Every Matthew McConaughey Rom-Com, Ranked Worst To Best

Over the course of his decades-long career, Matthew McConaughey has tried his hand at a number of different genres, yet some of his most memorable films (though not always his best) are his romantic comedy movies. McConaughey first got his start in 1993 when he made a memorable appearance in the coming-of-age comedy, Dazed and Confused. From there, the Texas-born actor picked up projects of all different sorts, ranging from legal thrillers to sci-fi dramas. Nowadays, McConaughey has proven his dramatic acting chops via films like Interstellar and Dallas Buyer’s Club, but some lighter, more lovable films are his rom-coms.

It has been more than a decade since McConaughey last starred in a romantic comedy movie, but even then, these films have stuck firmly in popular culture. Like many other handsome leading men in the early 2000s, McCounaughey secured himself a spot as one of audiences’ beloved on-screen boyfriends, and no amount of Academy Award-nominated McConaughey movies can change that. Ultimately, these are films that aren’t necessarily of the highest quality, but still have that McConaughey charm. Plus, many of them are so nostalgic that it’s hard not to love them.

8 My Boyfriend’s Back

A Boy Returns From The Dead To Woo His Crush

Unfortunately, in order to rank McConaughey’s rom-coms, it is imperative to start with the worst. 1993’s My Boyfriend’s Back definitely fits this bill. The 1993 horror comedy follows Johnny, a senior in high school who is desperately in love with a girl named Missy. To get her attention, he stages a robbery at her job, but ends up being killed by an actual robber. However, when Johnny comes back to life as a zombie, he continues his quest for Missy’s love.

Ultimately, neither critics nor audiences were thrilled with My Boyfriend’s Back. It has a dismal 13% on Rotten Tomatoes, with many panning the film for its over-the-top silliness and sitcom-esque attitudes. Fortunately, McConaughey only played a small role in this disastrous rom-com. As his second role ever, McConaughey played Guy #2. Notably, other stars like Phillip Seymour Hoffman and Matthew J. Fox also took on background parts in the movie. My Boyfriend’s Back was a rather rocky start to McConaughey’s rom-com journey, but the good news is that he has only gone up from here.

7 Tiptoes

A Man Hides A Big Secret From His Pregnant Fiancée

Yet another awful McConaughey rom-com is his 2003 movie, Tiptoes. From the premise alone, one can see how this movie aged poorly. In Tiptoes, McConaughey plays Steven, a man who must reveal to his pregnant fiancée that his entire family are little people, in case their own child is born with dwarfism. Upon its release, Tiptoes was panned as tasteless and one of the worst movies ever made, (Yahoo.) Aside from being poorly written and edited, the movie also saw backlash for casting Gary Oldman as Steven’s twin brother due to Oldman’s lack of dwarfism and his age.

Tiptoes only fares slightly better on Rotten Tomatoes than My Boyfriend’s Back, earning a 22%. Despite the film’s poor performance, it does boast quite an impressive cast, including McConaughey, Oldman, Kate Beckinsale, and Patricia Arquette. Fortunately for all of these actors, this 2003 film has mostly been forgotten. In general, it isn’t a McConaughey rom-com that audiences should be clamoring to see. However, for those who enjoy somewhat strange and notorious films, this could be the ideal choice.

6 Fool’s Gold

A Treasure Hunter & His Ex Reunite

One more McConaughey rom-com with a somewhat bizarre premise is 2008’s Fool’s Gold. In this film, McConaughey plays Finn, a treasure hunter who has dedicated his life to finding a sunken Spanish ship. When he finds a clue to where the ship may be, he teams up with his ex-wife and her wealthy boss to find the treasure. However, Finn and Tess’s search is disrupted by Finn’s creditor, who is hoping to take the riches as his own. Despite reuniting McConaughey and Kate Hudson after their other more successful rom-com, Fool’s Gold failed to impress audiences or critics.

Without nailing its romantic comedy genre, nor its action genre,
Fool’s Gold
ends up leaving everyone disappointed.

The main critiques of Fool’s Gold, which led to the film’s 11% on Rotten Tomatoes, are the fact that the film brings nothing new or exciting to the table. The story is incredibly simple, and showcased in a bland and apathetic way. The stakes never truly present themselves, so there is little reason for audiences to care deeply about the characters. Furthermore, the movie doesn’t seem to know quite what it wants to be. Without nailing its romantic comedy genre, nor its action genre, Fool’s Gold ends up leaving everyone disappointed.

5 Ghosts Of Girlfriends Past

A Christmas Carol Retelling

Here is where McConaughey’s rom-coms begin to get a bit better. The change starts with 2009’s Ghosts of Girlfriends Past. McConaughey plays Connor, a womanizer who reunites with his childhood love at his brother’s wedding. The night before the wedding, Connor is visited by three “ghosts,” who take the forms of his previous girlfriends. By showing him his romantic past, present, and future, Connor realizes that he must put his fear aside and finally follow his heart. Alongside McConaughey, the movie stars Jennifer Garner, Michael Douglas, and Emma Stone.

Ghosts of Girlfriends Past is far from McConaughey’s best rom-com, but it is passable in comparison to some of his worse rom-coms. The movie plays out exactly as any viewer would expect from a Christmas Carol retelling, making it slightly boring, but far more familiar and comfortable than McConaughey’s odder films. With a 28% on Rotten Tomatoes and an OK box office performance, Ghosts of Girlfriends Past ranks in the middle of McConaughey’s romantic comedy line-up.

4 Failure To Launch

A Man Still Living With His Parents

Another rom-com that is a step-up for McConaughey is 2006’s Failure to Launch. In this film, McConaughey plays Tripp, a man that is still comfortably living with his parents. Concerned for him, Tripp’s parents hire an “expert” to get him out of the house: a woman named Paula who has a business of dating men like Tripp to boost their confidence. However, things become tricky when Tripp and Paula aren’t quite what the other expected, and worse, the two begin to develop true feelings for each other.

Many critics disparaged Failure to Launch for being just another formulaic rom-com, but perhaps that is what makes this movie so much better than other McConaughey rom-coms. Rather than trying to be different or unexpected, Failure to Launch gives audiences exactly what they are looking for: two attractive people who fall in love. It also helps that the movie has an incredible cast, including Sarah Jessica Parker, Zooey Deschanel, Bradley Cooper, Terry Bradshaw, and Kathy Bates. Therefore, Failure to Launch isn’t anything special, but it will give audiences exactly what they’re looking for.

3 Magic Mike

A Male Stripper Seeks Out Love

One McConaughey rom-com that some may forget about is Magic Mike. This movie follows a young man named Mike who spends his evenings headlining at an all-male strip club. Mike takes another young man under his wing at the club, but soon comes to realize that his occupation may cause trouble for his romantic life. Although McConaughey is not the titular Mike, Magic Mike still ranks as one of the actor’s best rom-coms. Magic Mike was not only a box office hit, but it also garnered a strong Rotten Tomatoes score, at 78%.

Magic Mike is able to succeed where other McConaughey rom-coms didn’t because it totally commits to its premise. Where McConaughey’s other unexpected rom-coms come across as campy or unserious, Magic Mike is dedicated to telling its story, even if it’s a bit unorthodox. On top of that, this is another movie that has a wonderfully talented cast that includes Channing Tatum, Alex Pettyfer, Matt Bomer, Joe Manganiello, and Olivia Munn. As Mike’s boss, Dallas, McConaughey is able to embody a character that is quite different from his usual role, yet he plays it with precision and accuracy.

2 The Wedding Planner

A Wedding Planner Falls In Love With Her Client

The rom-com that started McConaughey’s journey as a romantic lead was 2001’s The Wedding Planner. Based on how enjoyable this movie is, it’s no surprise that McConaughey took on other rom-com roles. In The Wedding Planner, a woman named Mary is a successful wedding planner and recently took on a massive wedding. At the same time, she has a chance encounter with a handsome pediatrician, who makes her believe in love again. However, Mary’s plans quickly hit a dead end when she discovers that her dream man is also the groom in her next wedding.

The Wedding Planner is the definition of a successful romantic comedy. This movie is not just about two people falling in love: it is messy, silly, and most importantly, heartwarming. Watching Mary unpack her own feelings on love is a delight, especially considering her job as a wedding planner. Furthermore, Jennifer Lopez’s chemistry with McConaughey is unmatched. This is a movie that takes audiences on a roller coaster of emotions, but by the end, they will be glad they went through all of it because the happy ending is just so sweet.

1 How To Lose A Guy In 10 Days

A Writer Tries To Get A Man To Leave Her In 10 Days

Finally, McConaughey’s best and most memorable romantic comedy is 2003’s How to Lose a Guy in 10 Days. The movie follows Andie, an advice columnist who is doing an experiment where she teaches her readers how to make a guy lose interest in you within 10 days. Yet, Andie’s plans backfire when she chooses Ben as her mark, a man so confident in his romance skills that he’s convinced he can make Andie fall in love with him in 10 days. What ensues is a chaotic yet touching exploration of two people finding out what they really need in love.

How to Lose a Guy in 10 Days is a classic rom-com that ranks high on many viewers’ lists of favorite rom-coms. It is funny and goofy while also hitting all the right beats to make audiences’ hearts melt. Of all his romantic opposites, McConaughey may have the best chemistry with Kate Hudson in this movie. The actors perfectly portray the mind games and unexpected feelings that develop between their characters. Ultimately, How to Lose a Guy in 10 Days isn’t the most mind-blowing movie of McConaughey’s career, but it is a romance movie that everyone should watch at least once.