Gentry: The Soulful, Sleazy Bureaucrat at the Heart of Drugstore Cowboy

My time in the Army knocked the wanderlust right out of me. I understand there’s a difference between traveling the world under-orders and traveling to see the sights, but there’s just something in my body, maybe my Circadian rhythms, that constantly screams I’m good right here, thank you.

One day, I might get the bug again and set out on the road, but until then, I mostly prefer to bring the world to me rather than going out to meet it. That I don’t have a lot of money to go globetrotting probably makes it a lot easier to resist the temptation.

Still, I find it important to keep my German limbered after being stationed in Germany to make sure my fluency doesn’t decay to where I can do nothing but ask where the bathroom is. It took me a lot of hard work (plus student loans on top of my G.I. Bill) to attain that fluency, and it’s not something I’m eager to let slip.

I have a lot of different tricks for making sure my Deutsch doesn’t go to shit without having to return to Germany. Some are obvious, like workbooks or flashcards. Others are of more recent vintage, like the HelloTalk app I use with a woman in Germany, with whom I’ve been translating English poems into German and vice-versa (it’s good to do creative exercises as well as practical ones).

Chief among my techniques is to watch movies I love, but in German. I’ve accumulated a nice little library of Region 2 Discs that sits upstairs at home on a bookshelf below a collection of my German-language books. There’s a lot of Die Simpsons DVDs on that shelf, but after a while, I started to notice that if I watch nothing but cartoons, even good ones, a kind of manic, aggravated energy seeps into my consciousness. It becomes exhausting, kind of like a long shift babysitting your sister’s rambunctious kid.

I still love The Simpsons, but I make sure to mix in some feature films, mostly longish pictures that reward rewatching, movies that also happen to be my favorites in English. I’ve got Once Upon a Time in America, Sergio Leone’s unwieldy, beautiful and graphically violent magnum opus about Jewish gangsters; I’ve got Andrew Dominik’s The Assassination of Jesse James, a real puzzle box of a film with stellar performances from Brad Pitt and Casey Affleck, about fame and mythmaking and jealousy.

And I’ve got Drugstore Cowboy, Gus Van Sant’s blackly comic road movie about junkies in the Pacific Northwest. The main characters spend most of the movie trying to stay high and manage to, thanks to the fearless leadership of charismatic hophead “Bad” Bobby Hughes, played with frenzied brilliance by Matt Dillon.

It’s a great movie on its own terms, filled with action (lots of brushes with the law and other lowlife criminals) and cool but unobtrusive cinematic techniques (there are a ton of inserts and closeups). It’s photographed in a nice aquamarine palate; blues and greens and blue-greens, turquoise and topaz hazes lain over thickets of shaggy firs after heavy rains that leave the hills misted. The color scheme doesn’t only fit the wet arboreal clime of Washington State; it hints at the mint-green walls of motels and institutions like prisons and hospitals where Bobby and his band matriculated and are destined to return (unless they really roll snake eyes, and wind up dead).

I typically don’t pay close attention to set design, but, like I said, I’ve watched these movies quite a few times, and after a number of viewings, I’ve started to pick out more granular details.

One of those things that becomes more and more foregrounded the more I watch Drugstore Cowboy is the performance of character actor James Remar, as Gentry.

For those not familiar with the movie’s plot, a lot of the film consists of a cat-and-mouse game between Bobby and his lunkheaded crew versus Gentry and his pack of roughhouse cops. Just as Bobby’s underlings don’t piss or fart without his say-so, Gentry’s fellow cops mostly look to him for cues about when to get rough or when to lay back and hope Bobby manages to snare his own foot.

Gentry’s character in the movie is played at two separate tones: one for when Bobby is on his tear through every drugstore and dispensary in the Pacific Northwest; the other, very different tone is struck after Bobby breaks good, casts aside the needle, and starts working the Program and a square gig.

In the first half of the movie, Gentry’s a bit saurian and menacing. He slams Bobby against walls and seethes as he makes threats and jabs a finger in the skinny addict’s face. He asks to see Bobby’s arms, ostensibly checking for track marks, but with a kind of rapine hunger that makes him look more like a vampire trying to find a good vein to suck.

Even at his worst, though, Gentry exhibits an exasperated weary moral core. It may be on the point of being permanently poisoned by his dealings with shitheads like Bobby, but it’s there. It’s a very subtle humanity, mostly concealed. Gentry knows he cannot afford to show too much of what he actually feels, lest he end up manipulated by the kinds of master sociopaths who operate on the other side of the law. Like Ethan Hawke’s cop in Training Day, he has learned to hide his smiles and cries. That he can suggest them to the viewer, even when ostensibly playing into the trope of dickhead cop, is a testament to the actor’s fine skillset.

At one point, when his squad is raiding Bobby’s crash pad looking for dope, Gentry points the finger at his antsy quarry and shouts, “Just when I thought Bobby Hughes was flying straight, bam! You knock off another drugstore.” He may only be hoping Bobby flies straight because the kid is such a headache, but he’s still pulling for Bobby.

In the same scene, as the cops begin tossing the apartment looking for dope, Gentry responds to Bobby’s plea for him and his crew of cops to please not smash his golf clubs. “They’re Ben Hogan’s, man.”

Gentry breaks Bobby’s balls about him having a good handicap solely because he confines his play to public courses (“public courses are for pussies”), but he does indeed spare Bobby’s clubs. Considering that Bobby would find a way to hide dope in a nine-iron if anyone could, Gentry’s intervention can be read as gullible rather than purely compassionate. It’s the risk any cop runs, though, when cutting a guy a break without receiving something in return.

Later, when Bobby does swear off dope after a bad experience on the road, he settles down in Portland once more. He begins a routine of working (he operates a punch press) and attending group meetings. At some point, Gentry begins to take notice of him again. He spots Bobby walking past the restaurant where the detective’s having a coffee. Gentry looks off pensively, almost wincing as if he’s confused by his own compassion for the ex-con, ex-junkie who it turns out really is trying to fly straight this time.

A short time later, Gentry comes to warn Bobby about a plot to kill him hatched by a fellow cop. Gentry recognizes that he has to let the mask slip, and the guard drops as he says words to the effect that he doesn’t want to see Bobby hurt. He no longer looks as if he’s trying to conceal his concern for Bobby, but as if he’s hidden his smiles and cries for so long now that there’s no way for him to communicate his feeling for the kid. If anything, Gentry looks a bit confused by the prison he’s constructed for himself as a defense against the world of cops and robbers. It’s always threatened to snuff out his last spark with its unyielding cynicism, but now that Bobby has fanned that spark into a bit of a flame by bucking the odds, Gentry seems ill-at-ease. The writer and former addict William Burroughs (who makes an appearance in Drugstore Cowboy as a defrocked priest) once said that when you’re on heroin, your emotions shut down and all you feel are your literal urges. That has to be part of the appeal of the drug; not just the euphoria that comes with shooting (especially after a long delay), but the simplification of life into a procrustean cycle of shoot-eat-sleep-repeat.

Gentry, as a longtime narcotics cop, is enveloped in a similar, soul-deadening caul, one born of bureaucracy though rather than hard drugs. He has grown accustomed to his cynicism, if not becoming outright addicted to it.

In a way, Gentry is the fulcrum upon which Bobby’s tale turns.

Bobby, you see, is heavily beholden to superstition throughout the film, fearing to leave a hat on a bed or to view the reverse side of a mirror. As an addict, he sees himself mostly as a plaything of destiny. He outwits the cops and gets high only by the grace of a capricious god who might one day turn on him and leave him high and dry, to kick cold turkey in a dark prison cell.

Later, when Bobby gets sober, he discovers his own agency (since it was him, and not some spell or mojo that got him clean). His view of the world becomes less dark, fatalistic. The aquamarine palate that made Portland look like a dewy fish tank in desperate need of a cleaning has yielded to a warmer honey-brown. It paints Bobby’s fire escape outside his dingy apartment with a rich amber during sunset, dapples his path with gold when he strolls through the park with Tom the Priest.

And just as the colors soften, Gentry’s look does, too, confirming Bobby’s suspicions that the universe is not totally fickle and arbitrary and will give back to you what you give to it. Gentry has changed his behavior toward Bobby because Bobby has changed as a man.

For a seemingly small role by a character actor, it’s a hell of a lot to convey. It’s a doubly heavy burden when you consider that Gentry does it all with his eyes and what he doesn’t say (because his code as a lawman will not allow him to betray such emotions or doubts).

As mentioned before, the role of Gentry is played by James Remar, a guy I recognize mostly from a couple of peak Walter Hill movies. He plays a baddie in 48 Hours, a sleazed-out and scruffy criminal who’s a little closer to one-dimensional; in The Warriors, he plays the horndog tough whose quest for tail means he’s one of the boppers who doesn’t make it to Coney Island at the film’s denouement. (He ends up handcuffed to a park bench by a young and vivacious Mercedes Ruehl, which frankly does not seem like much of a punishment.)

He also appears in more mainstream fare, and may have even been a leading man once or twice. I think he was in one of those women-dating-in-New-York shows my sister watches.

He’s always been handsome, even moreso as he’s gotten older and his features have thinned into harder angularity, a la Jeff Bridges, but he can also play oleaginous and menacing. He’s charismatic, but exudes a weird combination that makes him, like Willem Defoe, someone with a lot of sexual power and gravitas that’s both magnetic and off-putting.

Gentry seems to be a one-off in the actor’s canon as he’s kind of anodyne, mostly by the book, and rarely seen without a tie. A lot of those inserts that Gus Van Sant includes among his directorial touchstones are very close shots of the square knot (or is it a Windsor?) on Gentry’s tie.

His personality seems to lack a sexual component, and if there is a woman in his life, it is probably a wife from whom he is estranged or toward whom he feels compassion rather than passion. The estrangement could be literal, like a divorce. Or it might be the kind of sad and silent truce that grows up between two people when they occupy the farthest corners of a shared bed and their only common ritual now is a half-hour of television before turning in.

Anyway, it’s a great performance, and I might have never noticed it had I not watched the movie a couple hundred times in German. And for those wondering, the title of Drugstore Cowboy in German is Drugstore Cowboy.