Matthew McConaughey’s 2003 Rom-Com Still Out-Earns His Entire Film Career

More than two decades after ‘How to Lose a Guy in 10 Days’ hit theaters, Matthew McConaughey is still cashing checks from the romantic comedy bigger ones than he gets from any other film he’s made.

The actor opened up about the film’s surprisingly durable paycheck during an appearance on Josh Horowitz’s ‘Happy Sad Confused’ podcast, revealing that the 2003 flick generates what he calls his best “mailbox money” by a considerable margin.

McConaughey didn’t mince words when describing the film’s financial staying power. He called it “the gift that keeps on giving” and said it’s probably his favorite romantic comedy that he’s starred in.

“By far. By lengths,” McConaughey said when comparing its earnings to his other projects.

The durability of the paycheck speaks to how the film has remained a staple across airlines, television networks, and streaming services McConaughey even joked about its enduring popularity in sorority houses across the country.

The 2003 film paired McConaughey with Kate Hudson in a premise built on competing schemes. McConaughey’s character, advertising executive Benjamin Barry, bets he can make a woman fall in love with him. Hudson’s magazine writer Andie Anderson is secretly planning an article on how women can sabotage relationships. Chaos and genuine feelings ensue.

Director Donald Petrie turned the concept into a box office winner. Made for $50 million, it pulled in roughly $177.5 million worldwide and has apparently never stopped working.

McConaughey recalled that during the DVD and cable era, he’d see particularly sizable payments arrive each March, right after the Valentine’s Day viewing season wrapped up.

The film helped launch McConaughey into rom-com stardom during the 2000s. He’d go on to make ‘The Wedding Planner’, ‘Failure to Launch’, and ‘Ghosts of Girlfriends Past’, but none have matched ‘How to Lose a Guy’ in the residual income department.

Much of the credit goes to the undeniable chemistry between McConaughey and Hudson. Their performances transformed a deliberately absurd premise into one of the early 2000s’ most beloved romantic comedies. Hudson has even hinted she’d be open to revisiting the characters for a sequel if the timing and script were right.

Twenty-plus years later, ‘How to Lose a Guy in 10 Days’ remains more than just a beloved film in McConaughey’s filmography. It’s his most reliable money maker and apparently, shows no signs of stopping.