Matt Dillon's 50 Most Memorable Scenes
movies matt dillon tv
Garin Pirnia
For his fiftieth birthday
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Esquire
Today actor Matt Dillon joins fellow quinquagenarians like Nic Cage and Brad Pitt in turning the big 5-0. Dillon started acting as a teen in the late '70s and has clocked over 50 credits in a wide range of genres, most notably mainstream roles in There's Something About Mary, Wild Things, Crash, and Singles. But unlike his aforementioned contemporaries, Dillon's never succumbed to starring in a franchise or any summer blockbuster action films, which is incredible thinking he could totally helm a superhero flick. He's opted for more indie fare in the past decade, but this summer he'll make a major comeback when he stars in his first TV role, the M. Night Shyamalan-produced Wayward Pines series on Fox. We look forward to seeing what he does with primetime, but in the meantime, we celebrate Matt Dillon as we've come to know him, from crop top-wearing lost teen to bonafide ladies man.

Over the Edge (1979)

At fifteen years old, Dillon made his film debut. Dillon's Richie sports sleeveless crop top shirts and other questionable fashions from the late '70s.

"A dead kid..."

"Steers and queers"

Many think the line about Texas and steers and queers originated from Full Metal Jacket, but it was actually Dillon who first said it in this film. (An Officer and a Gentleman used it a second time in 1982.)

Little Darlings (1980)

He flirts with Kristy McNichol in a charming way. Then he takes her virginity.

My Bodyguard (1980)

Dillon turns the tables and plays a greasy bully. He gets bonus points for wearing white pants while trying to intimidate someone.

Tex (1982)

The first in a trio of S.E. Hinton/Francis Ford Coppola collaborations he starred in, this was Dillon's first lead role.

Tex broods because his brother sold his damn horses.

But he feels better after setting his arts and crafts on fire.

The Outsiders (1983)

So much young talent: Dillon with Cruise, Macchio, Estevez, Howell, and Lowe.

Here, he packs a powerful punch.

Yet he can be a little clumsy.

Rumble Fish (1983)

Rusty James's brother teaches him about Siamese fighting fish.

The Flamingo Kid (1984)

In the mid-'80s, Dillon got goofy. Here, he makes eating annoying.

Dillon shares a scene with babelicious Lucille Bluth (Jessica Walter). Who knew she was once so ripped?

More eating issues: Dining on rich people food can be difficult.

Target (1985)

Dillon pals around with his dad (Gene Hackman), who turns out to be a spy.

A fleeting action star is born. Dabbling in international espionage, he and his dad save his mother from being blown to bits.

Kansas (1988)

Look at that badass swagger! He owns this mediocre film.

That gold tooth warns others not to mess with him. He is a dangerous criminal, after all.

He's also a violent gum chewer.

Drugstore Cowboy (1989)

Keeping with the outlaw mindset, Dillon won an Independent Spirit Award for his portrayal of a pharmaceutical robber/drug addict in probably Gus Van Sant's best work.

Hats... so many hats.

Seriously, don't get near any hats on a bed or else. Don't mention puppies either.

A Kiss Before Dying (1991)

Overall a terrible film, but Dillon gets to strangle people and then a train runs over him at the end, resulting in an unintentionally funny denouement.

Singles (1992)

In grunge-era Seattle, Cliff's the lead singer of band Citizen Dick, along with Pearl Jam members Eddie Vedder and Jeff Ament, and Soundgarden's Chris Cornell. The flowing mane, the soul patch... so vintage.

Composing bad Citizen Dick songs.

Installing glass-breaking speakers.

Cliff learns to appreciate Bridget Fonda. Again, with the hats.

"Bless you," Cliff says.

If you stop being an egotistical musician and start being polite, you'll get the girl.

The Saint of Fort Washington (1993)

Back to drama: Dillon plays a homeless schizo photographer who hears voices and eventually gets stabbed to death. Speaking of being murdered...

To Die For (1995)

Being sexy has its price, as he'll find out later when Suzanne "Crazy Eyes" Stone (Nicole Kidman) hires Joaquin Phoenix to whack him.

"Put your face on me," he demands.

Until the day he dies, he's an avid supporter of his nutty wife, though.

Beautiful Girls (1996)

We feel your pain, Matty.

In & Out (1997)

Dillon went platinum blond to play a pretentious actor.

Cameron Drake inadvertently outs Kevin Kline during an acceptance speech at the Oscars. Dillon didn't win any awards for this, but Joan Cusack did receive an Oscar nom for her role.

There's Something About Mary (1998)

The film was Dillon's biggest hit, and it won him an MTV Movie Award for Best Villain.

Channeling Dr. Teeth.

"Puffer, stay away from the light!"

While trying to resuscitate Mary's dog, Dillon accidentally sets Puffer on fire.

Wild Things (1998)

Dillon has a threesome with Denise Richards and Neve Campbell, which is probably the only thing people remember about this movie — besides the Sapphic pool scene, of course.

Well, and Bill Murray as his lawyer.

And Dillon and Kevin Bacon sharing a brewskie, with homoerotic undertones.

One Night at McCool's (2001)

There's a Village People joke in here somewhere. Believe it or not, Dillon plays the most normal dude.

Matt: "Do you like water?"

Liv Tyler: "I love it. It's actually my second favorite thing in the world."

Matt: "Really? Then what's your first favorite?"

Liv: "Fking."

Crash (2004)

Say what you will about Crash beating out that gay cowboy movie for Best Picture, but Dillon's performance as a cop cinched him a much-deserved and overdue Oscar nomination.

Employee of the Month (2005)

After doing the intense Crash, Dillon lets loose and goes postal at his bank job.

Then he turns down hooker Jenna Fischer's many advances.

Modern Family (2011)

In a rare television appearance, Dillon guests as Claire's (Julie Bowen) limo-driving ex-boyfriend, who's romancing her mother (Shelley Long).

In the end, a man's gotta have a code.

Girl Most Likely (2013)

But sometimes that code involves wearing a rubber suit so you don't get struck by lightning for the fourth time.