Casey Chong ranks the romantic comedies of Reese Witherspoon…
Much like Julia Roberts and Meg Ryan, Reese Witherspoon is synonymous with the rom-com genre, even though the actress has explored different genres such as biographical dramas (Walk the Line, Wild) and thrillers (Freeway, Fear). And yet, it was the rom-com genre that skyrocketed Witherspoon’s career, and as she returns to her familiar comfort zone in Prime Video’s You’re Cordially Invited, it’s time to look back at her romantic comedies, ranked from worst to best.
How Do You Know (2010)
How did this romantic comedy cost a whopping $120 million to make? Four reasons: the actors’ high salaries with Reese Witherspoon, Jack Nicholson and Owen Wilson alone costing north of $10 million each, along with director James L. Brooks’ equally high paycheck along with the time he spent in production and ultimately, hefty reshoots. However, How Do You Know hardly justifies its inflated cost. The movie surprisingly lacks much-needed stakes or conflicts, despite the story’s potentially interesting love triangle angle between Reese Witherspoon, Owen Wilson and Paul Rudd’s characters. Erratic pacing, coupled with the lackluster chemistry – neither Witherspoon with Wilson nor Rudd – and not even Brooks’ regular Jack Nicholson (in his unfortunately final acting performance to date) can do much to save this tepid and overlong romantic comedy.
This Means War (2012)
In what could have been a fun high-concept action comedy with rom-com tropes in the vein of True Lies and Mr. & Mrs. Smith, all it took was McG to run the movie into the ground. This Means War even features a trio of stellar cast including Chris Pine, Tom Hardy and Reese Witherspoon, with both guys working as CIA agents falling in love with the same girl. The titular war ensues and instead of an entertaining battle of the love triangle, McG’s tone-deaf direction seems to be clueless about how to hit the right punchline. Their acting is painfully juvenile with McG seemingly mistaking annoyingly childish gags for a genuine screwball-comedy vibe. Not even the typically perky Witherspoon, who is a stalwart of the rom-com genre, can help elevate this misguided mess above mediocrity. The movie tries hard to be funny, only to fall flat more than often while the action is hastily put together with lots of close-ups and rapid-fire editing.
Overnight Delivery (1998)
This lesser-known rom-com, which was released for the direct-to-video market, features a pre-fame Reese Witherspoon (and minus her signature blonde hairstyle) and Paul Rudd teaming up for the first time. One’s a stripper and the other is a neurotic college student, who are on a race-against-time mission to retrieve the titular package before the delivery guy played by Larry Drake reaches Rudd’s girlfriend at the University of Memphis. It’s a zany, loud comedy where Rudd tends to overact like he’s on a sugar rush downing too much Coke. If you can get past his frantic performance, he does share a decent chemistry with the sassy Witherspoon. The pace is brisk with Jason Bloom, who previously directed Pauly Shore in Bio-Dome, propels his movie with a lively mix of screwball comedy, rom-com, road-movie genre and at one point, a wacky highway chase scene that sees Rudd’s character try to recover the package inside the moving delivery truck.
Home Again (2017)
Hallie Meyers-Shyer, the daughter of the rom-com filmmaking queen Nancy Meyers, made her directorial debut with Home Again, which explores the age-gap romance of an older woman (Reese Witherspoon) falling for a younger guy played by Pico Alexander. Witherspoon is charming while her co-stars – Alexander, Nat Wolff and Jon Rudnitsky – who play the trio of aspiring filmmakers deliver decent supporting turns. One of the main stories revolving around Witherspoon’s single-mom character allowing the three young filmmakers to move into her home that she only met them one time in a bar may sound far-fetched. But such a premise is forgivable if Shyer embraces the implausible story wholeheartedly with enough fun and personality. Too bad her pedestrian direction often undermines the movie’s otherwise delightful cast.
Four Christmases (2008)
The on-screen pairing of the delightful Reese Witherspoon and the cynical Vince Vaughn is what makes Four Christmases a fun, holiday rom-com. Their winning chemistry works like a charm while the story itself, which revolves around the liberal-minded couple forced to cancel their Fiji vacation plan due to bad weather and ends up spending the whole day visiting four of their divorced parents, gamely explore the dysfunctional families filled with a mix of absurd and awkward situations. Pre-Horrible Bosses’ Seth Gordon, who made his directorial debut here, tends to overwhelm with a series of hit-and-miss broad humor. But his lively direction, coupled with the equally energetic cast manages to overcome its flaws from turning the movie into a lump of coal.
Your Place or Mine (2023)
Aline Brosh McKenna, who is no stranger to writing rom-coms from Three to Tango to The Devil Wears Prada and Morning Glory, made her directorial debut in Your Place or Mine, a cliched-ridden rom-com that is partly When Harry Met Sally, minus the iconic “orgasm” scene. Your Place or Mine benefits from Reese Witherspoon and Ashton Kutcher’s respectively charming performances as two best friends who swap homes, where the former is participating in an accounting program in New York City while the other helps take care of her son, Jack (Wesley Kimmel) in her L.A. home. The movie may have been predictable, but it doesn’t take rocket science to figure out how the story is going to end. But McKenna’s genre know-how direction approaches the movie like comfort food that you are familiar with, thanks to the two principal actors’ chemistry and a few worthwhile moments, namely Kutcher’s character subsequently manages to spend quality time with Kimmel’s Jack.
Sweet Home Alabama (2002)
Sweet Home Alabama may have been patchy in places but other than that, this is one of Reese Witherspoon’s best rom-coms, complete with the effervescent actress embracing her Southern drawl. She’s endlessly charismatic here and shares great chemistry with Patrick Dempsey and Josh Lucas. The latter is where the movie earns a plus point with Andy Tennant’s assured direction exploring the love-hate relationship between Witherspoon and Lucas. It also helps the movie get an extra boost from Candice Bergen’s solid supporting role as the sceptical mayor who’s having trouble accepting her son (Dempsey) engaging to marry Witherspoon’s character.
Just Like Heaven (2005)
You got to give it to Mark Waters for mixing and matching two different genres – rom-com and supernatural fantasy – and turn Just Like Heaven into a whimsical and entertaining comedy. Pairing Reese Witherspoon, who plays the wandering spirit after her body is in a comatose state following a car accident with Mark Ruffalo’s widowed architect is well, a match made in heaven. Their love-hate chemistry immediately clicks from the moment they meet under the unusual circumstances, especially given the nature of Witherspoon’s character. Their hilarious banter, coupled with Waters having a field day poking fun at the supernatural genre (the scene where Ruffalo’s character hires everyone he can think of to help exorcise her away from occupying his home comes to mind).
Legally Blonde (2001)
Legally Blonde is where Reese Witherspoon finally catapulted to Hollywood stardom. It’s a movie that defines her career and above all, her knack for playing perky characters in the rom-com genre. What distinguishes this iconic 2001 hit comedy is Robert Luketic’s confident direction of turning Amanda Brown’s titular comic novel into a sunny, yet relatable coming-of-age angle of how Witherspoon’s Elle Woods overcoming the dumb-blonde stereotype by proving herself and particularly, her unappreciative boyfriend (Matthew Davis) that she can achieve the impossible. And that is, scoring the necessary grade to enter Harvard Law School. Her sheer determination in the name of love and ultimately, self-discovery helps elevate the storytelling while Witherspoon’s undeniable charisma and optimistic personality is one for the ages.
How would you rank Reese Witherspoon’s romantic comedies? Let us know on our social channels @FlickeringMyth…
Casey Chong
Originally published February 1, 2025. Updated June 21, 2025.
