Matthew McConaughey has identified the 2003 romantic comedy "How to Lose a Guy in 10 Days" as his highest-earning film to date in terms of residual payments. He described the movie, in which he starred alongside Kate Hudson, as "the gift that keeps on giving."
In an episode of the "Happy Sad Confused" podcast, McConaughey stated that the film provides "by far" the most "mailbox money" of any project he has worked on. He recalled that in previous years, when DVDs and cable television were the primary revenue streams, he would receive significant checks each March, likely due to Valentine's Day viewership. McConaughey also expressed his affection for the film, calling it "probably my favorite rom-com I’ve done, and a lot of people love that rom-com."
He views the movie as a significant anchor in the rom-com genre. Directed by Donald Petrie, "How to Lose a Guy in 10 Days" features McConaughey as advertising executive Ben Barry, who makes a bet he can make a women's magazine columnist, Andie Anderson played by Hudson, fall in love with him in 10 days. Simultaneously, Anderson is on a mission for an article to drive a new boyfriend away within the same timeframe.
The film solidified McConaughey's status as a prominent actor in 2000s romantic comedies, following his role in "The Wedding Planner" in 2001. His subsequent rom-coms included "Failure to Launch," "Ghosts of Girlfriends Past," and "Fool's Gold," which reunited him with Hudson. Later in his career, McConaughey shifted to more dramatic roles, earning an Academy Award for his performance in the 2013 film "Dallas Buyers Club."
McConaughey has previously shared an anecdote about how a fortune teller influenced his decision to take the role in "How to Lose a Guy in 10 Days." He recounted that the individual approached him and urged him to accept the part, predicting it would be an enjoyable and financially successful experience. Although initially skeptical, McConaughey found the advice compelling and accepted the offer the following day.
Kate Hudson has also spoken positively about her experience working with McConaughey on the film, describing him as one of her "great loves in work" and feeling fortunate to have shared the experience with such a talented and enjoyable co-star.