When Matt Dillon Cosplayed as a New Jersey ‘Waste Management’ Kingpin

It was 1998. There was a new charismatic president in the White House who was yet to exploit interns. Children were routinely chastised for tending to Tamagotchis during school hours. Any band that was Irish could score a number one. Things were good.

And, in LA, and though not nominated for anything, a then 34-year-old Matt Dillon arrived at the 70th Annual Academy Awards. Famous people did that, because, back then, the Oscars felt legitimately important, and the afterparties weren’t sponsored by CBD brands. He arrived with former girlfriend Cameron Diaz who he met on the set of There’s Something About Mary, and her only nomination for the evening was to hand out the very important best sound gong. And yet despite the dearth of professional acknowledgement, here was Dillon (and Diaz) with all the vim of two wide-eyed Hollywood freshmen with best actor already in the bag: all excited, and all dressed up.

It’s easy to think of it as just another snapshot of ‘simpler times’ destined for a second half-life on a throwback Instagram account. But, on the eve of The Sopranos’ debut season, Dillon preempted The Culture’s fascination with middle aged American men that quietly intimidate others outside of New Jersey pizzerias, before Scorsese’s Irishman forced us into a state of moral penance and reckoning, and way before Tony Soprano’s torts ever tied him in knots. This is waste management exec at its finest.

There’s a gesture to a tux, but it’s not a tux. Not really. While satin lapels undoubtedly kept clipboard-wielding Academy jobsworths at bay, the suit is boxy, billowy, designed to elongate shoulders and fill doorways with much menace at 4am. The tie is cleaved at the end, a blunt object made of casino banquette fabric. And, though Dillon’s black shirt would eventually go on to garb unreasonable provincial door staff, it’s enjoyed a second wind because it looked genuinely good the first time round – and it’s the sort of head-to-toe monochrome that, whether rightly or wrongly, abets the glamorisation of Italian-American heavies. Bad things happen in exceedingly good Versace baroque shirts.

What makes Dillon’s unsung outfit such a sleeper hit is the lengths to which it bucked the trend. While there’s much to be said for the sense of ceremony an Affleck-Damon penguin suit musters, Dillon took a risk when guys weren’t really taking all that many risks. In the Nineties, there wasn’t a rethinking of black tie, or a relaxation of dress codes, or Timothée Chalamet. Like almost everything else back then, menswear was a cloistered affair that couldn’t just let go of the Old Ways. It was open to change, yet still unwaveringly taut. It played by the rules. It didn’t upset anyone – but the Very Famous Men still turned up, and in a golden age of celebrity participation, Dillon turned it out.

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