Matthew McConaughey Says ‘How to Lose a Guy in 10 Days’ Still Delivers His Biggest Paychecks

Matthew McConaughey says his 2003 romantic comedy “How to Lose a Guy in 10 Days” remains his most lucrative film through ongoing payments.

Speaking on the “Happy Sad Confused” podcast, McConaughey described the film as “the gift that keeps on giving” and said it generates “by far” the most “mailbox money” of any movie he has made. He recalled receiving particularly large payments each March when DVD and cable revenue were major sources of residual income, attributing the timing to Valentine’s Day.

The film, directed by Donald Petrie and co-starring Kate Hudson, follows magazine writer Andie Anderson, played by Hudson, and advertising executive Ben Barry, played by McConaughey. Both characters make separate bets involving their relationship, leading to a series of increasingly complicated romantic misadventures.

The movie helped establish McConaughey as a prominent star of 2000s romantic comedies. He later appeared in films including “Failure to Launch,” “Fool’s Gold” and “Ghosts of Girlfriends Past” before taking on more dramatic roles, including his Oscar-winning performance in 2013’s “Dallas Buyers Club.”

McConaughey has previously said that a fortune teller encouraged him to accept “How to Lose a Guy in 10 Days,” predicting that the film would be a major success. Hudson has also spoken positively about their collaboration, calling McConaughey one of her “great loves” in her acting career.