Before a string of dramas, a crucial entry into the Peak TV era (True Detective) and an Oscar gave him his Serious Actor bonafide, Matthew McConaughey was Hollywood’s favorite romantic comedy leading man. From 2001 to 2009, he played swoon-worthy lotharios and reformed playboys, aka his "shirtless rom-com McConaughey" era (as he described it on Tim McGraw’s Beyond the Influence Radio). Eventually, he decided to start taking risks on more dramatic material -- a gamble we now know paid off in spades -- and the golden age of McConaughey romances came to a close.

Below, we rank the five films that helped launch the Texan charmer to superstardom, and paved the way for the "McConaissance."

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5. Ghosts of Girlfriends Past

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Image via Warner Bros.

Ghosts of Girlfriends Past is the final entry in McConaughey’s rom-com era, and unfortunately, he didn’t exactly go out with a bang. Though the film had two perfectly likable romantic leads in McConaughey and Jennifer Garner, plus a supporting cast that featured a pre-Oscar Emma Stone and a post-Oscar Michael Douglas, something didn’t quite click with this Christmas Carol retelling. The premise took the slightly sleazy persona McConaughey had been pigeonholed into past the point of charming -- there are way too many "girlfriends past." (The trailer depicts him breaking up with three different women on a conference call while reassuring his latest conquest just off screen.)

Garner feels mismatched as his childhood love, and in 2009, Stone was already evolving out of the comic relief sidekick role. Ultimately, Ghosts proved exactly why McConaughey’s instincts to move on to a new phase of his career were correct.

4. Fool’s Gold

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Image via Warner Bros.

Fool’s Gold is inarguably the lesser of his two rom-com collaborations with Kate Hudson. The chemistry is there, but the plot contrivances -- a given in any rom-com, to varying success -- are a bit harder to look past. The duo play a pair of divorced treasure hunters in a race to find a legendary cache before their rivals. A pre-fame Kevin Hart plays Bigg Bunny, an unfortunately stereotypical gangster rapper whose propensity for violence feels at odds with the breezy slapstick comedy on display.

Despite McConaughey being in his beachy boho element, at this point, it was becoming clear that he was phoning it in. There are some flashy set pieces (scuba dive searches, boat chases, and a climactic plane takeoff), but the film lacked spark, and was panned critically upon release.

3. Failure to Launch

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Image via Paramount Pictures

The mismatched romantic leads in Failure to Launch works ever so slightly better than in Ghosts, because here, at least it’s on purpose. Sarah Jessica Parker is a put-together professional "life coach" pitted against McConaughey’s overgrown man child. Paula’s (Parker) business of romancing adult men out of their parents’ homes may be a bit harebrained, but it’s not the silliest meet-cute in rom-com history.

Instead, where the film falls apart is the absurd amount of physical comedy (there’s a truly odd amount of comic animal attacks in this movie, featuring a dolphin, chipmunk, lizard, and a mockingbird). The lackluster follow-through is also an issue, as Tripp’s family resolves to tie him up and force his reconciliation with Paula, a plot device of which most fanfiction writers would steer clear. The script wasn’t doing anyone any favors, but there are at least a solid set of sidekicks in Zoey Deschanel, Justin Bartha, and Bradley Cooper (the latter in their pre-Hangover days).

2. The Wedding Planner

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Image via Sony Pictures

The first entry in McConaughey’s rom-com run saw him riding the wave of Jennifer Lopez’s career peak (with its release in 2001, she became the first woman to have a number one film and album in the same week). It’s really J.Lo’s show as the inexplicably Italian wedding planner Mary Fiore, but sensitive pediatrician Steve Edison is one of McConaughey’s best leading men.

This isn’t the overconfident charmer McConaughey would later be typecast as: he works with kids! He wears glasses! He’s rarely ever shirtless! And most importantly, he’s conflicted about falling for Mary while planning a wedding with his fiancée. The duo can’t fight their attraction to each other, despite the off-limits nature of their relationship. And of course, the audience can’t help but root for them, either. Plus, it’s part of the Judy Greer rom-com BFF canon, which makes it all the better.

1. How to Lose a Guy in 10 Days

Matthew McConaughey and Kate Hudson in How to Lose a Guy in 10 Days
Image via Paramount Pictures

When you think of a Matthew McConaughey rom-com, it’s probably How to Lose a Guy in 10 Days that comes to mind. A staple of the early aughts, the mutual game playing between McConaughey’s Ben and Hudson’s Andie is just the right amount of screwball to make the premise work. The chemistry between them is so undeniable that the romance works even when Andie is actively trying to drive Ben away.

This movie has everything a rom-com lover could want… a moment on the kiss cam at the Big Game; a grounding trip home to visit the family that makes the couple fall even harder; a performance of "You’re So Vain" -- McConaughey style -- in front of a crowd at a fancy party. Bonus points for Hudson’s iconic yellow dress and an all-time great rom-com BFF in Kathryn Hahn, but the climactic declaration of love out on the bridge based on a game of "Bulls**t" takes the cake.

KEEP READING: Why ‘The Lincoln Lawyer’ Was the Start of the McConaissance