Power Ranking Matthew McConaughey Date Night Movies

Matthew McConaughey was the king of romance movies in the early aughts, and let’s face it, in our minds, he still is. In 2020 Fatherly selected McConaughey as the coolest famous dad on the planet, and in 2022, we’re equally happy that his filmography changes our lives in the most meaningful way possible: by helping us to select great date night movies.

For all couples, figuring out what you can watch together is no easy task, but we’re willing to bet that most couples can agree on Matthew McConaughey. He’s got that goofy swagger dads admire, but he seems genuine in his utter over-the-top McConaughey-ness. Here are nine of his most popular date night movies, ranked from so-cheesy-it’s-good to legit classics. Saddle up! It’s the only McConaughey list you’ll ever need.

9. Fool's Gold (2008)

The conventional wisdom here is that this movie is bad and a poor McConaughey-Hudson substitute for How to Lose a Guy in 10 Days. And yet, the point of date night isn’t to watch perfect, flawless films. Plus, part of the charm of a Matthew McConaughey flick is watching him be hilarious and cool even if the movie is flawed.

Fool’s Gold is not nearly as bad as its reputation, and considering it’s a McConaughey you probably haven’t seen, give it a shot! It’s literally Hudson and McConaughey looking for treasure!

Fool’s Gold is streaming on HBO Max.

8. The Wedding Planner (2001)

Recently, Jennifer Lopez recently tried to basically remake this movie with Owen Wilson in the form of the 2022 train wreck Marry Me. This automatically makes The Wedding Planner look like Shakespeare in comparison. Can you sub Owen Wilson for McConaughey? When it comes to even rom-coms, the answer is... probably not?

The set-up of The Wedding Planner is right there in the title: Why is it that Jennifer Lopez can plan perfect weddings but can’t find love for herself? The answer? She hasn’t met McConaughey yet!

You can rent The Wedding Planner on Amazon and elsewhere.

7. Failure to Launch (2006)

It’s classic early aughts Sarah Jessica Parker! McConaughey is some guy who lives with his parents and only has friends who also live with their parents. SJP is at the top of her comedy powers here, and the fact this film came out so close to the first Sex and the City film makes you totally buy that she’s a kind of quasi-life coach who actually specializes in forcing slackers to clean up their act.

Believing that McConaughey and his co-stars have the outrageous jobs that they do is part of why we watch these movies, right?

Failure to Launch is streaming on Showtime.

6. Interstellar (2014)

Sorry, haters. This 2014 Christopher Nolan film is a banger. Starring McConaughey as a sad-dad former astronaut, this movie famously features McConaughey crying for like half an hour straight while watching a recorded video from his adult daughter. (We have no idea how long that scene actually is because it’s impossible to time it, because you too, will be crying too much.) This film co-stars Anne Hathaway, Jessica Chastain, David Gyasi, and Michael Caine. And as Michael Caine might say, this movie also featured Timothée Chalamet in a very small role as McConaughey’s son. Not a lot of people know that.

This is good for date night because of all the crying.

Interstellar is streaming on Paramount+.

5. Contact (1997)

This movie is proof that a film doesn't have to be romance-focused to be a good movie for date night. Contact also reminds you that McConaughey is a real actor and can do any genre, even dramatic, contemplative science fiction. (He sort of tried this again with Interstellar in 2014, with mixed results.) McConaughey is the quasi-love interest for an astronomer, which makes it a good option for a date night watch; people looking at the stars together — as the plot! But there's a larger story here, too; Jodie Foster is looking for aliens and McConaughey has found God. Directed by Robert Zemeckis, just a few years after he did Forrest Gump, this film is anything but predictable. Based on the novel of the same name by Carl Sagan, Contact’s basic script outline was written by Sagan and his wife, Ann Druyan.

The chemistry between McConaughey and Foster isn't smacking us in the face, but it's totally there! We’re OK to go!

You can rent Contact on Amazon and elsewhere.

4. Magic Mike (2012)

While Channing Tatum is the undisputed rom-com star of this one, Magic Mike also boasts an utterly hilarious performance from McConaughey. As a kind of male-stripper drill sergeant, McConaughey almost seems to mock his leading-man image by becoming the exact opposite of it.

Once you let go of the misplaced stigma that this movie is softcore porn, you’ll realize why everyone loved it. Yes, all these dudes look great without their shirts on (how do they get those shirts off like that?), but the charm of the movie is because it’s well-written, Tatum is awesome, and by essentially being the comic relief, McConaughey lets another guy shine for a change.

You can rent Magic Mike on Amazon or elsewhere.

3. Sing (2016)

Yes, it's an animated movie, but McConaughey is the voice of one of the main characters, a koala who needs to find creative ways to make money. Don't roll your eyes at this just because this date-night movie doesn’t have any actual romance! Sing is fantastic, will leave you feeling good, and if your little one wakes up late at night, while you’re watching it on the couch, you won’t have to turn it off.

Oh, and the songs are amazing, too.

You can rent Sing on Amazon and elsewhere.

2. How to Lose a Guy in 10 Days (2003)

This gold-standard McConaughey rom-com still holds up, big time. And part of the reason why is that it’s actually very funny. If you’ve somehow never seen this movie, you’re going to be surprised by just how great it is. It’s clever in the way all classic rom-coms are clever, but it’s so good that it feels close to a Cary Grant movie or another much older classic.

When you watch this one, it's easy to see why another movie starring McConaughey with Kate Hudson (you know, Fool's Gold, the “worst” movie on the list!) was made right away. They’re great together! Studios wanted to hit gold again with the Hudson-McConaughey combo. And you can see why. How to Lose a Guy in 10 Days is like like the Casablanca of corny rom-coms. Perfect. 10 out of 10 good!

You can rent How to Lose a Guy in 10 Days on Amazon and elsewhere.

1. Dazed and Confused (1993)

We're taking it back to 1993 for the best date night movie starring McConaughey. This comedy is timeless; even though it's a '90s movie set in the '70s, the storyline and characters are relatable for any generation. We were all introduced to Matthew as his character Wooderson, and it's easy to see why he's been in the movie-making business for so long. The movie launched his career, and while his role in the film wasn't that significant, it's how we were introduced to that catchphrase and his endless supply of charisma. It's a perfect oldie movie for date night — and deserving of the top-rated spot.

Dazed and Confused is streaming on Amazon via Freevee.

Honorable mentions: Tropic Thunder, The Beach Bum, and The Gentleman.