Again
Written and directed by Hallie Meyers-Shyer, the daughter of rom-com queen Nancy Meyers, this lighthearted 2017 outing is one we like more than most people. (And it has the Rotten Tomatoes rating to prove it.) Sure, it could have been the classic Meyers house porn, but it was delightful watching Witherspoon, playing a recently separated single mother, banter with a trio of handsome young filmmakers. Sometimes, that's all we need.
Your Place or Mine
Witherspoon partnering with Ashton Kutcher, a fellow genre vet thanks to No Strings Attached, A Lot Like Love and What Happens in Vegas, seemed like a most satisfying way to scratch our rom-com itch. Alas, this Netflix movie left us feeling a little hollow, especially after the duo's supposed-to-be-grand reunion after spending most of the film apart felt as stiff as Kutcher and Witherspoon's awkward demeanor during their press tour.
Just Like Heaven
Pair Witherspoon with equally as beloved celebrity Mark Ruffalo and it's basically a crime to not love the finished product. Yes, the plot is a little eyebrow-raising and could easily be read as the set-up for a horror flick—he plays a widowed architect who discovers his new apartment is haunted by a comatose woman—but when you have the chemistry and charm of these two actors, it's a match made in heaven.
Four Christmases
Technically, this is a Christmas movie, but it is also a rom-com about a couple attempting to visit their four divorced parents' home for the holidays. While the 2008 movie is fun enough, there aren't exactly sparks between Witherspoon and Vince Vaughn.
Legally Blonde
Happy people don't kill their husbands, and rom-com lovers don't ever pass on the opportunity to watch this 2001 gem, which finds Witherspoon at as aspiring attorney Elle Woods, arguably her most lovable role. Legally Blonde is cinematic comfort food, always hitting the spot, even twenty years later. Jennifer Coolidge, Luke Wilson (who also pops up as the laidback love interest in Charlie's Angels and The Family Stone around this era), Selma Blair, Linda Cardellini and Victor Garber all deliver iconic supporting performances, but this is Witherspoon's movie, through and through. And, whoever says otherwise, is seriously disturbed!
Sweet Home Alabama
Okay, okay, wait! Before you come for us for not ranking Legally Blonde as Witherspoon's best rom-com, hear us out: The love story is simply more important in Sweet Home Alabama! Add in two viable and ridiculously goodlooking love interests (played by Josh Lucas and Patrick Dempsey), an iconic supporting turn from a Jaclyn Smith-wearing Melanie Lynksey and a role that really captures Witherspoon's Southern sass and we can't resist the charm of rom-com.