Ranking the Romantic Comedies of Reese Witherspoon

      Casey Chong ranks the romantic comedies featuring Reese Witherspoon…

      Similar to Julia Roberts and Meg Ryan, Reese Witherspoon is a prominent name in the rom-com genre, though she has also branched out into biographical dramas (like Walk the Line and Wild) and thrillers (such as Freeway and Fear). Nevertheless, it was the romantic comedy genre that propelled Witherspoon’s career, and with her return to this familiar territory in Prime Video’s You’re Cordially Invited, it’s an opportune moment to reflect on her romantic comedies, ranked from least to most impressive.

      How Do You Know (2010)

      How could a romantic comedy like this cost an astonishing $120 million to produce? Four factors contribute: the high salaries of its stars - with Reese Witherspoon, Jack Nicholson, and Owen Wilson each earning over $10 million - plus the substantial paycheck for director James L. Brooks, along with the time he spent during production and significant reshoots. However, How Do You Know fails to justify its enormous budget. The film surprisingly lacks essential stakes or conflicts, even with its potentially intriguing love triangle involving Reese Witherspoon, Owen Wilson, and Paul Rudd's characters. Its erratic pacing, combined with weak chemistry – both between Witherspoon and Wilson and Rudd – along with Brooks’ usual star Jack Nicholson (in his unfortunately final performance), ultimately cannot rescue this tepid and overly long romantic comedy.

      This Means War (2012)

      What could have been a clever action-comedy infused with rom-com elements, akin to True Lies and Mr. & Mrs. Smith, got derailed under McG’s direction. This Means War boasts a fantastic cast, including Chris Pine, Tom Hardy, and Reese Witherspoon, where both men play CIA agents vying for the affection of the same woman. Unfortunately, the ensuing “war” doesn't deliver the entertaining love triangle one would hope for, as McG’s tone-deaf direction fails to land any genuine humor. The performances come off as childish, with McG seemingly confusing silly antics for authentic screwball comedy. Even the typically energetic Witherspoon, a mainstay of the rom-com scene, can’t lift this misguided project from mediocrity. The film struggles to generate laughs, often falling short, while the action sequences feel rushed and frenetic, comprising numerous close-ups and rapid editing.

      Overnight Delivery (1998)

      This lesser-known rom-com, originally released for the direct-to-video market, features a pre-fame Reese Witherspoon (without her iconic blonde hair) alongside Paul Rudd in their first collaboration. Witherspoon plays a stripper and Rudd a neurotic college student on a time-sensitive mission to retrieve a package before the delivery person, played by Larry Drake, reaches Rudd's girlfriend at the University of Memphis. It’s a loud, zany comedy where Rudd’s over-the-top performance resembles someone on a sugar high. However, if you can overlook his frantic acting, he shares decent chemistry with the sassy Witherspoon. The brisk pacing, driven by Jason Bloom, who previously directed Pauly Shore in Bio-Dome, keeps the film lively, blending screwball comedy, romantic comedy, and road-movie elements, including a wacky highway chase where Rudd’s character attempts to reclaim the package from a moving delivery truck.

      Home Again (2017)

      Hallie Meyers-Shyer, daughter of renowned rom-com filmmaker Nancy Meyers, made her directorial debut with Home Again, which navigates the age-gap romance between an older woman (Reese Witherspoon) and a younger man played by Pico Alexander. Witherspoon shines alongside her co-stars – Alexander, Nat Wolff, and Jon Rudnitsky – who portray a trio of aspiring filmmakers in solid supporting roles. One storyline involves Witherspoon’s single-mother character permitting the three filmmakers to move into her home after a single bar encounter, which may seem improbable. However, this premise can be forgiven if Shyer fully embraces the absurdity and injects enough fun and personality into it. Unfortunately, her pedestrian direction often undermines the movie’s charming cast.

      Four Christmases (2008)

      The pairing of delightful Reese Witherspoon and cynical Vince Vaughn is what makes Four Christmases an enjoyable holiday rom-com. Their winning chemistry enchants audiences, while the plot, involving a couple forced to abandon their Fiji vacation due to bad weather and subsequently visiting four of their divorced parents, explores the challenges of dysfunctional family dynamics through a mix of absurdity and awkwardness. Directed by Seth Gordon in his debut, who later directed Horrible Bosses, the film sometimes falters with its hit-or-miss broad humor. Nevertheless, his energetic direction, combined with an equally lively cast, helps elevate the film above its shortcomings.

      Your Place or Mine (2023)

      Aline Brosh McKenna, familiar with rom-coms thanks