Why Didn’t Matt Dillon Become A Movie Star?

Why Didn’t Matt Dillon Become A Movie Star?

Why Didn’t Matt Dillon Become A Movie Star? By Simon Thompson.

Some dead Roman guy named Seneca once said that “luck is what happens when preparation meets opportunity”. Now I’m not for one second trying to rain on the parade of an esteemed Ancient Roman philosopher here  but clearly Seneca didn’t study the career of Matt Dillon, a guy who had all the requisite looks, talent, and acting ability to be a major movie star but for some reason his career never took off to the extent that it should have, especially when you consider that Roger Ebert himself referred to Dillon as ‘the best actor in his age-group’ ( which is an incredible compliment given that Dillon’s age group includes Tom Cruise, Brad Pitt, Johnny Depp, Sean Penn, Nicolas Cage, and Robert Downey Jr).

Matt Dillon was born in 1964 in New Rochelle, New York to Mary Ellen and Paul Dillon, a homemaker and sales manager respectively. Artistic talent was something that clearly ran in the Dillon family with Paul Dillon being a keen portrait painter and his great uncle Alex Raymond being the original creator of the comic strip Flash Gordon. Despite his clear artistic lineage acting was something that Matt Dillon fell into by complete accident. One day when he was cutting class filmmaker Jonathon Kaplan happened to be scouting Dillon’s high school for potential actors to star in his upcoming movie Over the Edge and spotting his potential instantly Kaplan had him audition for a part. Dillion of course passed the audition process and was subsequently given his cinematic debut in the role of Ritchie White.



Over The Edge (1979) was a daring no-holds barred look at frustrated teenage suburban life, following a group of kids completely neglected by their parents who decide to rebel against both the tedium of their surroundings and their uninterested parents by vandalism, under-age drinking, doing drugs and fighting with the local cops. Although Ritchie White isn’t the main protagonist Matt Dillon absolutely steals the movie, giving a performance displaying both confidence but also an authentic doomed sense of vulnerability so that when I was watching the movie, I still couldn’t quite believe that he was 15 when he starred in it. 

Because of bad publicity concerning movies which featured gang or youth violence such as The Warriors, Over The Edge was given a limited theatrical release. However, a 1981 run at Joseph Papp’s Public Theatre in New York as part of a program to promote overlooked movies (which led to critics such as Vincent Canby of The New York Times giving it a glowing review) and it being constantly played on HBO in the mid- late 1980s both helped to foster the movie’s reputation as a cult classic. 

Despite lukewarm box office returns upon its release Over the Edge is the pinpoint moment when Matt Dillon began to garner a reputation for being one of the most exciting young talents in American acting. As the 1970s became the 1980s, Matt Dillon established himself as a much sought after straight down the middle teen heartthrob, with roles in movies such as sex-comedy Little Darlings (1980), high-school drama My Bodyguard (1980), the romantic drama Liar’s Moon (1982), and the first of three straight SE Hinton novel adaptations with Tex (1982). These roles were given to Dillon because he could not only act, but unlike the litany of 27 year olds playing teenagers in high-school dramas he was actually in the same age-range as the characters that the was playing. 

1983, would be a huge turning point in Dillon’s career. At 19 years old he was looking for more challenging work and struck paydirt through a two film collaboration with legendary director Francis Ford Coppola.  Coppola by this point was being treated as if he had pissed in everyone’s cereal by Hollywood’s producers and moneymen because of the failure of his movie One from the Heart (1982) so he was in desperate need of a project to put himself back into the spotlight.  Thanks to a school librarian in California named Jo Ellen Misakian sending Coppola a 15 page petition of kid’s signatures asking him to direct their favourite book The Outsiders by SE Hinton, Coppola took it upon himself to read the novel, subsequently discovered how much he enjoyed it ( he would go onto to the say relationship between the kids in the novel reminded him of being a summer camp counsellor)  and immediately went out to acquire the film rights to another one of SE Hinton’s novels titled Rumble Fish so he could film movies of the two back to back. 

Coppola intelligently realised that for The Outsiders (1983)he wanted an ensemble cast of Hollywood’s outstanding young talent to headline the movie, casting Matt Dillon to play the character of Dallas. Looking back 40 years later The Outsiders is the American cinematic equivalent of Barcelona’s La Masia academy, with Matt Dillon being on the same bill with the likes of Patrick Swayze, Tom Cruise, Diane Lane, Emilio Estevez, and Rob Lowe. Despite the star-studded cast Dillon absolutely shone in The Outsiders,proving to a wider audience who hadn’t seen Over the Edge that he wasn’t some cutesy teen-idol pretty boy, but a serious actor giving his performance as Dallas Winston a mixture of James Dean-like brooding with a Cagney style sense of febrile menace. 

The Outsiders would go on to make $33 million off a $10 million budget, received positive reviews from critics, made Coppola a bankable name again, as well as making stars out of the likes of Cruise, Swayze, and Lowe. For Dillon The Outsiders showed a wide audience his ‘edge’, for a lack of a better term, as an actor. If his debut Over The Edge is what made him a star then this movie is the one that showed directors his potential to have a career beyond his teens. 

Rumble Fish, Matt Dillon’s second Coppola collaboration would take his career to another level of indie cool. Releasedthe same year as The Outsiders, Rumble Fish is like The Outsiders’ more interesting cousin. In typical Coppola fashion after getting his foot back into the Hollywood door with a success he went out and made a bold, black & white avant-  garde teen drama. Taking inspiration from German expressionism, film noir, the French New Wave, and Godfrey Reggio’s time-lapse photography piece Koyaanisqatsi, Rumble Fish was a truly daring and original follow up to The Outsiders.

Dillon plays Rusty James, a teenage gang member in small town Oklahoma, who wants to be as feared and respected as his older brother the Motorcycle Boy a colour -blind, partially deaf, mysterious chain smoker Camus-esque existentialist philosopher played by Mickey Rourke. Dillon is absolutely fantastic in Rumble Fish. Even though Rourke’s character is the emotional centre of the movie to an extent and because it’s prime Mickey Rourke he nearly steals the show with his performance Dillon still manages to hold his own with such a charismatic and powerful actor in the scenes where the two of them are together, whilst also proving that he had the essential star-quality to carry the movie as the lead. 

For Dillon Rumble Fish represented a newly found sweet spot between being a household name and a cult actor at the same time. Although the movie wasn’t financially a success in America (probably due to audiences not understanding its art-house aesthetics and existentialist themes) it has gone on to develop a cult-following of those that now love it for the very same reasons it struggled to make money in the first place. Whether he knew it or not Matt Dillon was now the coolest actor on planet earth, but herein lies an issue which has plagued Dillon his entire career that- of not being savvy enough when it comes to picking projects. 

Let me take two examples of actors in Dillon’s age range whose careers started later on, Johnny Depp and Brad Pitt. Although both were a lot older than Dillon when they started both of them made concentrated efforts to fight the teen-idol hunk of the month pigeon-hole category that Hollywood tried to force them into through making movies with interesting directors and scripts. Instead of starring in a Se7en or an Ed Wood type movie the first thing Dillon went and did after Rumble Fish was a by the numbers Garry Marshall comedy named The Flamingo Kid (1984).

 The 1985-1988 period of Matt Dillon’s career is what I would describe as his pick and mix era. Whilst I don’t think Dillon was cynically trying to become a movie star, his choices from around this timeframe have a strange almost dissonant quality to them as he tried to make the perilous transition from teen-star to serious adult actor. Action-thriller Target (1985) saw Matt Dillon paired with one of the greatest American actors of all time in Gene Hackman and one of the greatest directors of all time in Arthur Penn, but sadly received a so-so response critically and commercially. Dillon followed that up with Rebel (1985)an Australian World War II period musical (based on the play No Names, No Packdrill by Bob Herbert) that faded into nothing at the Australian box office, only making A$886,769 off a A$5,000,000 budget. 

Dillon would then choose to take on a prestige piece with an adaptation of Richard Wright’s seminal novel Native Son (1940). The movie adaptation however was released to a tepid reception at the box office and by critics such as Vincent Canby of The New York Times who accused it of softening the themes and ideas of Wright’s original novel. The crime genre would be where Dillon would find himself next, with the young actor making two crime movies back to back in 1987 and 1988. The first, The Big Town (1987) was a dark neo-noir where Dillon portrayed a professional gambler from a small town moving to the big city. Despite the movie boasting the likes of Tommy Lee Jones, Diane Lane, and Bruce Dern in its cast the film failed to resonate with audiences and received mixed-reviews from critics, which is a shame because it’s a terrific piece of 1950s-set neo-noir. 

Kansas (1988) would see Dillon teamed with brat pack alum Andrew McCarthy. This movie was given a brutal curb stomping both by critics such as Siskel and Ebert who criticised its cliched plot calling it ‘recycled from Horatio Alger novels’ and by residents of the Kansas area who said the movie made them look like ‘bumpkins straight out of Little House in The Prairie’. It was becoming clear that Dillon’s career needed a lifeline, and he would find that in the shape of an ambitious young indie director named Gus Van Sant and his movie Drugstore Cowboy. 

Drugstore Cowboy (1989) re-contextualised Dillon’s career and provided a mooring point after the drunken sailor’s course it had been following since the mid-1980s. Drugstore Cowboy was a ballsy pitch-black drama set in the early 1970s about a crew of drug addicts led by charismatic anti-hero Bob Hughes ( Matt Dillon) and his wife Dianne ( Kelly Lynch) who spend their waking hours either robbing local chemists so that they can get high or just get high, until a horrific event happens which Bob interprets as a sign that he should get clean. 

I use the word ‘ballsy’ to describe Drugstore Cowboy because at the time of its release the war on drugs in America was very much in full swing, and for a movie that to portray these subjects in the manner in which it did was a truly brave and honest act of filmmaking by Van Sant. The movie neither glamourises being a drug addict nor does it chastise and preach either, it simply presents the characters as a depressing, strange nuclear family that need help which society won’t give them. 

Drugstore Cowboy was a huge critical success upon its release, appearing on multiple best films of the year list and winning four critics’ choice awards. Dillon’s performance was praised by none other than Roger Ebert as “one of the great recent American movie performances”, and he was completely right. Dillon is spectacular in this movie; he manages to radiate charm whilst playing a character who isn’t wholly likeable or pleasant, but thanks to a great script and Dillon’s charisma you come away understanding Bob Hughes as a character and rooting for him in his bid to become sober in the same way you’d root for Renton from Trainspotting.

The success of Drugstore Cowboy should have been a sign to Dillon that his niche was working for interesting indie directors like Gus Van Sant rather than working within the mainstream. Dillon’s first movie post Drugstore Cowboy, the ensemble musical Bloodhounds of Broadway,was a poorly received disaster despite including an all-star cast of Madonna, Rutger Hauer, Steve Buscemi and Randy Quaid which sounds like a Celebrity Come Dine With me line-up from Mars. Dillon would take a year off from acting in 1990 but would return in 1991 starring along opposite Sean Young with the crime movie A Kiss Before Dying directed by James Dearden (the bloke who wrote Fatal Attraction) based on a novel by Ira Levin. 

Whilst A Kiss Before Dying had some champions most notably in Roger Ebert again praising Dillon; “… he is one of the best actors working in movies. He possesses the secret of not giving too much, of not trying so hard that we’re distracted by his performance…”  most other critics weren’t nearly so kind  calling the movie a cliched take on the film noir genre and nominating Sean Young for two Razzie awards. Dillon would then attach himself to Cameron Crowe’s Singles (1992) a movie which can best be described as Hollywood’s attempt to capitalise on the emerging grunge movement in Seattle in the most ‘how do you do fellow kids’ way possible, however it did earn pretty positive reviews and broke even at the box office and has gone on to earn itself a cult following like a lot of Matt Dillon’s filmography.

The years 1993-1994 would see Matt Dillon star in three movies, all of which failed to capture the public imagination. The Saint of Fort Washington (1993) was a feel-good drama about homelessness which saw Dillon alongside Danny Glover in which despite their best efforts couldn’t overcome a clunky script. The Anthony Minghella helmed romance Mr Wonderful (1993) stupidly tried to turn Dillon into a conventional romantic hero, as did John Madden’s Golden Gate (1994) where Dillon played a McCarthy era FBI agent investigating San Francisco’s Chinatown for any suspected communist sympathies -only to inevitably fall in love with Joan Chen. 

These choices look even worse in retrospect when you factor in the fact that Dillon turned down the Bruce Willis role from Pulp Fiction around this time in favour of this row of cinematic non-entities. It really does beg the question of how different Dillon’s career might have been had he said yes to Tarantino, but sadly parallel universes aren’t a thing, so we’ll never know.

What Minghella and Madden failed to understand was that Dillon wasn’t a romantic hero of the Richard Gere variety and casting him in that type of role was akin to putting Haribos in a sandwich. Once again Dillon needed a movie which showed off what he was actually good at, intense character work, which thankfully he would find with another Gus Van Sant movie To Die For (1995). To Die For was a contemptuous satire on the nature of stardom about a small town reporter in New Hampshire named Suzanne Stone (played by Nicole Kidman) who is obsessed with being famous and on tv to a point where she will destroy anything that she sees as an obstacle towards her goal. Dillon plays her happy-go lucky husband Larry, who, despite being constantly side-lined by Suzanne ,genuinely loves and wants to start a family with her, which Suzanne of course sees as an imminent threat to her career ambitions. 

Without going into spoiler territory Dillon gives the part of Larry a ton of charm, stopping him from become just another generic film noir sucker lured into a trap by a femme fatale. Whilst Kidman is undeniably brilliant as the lead (I mean she won a Golden Globe for this movie), Dillon’s understated performance as Larry is what solidifies this movie together as you hope he survives Suzanne’s elaborate psychological manipulations. To Die For grossed $41,000,000 off a $20 million budget which is an excellent return for an adult drama and earned a spate of favourable reviews, but as with the rest of Dillon’s career he failed to capitalise on any momentum which he gained. 

Frankie Starlight (1995), Grace of My Heart (1996), and Albino Alligator (1995) represented another series of misfires by Dillon, but once again he would reinvent himself via showing off his comedy chops. Dillon’s first two comedies Beautiful Girls (1996) and In & Out (1997) were more of a balance of comedy and drama rather than a broad farce. There’s Something About Mary (1998) however was a movie that presented Matt Dillon in entirely new light, because the private investigator character (whom Ben Stiller hires to track down his lost high school sweetheart) that Dillon plays is an absolute top shelf scumbag without a single charming or likeable bone in his body. It helps that the Farrelly Brothers completely destroy Dillon’s movie star looks with the make-up job he was given for the part, gifting him one of the worst moustaches in the history of cinema where he looks less like Errol Flynn and more like a disgraced P.E teacher. 

Taking the role represented a great deal of ingenuity on Dillon’s part because it allowed him to break free from the pretty- boy conventional leading man parts that he was undoubtedly inundated with at this point of his career. There’s Something About Mary was a run-away box office success (it grossed $369 million off a $23 million budget) and earned rave reviews from critics praising the movie’s balance between its gross out humour and genuine heart. John Mcnaughton’s (he of Henry Portrait of a Serial Killer fame) Neo-noir thriller Wild Things wasDillon’s second film in 1998 and played against type in demonstrating that Dillion could capitalise on positive momentum with the movie being a decent hit.  Whilst Wild Things isn’t what I’d call a Blue Velvet or LA Confidential style masterpiece it’s a fun piece of 90s schlock to watch with a few beers and an open mind, a principle which has allowed it to become a cult classic. 

Although I feel like I’m living through Groundhog Day typing this next part, after a loaded 1998 Dillon couldn’t find a movie to follow up his two prior successes with. One Night at McCool’s (2001), Deuces Wild (2002), City of Ghosts (2002), and Employee of the Month (2004) were all about as well received by audiences and critics as a rail replacement bus. The Oscar-bait drama Crash (2004) however provided Dillon’s career with a lifeline. First it demonstrates that he is 100% at his best when he plays against type, with his part in Crash as a racist cop being the most chilling of his career up until that point, earning him an Oscar and Golden Globe nomination and netting him an Independent Spirit Award for best actor. 

Crash is not a good movie in the slightest. It takes a massively simplistic stance on the issue of race in American society, but since this isn’t a review of Crash itself the one thing that you can’t deny is that it made a tonne of money and it somehow beat Good Night and Good Luck, Capote, Munich, and Brokeback Mountain to one of the most undeserved best picture Oscars of all time.  

Dillon’s career post 2004 has fluctuated from the sublime to the ridiculous. While he has done some incredible work during the last decade plus such as in the criminally under-distributed Charles Bukowski adaptation Factotum (2005), a courageous performance in Lars Von Trier’s The House that Jack Built (2018) and a cameo in Wes Anderson’s Asteroid City (2023), for the most part he’s been relegated to starring in movies that are in the 40% range on Rotten Tomatoes ( I’m looking at you Capone, god that was dreadful) and usually play at 1 am on terrestrial television. 

Overall, Dillon has undeservedly had a mixed bag of a career, and while I don’t think he’s entirely to blame, and he definitely could’ve been savvier with his choices. However, I think his not becoming a major movie star was down to the capricious nature of luck rather than a substance abuse issue or being a flighty Brando-like malcontent. Although his career hasn’t panned out the way that it should have given his incredible talent, I’m just happy that Matt Dillon is still out there acting on his terms in movies from which, however terrible they may be, he can gain some sense of fulfilment from them artistically. 


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