Matthew McConaughey has spent more than three decades making movies.

He has starred in romantic comedies, courtroom dramas, crime films, science-fiction epics and prestige projects. He won an Academy Award for Dallas Buyers Club. He led Christopher Nolan’s Interstellar. He appeared in hits ranging from A Time to Kill to The Lincoln Lawyer.

But when it comes to the movie that still sends him the most residual money, McConaughey says the winner is not one of the titles most closely associated with the later, more serious phase of his career.

It comes from his romantic-comedy era.

And the gap is apparently not close.

During a recent appearance on Josh Horowitz’s Happy Sad Confused, McConaughey was asked about the films that continue to generate what actors sometimes call “mailbox money” — residual payments that arrive long after the original production has ended.

His answer was immediate.

The movie that still pays him more than any other is How to Lose a Guy in 10 Days.

“By far,” he said.

For anyone who remembers the early 2000s, the answer makes a certain kind of sense.

Released in 2003 and starring McConaughey opposite Kate Hudson, the romantic comedy became one of the defining movies of its era.

More than 20 years later, audiences are still watching it.

And McConaughey apparently still sees the financial evidence.

The Movie Became Bigger Than Its Original Release

How to Lose a Guy in 10 Days arrived during a period when romantic comedies were still major theatrical business.

McConaughey played Benjamin Barry, an advertising executive who makes a bet that he can make a woman fall in love with him in 10 days.

Hudson played Andie Anderson, a magazine writer secretly working on an article about how to drive a man away in exactly the same amount of time.

Neither knows what the other is doing.

That setup creates the entire movie.

Benjamin is trying to keep Andie interested.

Andie is deliberately behaving in increasingly outrageous ways to make Benjamin break up with her.

The audience knows both schemes.

The characters do not.

It became the kind of premise viewers could understand in seconds, which helped make the movie enormously rewatchable.

But according to McConaughey, the film’s financial life extended far beyond ticket sales.

McConaughey Calls It His Best “Mailbox Money”

Residuals can come from many places.

For actors whose contracts include them, payments may arrive when movies are shown on television, sold on home video, licensed to streaming platforms or reused in other formats.

The amounts can vary dramatically from project to project.

Some films generate relatively little after their theatrical run.

Others continue paying for decades because audiences keep returning to them.

McConaughey says How to Lose a Guy in 10 Days belongs firmly in the second category.

When Horowitz asked which project gives him the strongest residual payments, McConaughey identified the 2003 comedy as his biggest source of that kind of income.

Not just slightly.

“By far.”

That means a movie made during the period when McConaughey was sometimes dismissed as simply a rom-com leading man continues to outperform the rest of his filmography in at least one very tangible way.

There Was Even a Time of Year When the Checks Got Bigger

McConaughey also shared a surprisingly specific detail about when the money used to arrive.

During the era when DVD sales and cable television played a much larger role in movie economics, he noticed that some of the biggest checks connected to the film would arrive around March.

The reason was February.

More specifically, Valentine’s Day.

Year after year, audiences would return to How to Lose a Guy in 10 Days around the romantic holiday.

Cable networks programmed it.

Viewers bought or rented it.

Couples and groups of friends revisited the movie.

Then the residual impact would show up later.

For McConaughey, March became a reminder that the movie had just gone through another annual wave of Valentine’s viewing.

It is an unusually concrete example of how a movie becomes part of a seasonal tradition.

Christmas has Home Alone and It’s a Wonderful Life.

Halloween has horror franchises.

And for a certain generation of romantic-comedy fans, February has movies like How to Lose a Guy in 10 Days.

Why This One Survived

McConaughey made several romantic comedies during the 2000s.

That is part of what makes the answer interesting.

There were plenty of possibilities.

He starred with Jennifer Lopez in The Wedding Planner.

He appeared opposite Sarah Jessica Parker in Failure to Launch.

He later made Fool’s Gold with Hudson again.

Yet How to Lose a Guy in 10 Days is the title that seems to have had the strongest long-term financial life.

Part of that may be the chemistry between McConaughey and Hudson.

The movie depends almost entirely on the audience enjoying the tension between Benjamin and Andie.

Their relationship has to be ridiculous enough to generate comedy but believable enough that viewers care when the schemes finally collapse.

It worked.

The film also gave audiences a collection of scenes that became easy to remember and quote.

Andie’s deliberately terrible relationship behavior became the movie’s comic engine.

Benjamin’s increasing determination to survive the challenge gave McConaughey room to play frustration, confidence and genuine affection all at once.

By the end, the movie delivered exactly what audiences wanted from the genre.

McConaughey Still Considers It a Favorite

The financial revelation is not the only reason McConaughey continues to talk fondly about the movie.

He has also described How to Lose a Guy in 10 Days as his favorite romantic comedy from his own career.

That is notable considering his complicated history with the genre.

For a stretch of the 2000s, McConaughey became so closely associated with romantic comedies that the image began to define him.

Eventually, he stepped away from those roles and entered the career period that became known as the “McConaissance.”

Movies such as Mud, Dallas Buyers Club and Interstellar changed the way critics and audiences viewed him.

The actor who had once been treated as a reliable rom-com star became an Oscar-winning dramatic performer.

But McConaughey has never needed to pretend that the earlier movies did not matter.

And How to Lose a Guy in 10 Days may be the clearest example of why.

Audiences never stopped watching it.

The Movie’s Longevity Says Something About the Rom-Com Era

The revelation also highlights how much the movie business has changed.

In the early 2000s, a successful film could generate money through multiple long-term channels.

There was the theatrical run.

Then DVD sales.

Then rentals.

Then cable television.

Then repeat broadcasts.

Later came digital purchases and streaming.

A movie with strong rewatch value could continue generating revenue long after it left theaters.

How to Lose a Guy in 10 Days appears to have done exactly that.

Its annual Valentine’s Day popularity gave it an additional advantage.

The movie did not simply survive.

It became attached to a recurring moment on the calendar.

That kind of cultural habit can be incredibly valuable.

More Than 20 Years Later, the Checks Are Still Coming

McConaughey’s career has gone places few viewers watching him as Benjamin Barry in 2003 could have predicted.

He has won Hollywood’s highest acting honor.

He has worked with some of the industry’s most respected filmmakers.

He has appeared in movies far larger and more ambitious than the romantic comedy he made with Kate Hudson.

Yet when the question becomes which film has produced his strongest residual income, he says the same early-2000s favorite still wins.

Not Interstellar.

Not Dallas Buyers Club.

Not one of his crime dramas.

How to Lose a Guy in 10 Days.

For McConaughey, the film’s lasting popularity is not merely something he can see in fan reactions or anniversary nostalgia.

For years, he could see it in the timing of the checks arriving in his mailbox.

Especially after Valentine’s Day.

More than two decades after Benjamin Barry and Andie Anderson began playing their competing 10-day games, audiences are apparently still coming back.

And Matthew McConaughey is still getting paid for it.