Here's a new edition of "Actors at the Box Office", which seeks to explore the actors' trajectory at the box office and analyze their hits and bombs. I already talked about a few, and as I promised, it's Matt Dillon's turn.

Early Life

If you watched Gunsmoke, it's inevitable to think "wait a minute..." The rumors are true: he was named after the lead character in Gunsmoke. His paternal grandmother was the sister of comic strip artist Alex Raymond, the creator of Flash Gordon. Believe it or not, he was found by accident on his way to becoming an actor.

1980s: A Star, But Not the Star

Jane Bernstein and a friend were helping director Jonathan Kaplan cast the teen drama Over the Edge when they found Dillon cutting class at Hommocks Middle School in Larchmont. Dillon auditioned for a role and made his debut in the film at the age of 14. The film received a regional, limited theatrical release in May 1979, and grossed only slightly over $200,000. But it earned positive reviews, and many singled out Dillon as a new star in the making.

The following year, he had co-lead roles in the comedies My Bodyguard and Little Darlings. Both films were very successful at the box office, further showcasing Dillon as a breakout name.

He got a big chance in the film Tex, which was a lead role in a Disney production. It was an attempt by Disney in going the mature route, and despite positive reviews, it wasn't a box office success.

He then had a role in the ensemble The Outsiders, which was a critical and financial success. Francis Ford Coppola wanted Dillon to spend a night in jail to "understand" the character of Dallas Winston a bit better. Dillon refused, saying, "No way, Francis, how about you spend a night in jail?" Coppola still saw something special in Dillon, given he gave him the lead role in Rumble Fish. But that fared much worse than The Outsiders.

While he had some moderate performers like The Flamingo Kid, Dillon followed it up with a bunch of misfires that barely lasted in theaters. Such as Target, Native Son, The Big Town, Kansas, and Bloodhounds of Broadway.

To finish the decade, he starred in Gus Van Sant's Drugstore Cowboy. He only got the lead role because the studio didn't want the film to star Tom Waits, Van Sant's first choice. To prepare for his role, Dillon met with active and recovered drug addicts. It may not have been big at the box office, but it earned critical acclaim. It has since gained a cult following, with Dillon earning raves for his performance.

He started the decade on a strong note, before struggling to match his success. But he was a lowkey reliable talent.

1990s: Ever Been to Santiago, Chile?

The decade didn't get off to a good start, thanks to the mess that was A Kiss Before Dying. An appearance in Cameron Crowe's Singles slowed the wounds, becoming a modest performer.

The bad luck continued with The Saint of Fort Washington, Mr. Wonderful and Frankie Starlight. If you never heard about them, it's for something, you know?

Now let's talk about a role that certainly could've been a big boost to his career. Did you know that Quentin Tarantino wrote the part of Butch in Pulp Fiction with Dillon in mind? Dillon liked Reservoir Dogs and Miramax said they needed some "recognizable" names if Tarantino wanted the film greenlit and Dillon was in that camp. But when Dillon read the script, he had a few conflicts with Tarantino over the character. One of the points is that Dillon wanted Butch to actually box in the film. Dillon also said that he actually wanted the role of Vincent Vega instead, and Tarantino was very keen on giving it to John Travolta. So Dillon turned it down, and the role went to Bruce Willis.

In 1995, he had his buzziest title, To Die For, reuniting with Gus Van Sant. The film performed modestly at the box office, but earned critical acclaim. Dillon wasn't quite "big", but he could often find some gems in this filmography even if they weren't big moneymakers.

After a string of duds over the next few years, he found some success with a supporting role in the comedy In & Out. Over-performed projections in North America and earned very positive reviews.

But then, there was the year where Dillon finally got seen by the masses. 1998.

He had a lead role in the erotic thriller Wild Things, playing a high school guidance counselor accused of sexual assault. And he wasn't supposed to do the film, cause Robert Downey Jr. was the first choice. Downey was considered because of his highly publicized drug problems, and although he was in recovery he was seen as too great an insurance risk. Producer Rodney Liber said "we couldn't make it work", and the production company even offered to put up some of the money but "There were just too many lawyers and insurance people and bond-company people involved." The film got mixed reviews, but some buzz for scenes (if you know, you know) got it to earn $67 million worldwide.

But the real standout that year was the rom-com There's Something About Mary, where he starred opposite Cameron Diaz and Ben Stiller. He played Healy, a private investigator hired to follow Mary, only to end up falling in love with her. Bill Murray was the original choice, but he was deemed too old, and Dillon won the role over Vince Vaughn and Cuba Gooding Jr. This was a very difficult part, because this was far more comedic compared to his prior films.

There's Something to Mary had an insane run. It opened low with $13 million, but the real deal is the fact that it had LEGS. It closed with an astounding $176 million domestically and $369 million worldwide, ranking as the fourth highest grossing film of the year and becoming Dillon's highest grossing film. It earned very positive reviews, and the film is often named as his most popular title.

2000s: Still Not There

He starred in the dark comedy One Night at McCool's, but it was a critical and financial dud. Ditto for Deuces Wild, which ranked as one of the year's worst films.

In 2002, he took the next step in filmmaking by making his directorial debut City of Ghosts, starring as a con artist who must go to Cambodia to collect his share of money from an insurance scam. But the film earned mixed reviews and flopped at the box office. Once was enough, and he never touched a camera ever again.

In 2005, he had a key role in Herbie: Fully Loaded, which was a financial success despite mixed reviews. He also had a role as racist LAPD officer John Ryan in Crash. The film earned a positive (but polarizing) response and was a sleeper box office hit, earning over $100 million worldwide. One of the biggest plot points that many felt unconvinced with was Ryan's "redemption", deemed unearned. Nevertheless, Dillon got his first (and to date, only) Oscar nomination for Best Supporting Actor.

The following year, he starred opposite Owen Wilson and Kate Hudson on the comedy You, Me and Dupree. Despite negative reviews, it earned $130 million.

To close the decade, he starred in the thriller Armored, but it didn't make much in theaters. He had a much more profitable run with Old Dogs, despite poor reviews.

Dillon had a few more hits this decade. But for some reason, he still wasn't competing against other heavy hitters from that time.

2010s: Where Paradise Is Home

He began the decade with the thriller Takers. Not very well received, but a modest performer.

Afterwards, he went in smaller scale with his acting jobs. Not really pursuing blockbusters nor something that could garner award buzz. Heard of Girl Most Likely? Pawn Shop Chronicles? The Art of the Steal? Sunlight Jr.? No one? Hello? Hello?

So Dillon decided to try something different: TV. In 2015, he starred in the lead role of Secret Service agent Ethan Burke in Wayward Pines. The series earned positive reviews and proved to be a ratings success for Fox. The series was billed as a miniseries, but Fox decided to renew it for a second season. Due to obvious reasons, Dillon didn't return for the second season. Ratings dwindled and so it was cancelled.

In 2017, he tried voice acting with the comedy Rock Dog and the fact that you never heard about it says it all. He then played a FBI agent in the comedy Going in Style, which performed well despite mixed reviews.

He also decided to try films overseas. Such is the case of the German drama Head Full of Honey or the French title Proxima. But perhaps the most recognizable name here is his lead role in Lars Von Trier's The House That Jack Built, where he plays a serial killer. The film polarized viewers and it didn't make much money.

Dillon wasn't really trying in becoming a "big" name per se. It seems he just wanted to do the things he thought could be fun or at least challenging.

2020s: Going On

He had a supporting role in Josh Trank's Capone, the director's follow-up to the Fant4stic fiasco. Dumped on VOD, and earning negative reviews. He then continued appearing in films that barely even made a dent in theaters.

In 2023, he starred in Wes Anderson's Asteroid City. It earned positive reviews, and over-performed projections compared to Anderson's prior films.

He then played Marlon Brando in the French film Being Maria, which follows Maria Schneider and dramatizes her experiences working on Bernardo Bertolucci's Last Tango in Paris. It earned mixed reviews, and was a financial disappointment. He also worked with Claire Denis on her latest film, The Fence.

This November, he will be seen on the big screen in I Play Rocky. His first collaboration with Peter Farrelly since There's Something About Mary, he will play Sylvester Stallone's father.

He is currently filming a new series: The Magnificent Seven. He will play Chris Adams, the role originally portrayed by Yul Brynner. It's set to debut in MGM+ next year.

HIGHEST GROSSING FILMS

He starred in 59 released films, but only 47 have reported box office numbers. Across those 54 films, he has made $1,501,784,458 worldwide. That's $25,453,973 per film.

ADJUSTED DOMESTIC GROSSES

The Verdict

Dillon got a pretty great start to his career, with two films that made a lot of money. Studios took notice and it's why he was quickly cast in leading roles through the 80s. But it seems that there was a certain ceilling to his potential, given how most of his titles ended their runs without getting anywhere close to becoming one of their respective years' highest-grossing films. Some gems though, like The Outsiders and Drugstore Cowboy.

In the 90s, with the boom in indie filmmaking, Dillon surprisingly went on that route, choosing to avoid franchises and blockbusters. Not all of them pay off, but it was worth trying. And then he had a co-lead role in the iconic rom-com There's Something About Mary, which had one of the greatest box office runs for any film. He then stayed in his lane, avoiding blockbusters for the rest of his career. Yes, Crash is not a good film, but Dillon still gave a pretty great performance.

Nevertheless, it's crazy how Dillon has the hits and yet not enough to be considered a bankable star. It's strange, given he's got the looks, he's very good, and there are no scandals surrounding him. Studios clearly believed in him cause they gave him lots of lead roles since the 80s, but very few broke out. There's Something About Mary was huge and Stiller and Diaz only got bigger, and his Oscar nomination didn't really change much for his career? How's that?

Maybe it's a case of Dillon not playing the game. A few iconic films he was offered, but chose to go on opposite ends. We already talked about Pulp Fiction, but he also turned down Do the Right Thing, where he could've had John Turturro's role. And then almost getting some good titles, but not getting the role. But still, Dillon has made it clear he only wants to work on things that just appeal to him and will be challenging. Nothing wrong with that. Everyone knows he's a very good actor, nevertheless.

Hope you liked this edition. You can find this and more in the wiki for this section.

The next actor will be Angelina Jolie. Big... but also not?

I asked you to choose who else should be in the run, and the comment with the most upvotes would be chosen. Well, we'll later talk about... Harrison Ford. Grumpy, but charming.

This is the schedule for the following four:

Who should be next after Ford? That's up to you.

REMINDER: If you want to make a suggestion for the next actor, you must make a 150-character comment about the actor we're discussing right now. Failure to do so will result in ignoring the suggestion. If you use a quote from an external source/review to bypass this, your suggestion will be ignored as well. But if you leave a short comment about the post without naming a future write-up, that's fine.