Guess which Matthew McConaughey movie paid him the most? Not the one you think.
Matthew McConaughey says his biggest cheque isn’t the one you’d guess — and the film behind it is still paying him years after release.
Here’s one for the trivia fans: Matthew McConaughey may be the bloke behind those Oscar-winning turns and McConaissance dramas, but it’s not dramatic films or gritty mini-series that bring in his thickest stack of royalty cheques. The role that keeps his accountant happy? Good old Benjamin Barry from How to Lose a Guy in 10 Days. Yes, really. Not Interstellar. Not True Detective. That fizzy 2003 romcom opposite Kate Hudson is apparently his ongoing cash cow.
During a recent chat on the Happy Sad Confused podcast, McConaughey summed it up himself: 'How to Lose a Guy in 10 Days is the gift that keeps on giving. I think it’s probably my favourite romcom I’ve done. And a lot of people love that romcom. And it still pays the best mailbox money film I’ve ever done.'
For those not fluent in Hollywood lingo, 'mailbox money' is code for passive royalty earnings—the sort that show up without having to lift a finger. So as far as lucrative gigs go, trying to win and lose Kate Hudson at the same time beats all his other films, at least in terms of easy earnings.
Quick plot refresher in case you managed to dodge this one: McConaughey plays Benjamin Barry, an ad exec who bets he can make any woman fall for him in ten days. Enter Andie Anderson (Kate Hudson), who’s got her own magazine assignment—drive a bloke away in under a fortnight, using every anti-dating cliché in the book. Obviously, hijinks and inevitable genuine feelings ensue. Anyone with the right streaming login can watch it now on Prime Video, Paramount+, or Apple TV.
'How to Lose a Guy in 10 Days' keeps paying out the best residuals of McConaughey’s career.
Beyond the Romcom Phase
Not to say the man hasn’t had options since. If you think his best-earning film might be a one-off, here’s a quick rundown of his career since then. After playing the long-suffering romantic lead (again) in The Wedding Planner (2001), Failure to Launch (2006), Fool’s Gold (2008), and Ghosts of Girlfriends Past (2009), McConaughey took a very deliberate left turn away from lovelorn beach hunks.
Enter the McConaissance: He flew a spaceship in Interstellar for Christopher Nolan, brooded over existential crimes in True Detective (series one, still the only one that actually matters), and picked up a run of character roles that proved he could do a lot more than charm someone by the pool.
What’s Next?
His next big job is right around the corner: McConaughey will star in a new comedy series, Brothers, which lands on Apple TV+ on 23 September 2026. So that’s his mailbox sorted for a few more years, presumably. In the meantime, though, it turns out being in the right romcom at the right time pays more than saving the planet or solving murders on TV.