Though Matthew McConaughey has spent the last decade evolving as an actor into more heavyweight roles in TV series such as True Detective and critically acclaimed films like Dallas Buyers Club - for which McConaughey won his first Academy Award - the actor's name for much of the 2000s was synonymous with frothy rom-coms. McConaughey crafted a successful persona as a charismatic leading actor in Hollywood, often type-casted as the charming ladies' man, of which he played extremely well.
While the era of McConaughey-led rom-coms may be over, many of his films have become popular syndicated classics that audiences continue to enjoy over a decade later. Here's a look back on Matthew McConaughey's best romantic comedies, ranked according to Rotten Tomatoes' audience scores.
Tiptoes (2004) - 22%
Led by a surprisingly strong cast that included Peter Dinklage, Gary Oldman, Kate Beckinsale, and Patricia Arquette, Tiptoes was a bizarre art house addition to the rom-com drama. Matthew McConaughey played a small role as a man whose pregnant wife ends up falling for his dwarf brother, after worrying their baby would turn out to be a dwarf. The film never quite got over its 'oddness' despite some stellar performances and became mired in controversy after its initial premiere for firing the writer-director Matthew Bright and consequently re-cutting the entire film.
Both Bright and Dinklage have argued that the re-cut of the film ruined it, and though it was critically panned, the film developed something of a cult following in the years afterward.
EDTv (1999) - 30%
Exploring the voyeuristic nature of television audiences akin to The Truman Show, EDTv's comic satire and punchy dialogue were undeniably fun, even if it failed to offer the audience much to care about. The film followed an ordinary joe (Matthew McConaughey) who was invited to have his everyday life televised for millions to see and finds himself the center of a cultural phenomenon. McConaughey was pitch-perfect in his portrayal of Ed.
The Ron Howard-helmed film benefited under his steady hand and was bolstered by a great cast of A-listers like Woody Harrelson, Ellen DeGeneres, and Rob Reiner.
Ghosts Of Girlfriends Past (2009) - 40%
A rom-com retread of the Charles Dickens classic A Christmas Carol, Ghosts Of Girlfriends Past was a slapstick and shallow interpretation of its source material, but still enjoyable enough due to Matthew McConaughey and Jennifer Garner's endearing chemistry. McConaughey played Conner, a playboy who is reacquainted with his childhood love (Garner) on the eve of his brother's wedding, and throughout the night is visited by ghosts of ex-girlfriends who force him to confront his romantic history.
Emma Stone elevated some of the comedic moments alongside a slimy Michael Douglas, and though the film received generally unfavorable reviews, audiences found some nuggets of charm and comedy that worked.
My Boyfriend's Back (1993) - 45%
McConaughey took on a small role in Disney's back-from-the-dead comedy, which followed a nerd desperate to win over the heart of his high school sweetheart, only to wind up dead. He returns from the grave to win her over once more as a zombie. It was silly and nonsensical but likable enough insofar as audiences treated it as something of a parody, and the cast included some familiar faces in Philip Seymour Hoffman and Matthew Fox.
Despite its obvious cheesiness and offbeat jokes, My Boyfriend's Back took a valiant stab at the zombie-comedy genre and explored some interesting teen themes that audiences related with.
Fool's Gold (2008) - 48%
Co-stars Kate Hudson and Matthew McConaughey teamed up once again for this blockbuster rom-com but couldn't quite reignite the spark they found their first go-around, in large part due to a script that suffered from mild-at-best action and limp character work. For actors who brought serious chemistry in their original outing How To Lose A Guy In 10 Days, Fool's Gold was surprisingly flat. The film followed a rough-around-the-edges treasure hunter (McConaughey) and his estranged wife (Hudson) who team up one last time in search of a famed lost treasure, and in the process rekindle the lost love that existed between them.
The film was loaded with cliches, but the beachy scenery was fun and there were enough campy laughs to keep rom-com faithfuls pleased, even if high-brow critics didn't find much to like.
Failure To Launch (2006) - 52%
Cast alongside A-listers that included Zooey Deschanel, Bradley Cooper, Kathy Bates, and a fresh off Sex And The City Sarah Jessica Parker, Matthew McConaughey's Failure To Launch was a formulaic but fun film about a mama's boy who meets his match in Paula (Parker), a woman hired by his parents to finally push him out of the nest. What nobody expects is for genuine romance to blossom between them.
The film's fatal flaw was a lack of believable chemistry between McConaughey and Parker for audiences to sink their teeth into, and the star-studded cast occasionally felt wasted. Still, Deschanel stole the show comedically as Parker's unsocial roommate, and there were enough moments of sweetness and levity to keep the audience interested.
The Wedding Planner (2001) - 59%
Arguably the role that launched Matthew McConaughey's 2000s rom-com career, The Wedding Planner saw McConaughey star alongside a likable Jennifer Lopez in a film that - despite its obvious fluff and contrived plotting - still managed to be light-hearted and sweet enough to work for date-night. The film followed a wedding planner (Lopez) who lands the account for an internet tycoon's lavish wedding, only to learn that the groom is the same man she spent a romantic evening with following a near-fatal run-in with a dumpster.
A little silly and done-before, The Wedding Planner still managed to be a guilty pleasure for audiences, who agreed that McConaughey and Lopez's unlikely chemistry somehow just worked.
How To Lose A Guy In 10 Days (2003) - 77%
Still one of the most syndicated and iconic 2000s rom-coms that has stood the test of time, Matthew McConaughey and Kate Hudson turned on the charm when they starred alongside each other in this film about a magazine writer writing an article about things women do to alienate men, and a womanizer betting he can make any woman fall in love with him. The two collide with differing agendas - one to drive the other away, the other to charm them into love - and sparks fly.
Hudson was bubbly and fun, McConaughey oozed charisma, and the film - albeit silly in plotting - had all the makings of a lovable rom-com. The film was so well-liked by audiences that the new streaming service Quibi is planning to develop a modern take on it, written by The Mindy Project's Guy Branum.