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The Last Great Sean Penn Movie

The Oscar-winner’s latest directorial effort, ‘Flag Day,’ is a dud. Better to revisit ‘The Pledge,’ which was released 20 years ago and deserves a second look — both as a subversion of the whodunit and an example of Jack Nicholson at his very best.

This weekend, Sean Penn unfurls Flag Day, his sixth film as a director, which stars him and his real-life daughter Dylan in a domestic drama about a young woman coming to grips with her con-man dad. It’s an earnest study of the bonds between a parent and his child — and how that child can’t help but adore her old man, even if he’s really hard to love. It’s also, unfortunately, pretty bad — the sort of movie that mistakes tortured emoting for having something to say. Flag Day is actually Penn’s second straight dud, following the 2016 debacle The Last Face, which was practically laughed off the screen when the press saw it at the Cannes Film Festival. (I was there — it was a trainwreck.) 

Not that long ago, Penn seemed to have a promising filmmaking career ahead of him. Already established as one of those “best actors of a generation” actors — Oscar nominations, the respect of his colleagues, the air of an impassioned artist and someone who takes activism seriously — he attacked directing in a similar way, telling difficult, brooding stories in, well, a pretty difficult, brooding way. You don’t go to a Sean Penn-directed film for a few laughs. He means to put you through the emotional grinder and, for a while, he did it superbly — just not recently. Lately, all that self-seriousness has calcified into swaggering, macho ponderousness meant to bowl you over with its strenuous gravitas. I’ve rarely been as exhausted as I was after seeing The Last Face and Flag Day — all that imposing misery made me want to take a nap.

It’s now been 20 years since Penn made his last great film. I know that 2007’s Into the Wild has its champions — I’m fond of it, too — but by his demanding standards, the bittersweet story of Christopher McCandless (Emile Hirsch), who travels cross-country to find himself, was as close to a crowd-pleaser as Penn would ever allow himself. To really get a sense of what Penn can do behind the camera — challenge his audience while delivering an utterly gripping, uncompromising tale — I’d recommend checking out The Pledge. If you’ve never heard of it, you’re also missing out on one of Jack Nicholson’s finest performances.

The film introduces us to Jerry Black, a detective about to retire. Lots of cop movies are about an older guy who’s one day away from retirement — he can’t wait to get out of this job! — but Jerry isn’t one of those guys. Truth is, he’d really like to keep working, so it’s probably not a surprise that, during his going-away party, there’s news of a murdered young girl, Ginny, that sparks his interest. He tags along when the police go to the crime scene. And when he tells Ginny’s parents what happened, her heartbroken mother (Patricia Clarkson) makes him swear he’s going to find out who did this. Jerry isn’t ready to hang it up and go fishing somewhere warm, so he pledges he’ll find the culprit.

This century has had its share of great, subversive murder mysteries — at the top of the heap is Zodiac, an obsessive thriller about obsessive men who spend their lives chasing a killer they never find — but The Pledge is one that ought to be mentioned in the same breath. If the title doesn’t ring a bell, don’t feel bad: That’s due to the shoddy treatment Warner Bros. gave the film, releasing it quietly in January — the time of the year on the movie calendar when studios jettison their worst fare while audiences are busy watching Oscar-bait. The Pledge didn’t deserve that — although, to be fair, it’s far from a commercial slam-dunk, even if on paper it sounds like a traditional whodunit. But Penn and Nicholson (who had previously starred in Penn’s second directorial effort, 1995’s The Crossing Guard) don’t go down any obvious paths. Finding the killer is important to Jerry, but not as important to him as holding onto something he knows he’s losing.

It’s better not to reveal too much of the plot, but here’s all that matters: Quickly, the cops get their man, a Native American with an intellectual disability (Benicio del Toro). But after he kills himself, Jerry starts to wonder if maybe there was a rush to judgment — maybe the killer is still out there. His superiors tell him to let it drop — after all, he’s retired, this isn’t his problem — but he can’t. He made this promise to the girl’s mother. He has to see this through. What good is a man’s word if he breaks it?

One of the remarkable things about The Pledge is how it turns genre tropes on their head — specifically, this fallacy of the honorable detective who will stop at nothing to get justice for an innocent victim. A greater cultural recognition of police brutality in recent years has helped correct that self-aggrandizing narrative, but 20 years ago, a movie like The Pledge was undermining it in its own way. Nicholson’s rogue detective is presented as a hero — and then Penn slowly deconstructs that illusion, eventually showing Jerry to be someone clinging to his status in order to delay the inevitable irrelevance he’ll feel once he really has to retire. The Pledge is a movie that’s often described as being about obsession, and that’s certainly true — as you’ll discover, Jerry goes to some dark extremes to apprehend who he thinks is behind the crime — but his drive isn’t wholly righteous. It’s more about proving to himself that he hasn’t lost a step — that he’s still got it. There’s something self-pitying about his dogged determination. He wears his pledge to the mother like a crown of thorns. 

Jack Nicholson in The Pledge

Other movies Penn directed have drowned in their self-martyrdom — his characters are draped in anguish, practically whipping themselves to illustrate how despondent they are — but in The Pledge, there’s a genuine attempt to interrogate that tendency, both within Penn and in his characters. At his peak, Nicholson was an extraordinarily compelling actor — you loved his rebelliousness, the sense that he was an electric shock in human form — and because he always came across as vital and virile, it was disconcerting to see him age on screen. Tellingly, a year after The Pledge, he starred in About Schmidt, which was a more melancholy comedy around essentially the same premise: a lonely older guy who doesn’t have anything now that his career is over. Nicholson is so commanding that you initially root for him in The Pledge — Jerry is clearly smarter than his colleagues — but then the movie strips away what we usually admire about such characters. After a while, we’re not sure how to feel about Jerry: He’s supposed to be the good guy, but there’s something selfish about his obsession. Is he doing all this for Ginny? For her mom? The answer gets murkier as The Pledge goes along.

If this movie (which featured a murderers’ row of incredible supporting players, including Aaron Eckhart, Helen Mirren, Robin Wright, Vanessa Redgrave, Mickey Rourke and Sam Shepard) is Penn’s last great one as a director, then it’s also very close to Nicholson’s last great one as an actor. He still had About Schmidt and The Departed to come, but in terms of powerful dramatic roles, The Pledge is a fine farewell, if indeed he is truly done with acting. Much like Penn, Nicholson was often cited as one of the best — if not the best — actors of his generation, and also like Penn he explored masculinity in all its complexity, giving us thorny men wrestling with powerful demons. He could be incredibly charismatic, but he also played monsters

Jerry is more muted, as if the man is all spent up, with little left to give. But he wants to keep going — he cannot ponder a life after his job. And so Jerry looks and looks for the killer. The Pledge might remind you of a movie Nicholson made years earlier, Chinatown, which was also about a sharp guy who’s convinced he’s going to get to the bottom of things. His character in Chinatown doesn’t get exactly what he wants, and neither does Jerry. For all its bleak examination of obsession and aging, The Pledge is the exact opposite of Penn’s recent dirges. It doesn’t put you to sleep — it jolts you awake. 

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