WARNING: SPOILERS

It’s a little ironic that after his successes with spaghetti westerns and “Hang ‘em High,” Hollywood’s attempt to bring Clint Eastwood into the modern age feels more dated than any of those 19th-century dramas.

I get what they’re trying to do: take Clint’s cowboy, make him a modern lawman, and tell a fish-out-of-water tale about extraditing a prisoner from New York City back to Arizona. Smart. Coogan shows up in string tie and cowboy hat, way taller than anyone around him, unable to blend in, with everyone assuming he’s from Texas. Even when he politely corrects them, they still say Texas. That’s a good recurring bit.

I also like the luggage routine. The cab driver tells him his briefcase counts as luggage, which is 50 cents extra, while the hotel clerk has a different view.

Clerk: That’ll be $7. In advance.
Coogan: The sign says $5.
Clerk: $7 without luggage.
[Coogan places briefcase on desk]
Clerk: That ain’t luggage.
Coogan: There’s a cab driver in this town that’ll give you an argument.

Good line reading from Clint, too. It’s more amused shrug than angry rube. He’s not being taken for a ride; he knows what’s going on but figures “When in Rome…”

Except, oddly, when it comes to police bureaucracy. The prisoner he wants, Ringerman (Don Stroud), has taken LSD, and is now incarcerated in the prison ward at Bellevue, which means another layer of bureaucracy he has to get through. His gruff NYC contact, Lt. McElroy (Lee J. Cobb), tries to lay it out for him. First, Coogan needs a doctor’s OK to get Ringerman out of Bellevue. Then he has to check papers with the DA’s office. Finally he has to go to the NY Supreme Court (?!) so a judge can render him into his custody.

Instead, Coogan sneaks Ringerman out of Bellevue and tries to spirit him out of the state. But at the airport he’s clocked by one of Ringerman's men—David Doyle of “Charlie’s Angels” of all people—and Ringerman gets away. Now Coogan has to track him down, with the higher-ups in both NY and AZ agin him.

None of this is particularly dated. And I’m not really talking about the hippies he encounters, either. That’s just the time period—like flappers in the ’20s or preppies in the ’80s. There’s a scene where Coogan enters a hippie nightclub, with everyone dancing and grooving to Hollywood’s awful version of what 1967-68 rock music is supposed to be, and with Coogan a head taller than the swirling bodies around him. You anticipate something great—like Robocop or Terminator in a nightclub, or when Eddie Murphy goes looking for Billy Bear in a country-western bar in “48 Hrs.” But I got the sense the filmmakers were less interested in culture clash than bringing in the youth market. “Hey, hippies! It’s you guys, look: dudes with long hair and chicks with words painted on their bodies! So come see our movie!” At one point, a near-naked woman swings over to Coogan on a trapeze (you remember those in nightclubs), slides into his arms, and says, “Hey, groovy! …  Ooh, looking for anyone special?”

And that’s the dated part. Not the lingo. The sex and the sexual politics. Coogan has one job to do, extradite Ringerman, but he keeps getting distracted. By girls.

OK, so it's the lingo, too.

Pigeon-Toed Orange Peel
The movie opens a bit like the opening to “For a Few Dollars More“: an unseen rifleman from a high position watches an approaching rider. Here, the rider is in a Jeep. It’s Coogan, and the man in the high position is an escaped Navajo native, who’s thrown away the accoutrements of modern living (jeans, shoes) and apparently wants to live the natural life like his ancestors. Did he commit a crime? Not sure. But for some reason it’s Coogan’s job to bring him back.

After he’s got him in custody, though, Coogan gets distracted. He stops off at the home of a beautiful married blonde for a little nookie. And it’s there, mid-bath, mid-cleavage joke, that his superior finds him and barks at him about the NYC gig.

In NY, the romantic interest is Julie Roth (Susan Clark), whom Coogan first spies outside McElroy’s office in a busy, gritty 23rd precinct. She’s talking to Joe (Seymour Cassel), who’s well-groomed, wearing a suit, and sitting at a desk. Joe mentions the brooch pinned to her chest and touches it. And again. And insinuates. She responds: “Next you’re going to ask me if I make it with all the good-looking fuzz around here,” adding that nothing he says or does will upset her. That’s like an invite. And he takes it. He cops a feel. And again. And when he ignores her polite remonstrations, our hero, Coogan, intervenes. He tells Joe to back off. When Joe doesn’t, Coogan slaps him around.

Which is when Julie gets mad. At Coogan.

Turns out she’s not a cop (as Coogan assumed), and Cassel isn’t a cop (as I assumed). No, she’s his parole officer. And I guess she thought the gentle touch-my-breast approach might mother him into reforming? Who knows? It’s post-sexual revolution but pre-women’s lib, which is a bad period. It's all a little icky.

And it gets worse. After defending her from sexual assault, Coogan does everything he can to get in her pants. She keeps resisting, but with a smile, half caving in. It’s like that until two-thirds of the way through, when she tells him off. Sure. Except at the end, with no reconciliation scene, there she is, waving frantically from the rooftop of the Pan Am building as he flies off. Poor Susan Clark. What a thankless role.

Anyway, Ringerman is on the loose.

So after everyone says “Go home, Coogan,” Coogan questions Ringerman’s mother, Ellen (Betty Field), but apparently blows the cover of a cop pretending to be a junkie. How he blows the cop’s cover, we can’t fathom. Then it’s another date with Julie, where, rifling through the file cabinets she happens to keep in her living room, he discovers the address of Ringerman’s far-out hippie chick, Linny Raven (Tisha Sterling), and leaves to question her. Oddly, not at her pad. This is the scene at the trapeze-swinging nightclub, “The Pigeon-Toed Orange Peel”; and it’s only after a confrontation in a back room (with Albert Popwell, the “I gots to know” guy in “Dirty Harry”) that Coogan takes Linny back to her pad, where, again, he forgets about his job. They make out. Sex is implied. Then it's 4 AM and she takes him to a pool room to meet Ringerman. It’s a set-up: It's Ringerman’s gang, all of whom look like rejects from a 1950s B-movie.

At least we finally get a good fight—admittedly with that fake, too-red blood of the first post-production years. When Coogan can’t get David Doyle to talk, he returns to Linny Raven’s place and smashes a fist into her wall. That’s the move that finally jangles free Ringerman’s hideout: Fort Tryon Park in the Heights. They walk there. Gunfire is exchanged, there’s a foot chase, then a motorcycle chase, and Coogan, after so many women, finally gets his man.

Are lessons learned? Yes! From both sides in the culture wars. Bidding farewell on the rooftop of the Pan-Am building, Lt. McElroy finally remembers Coogan is from Arizona. As for Coogan? In the beginning, he’d crushed a cigarette beneath his boot rather than let the Navajo take a puff. Now, in the helicopter, he offers a cig to Ringerman. He even lights it for him. So I guess Coogan realizes that perps are people, too.

That, or he’s racist.

Where have you gone, Willie Mays?
1968 was a tough year to make a Hollywood movie. The Production Code was dead, the studio system was in shambles, the culture was shifting so much that nothing felt solid to the oldsters running things. Three years later, Eastwood and his first-time director here, Don Siegel, would navigate it all better, or at least with a particular point of view, in “Dirty Harry.”

You know what might make a good triple feature? “In the Heat of the Night,” “Coogan,” and “Midnight Cowboy.” Three fish-out-of-water stories from three years in a row: big city cop in the country (1967), a country cop in the big city (1968), and a country gigolo in the big city (1969). Do we try this anymore—navigating this clash of American cultures—or have things worsened too much to even attempt it?

Betty Field impressed, by the way, as Ringerman’s mom, so I had to look her up. She made her name on Broadway in the 1930s (“Boy Meets Girl,” “Room Service”), while her turn as Henry Aldrich’s girlfriend in “What a Life” led to the Hollywood adaptation of same, opposite Jackie Cooper. She played the first screen version of Curley’s doomed wife in 1939’s “Of Mice and Men,” and Daisy Buchanan in the Alan Ladd “Great Gatsby.” In the 1950s, she played moms: to Kim Novak in “Picnic,” to Hope Lange in “Peyton Place." She was also the Grace of Grace’s Diner in “Bus Stop.” She kept doing theater throughout. She’s good here. Her character has layers.

Love the location shooting. That whole “helicopter from JFK to the Pan Am Building rooftop” is a great slice of New York history. You can read more here. It began in 1965, stopped by the time “Coogan” was released, started again in 1977. Then an accident led to five deaths and there went that. Helicopter service over Manhattan traffic is now just for celebs.

During the final chase scene, did they include Coogan’s Bluff—former site of the Polo Grounds—among the shots? I assume so, but probably in the background. It’s still not a bad title, even if the location doesn’t figure in and the man doesn’t bluff much.

Lesson learned.