Assessing a filmmaker’s legacy can be difficult, especially when his career hasn’t ended yet. It can be even tougher when that director’s personal life has in some ways outdistanced his movies, warping our impression of them just as it’s changed our feelings about the person who made them.

Most filmmakers carry around a sort of thematic baggage with them—the collective, accumulated assumptions about their work that we take into the theater with us—and it’s perhaps most damaging when it comes to Woody Allen’s movies. Outside of staunch fans like myself, it seems like practically nobody goes into his films anymore with much goodwill or high expectations.

And, frankly, why should they? Some think the prolific writer/director currently averages about one good movie for every five films he makes—and maybe that’s being generous. Even then, the personal stuff shines through: Whether it was the dissolution of his long-term relationship with Mia Farrow and his eventual marriage to Farrow’s adopted daughter Soon-Yi Previn—which staunch fans have to remind everyone was not his daughter because the impression still lingers more than 20 years later—or the recent return of Farrow’s allegations that he sexually abused their adoptive daughter Dylan when she was just a girl, Allen bears a toxic, icky patina in the eyes of many.

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Of all modern filmmakers, Allen is probably the most self-deprecating artist to be confronted with such scandals. When someone like Roman Polanski faced sexual abuse charges, the grand, mournful, sometimes sinister undertones of his later films allowed viewers—if they wanted—to assume that he was, at least subconsciously, addressing the accusations, perhaps offering a peek into his mental state. Whether that was accurate didn’t matter: Polanski’s penchant for dark thrillers and bold dramas felt, culturally, like an artistic defense or acknowledgement of the alleged past crimes, giving his films more resonance because of the collective assumptions we put on them.

But Allen? There’s no such grandness to his films, which he’d be the first to acknowledge. Every time he’s out promoting his latest comedy or drama, he’ll say something along the lines of “I always have such high hopes for whatever I’m working on, and it always turns out to disappoint me.” He constantly laments that he’s never made a film that can compare to those of the European masters he loves like Ingmar Bergman, culturally as imposing and titanic a filmmaking figure as we’ve ever had. So when he puts out little doodles like To Rome With Love or a Magic in the Moonlight—and because he puts them out so quickly, one after another after another—we as a society only get more irritated with him. His films are slender, unassuming things, and yet that toxic cloud around him is so serious and, for many, deeply troubling. The modesty (and, admittedly, the hit-or-miss quality) of his recent movies seems to work against him in the public square. The impression appears to be, “How can he make such frothy comedies—even one most folks like, such as Midnight in Paris—when he’s accused of such terrible things?”

Which is why I want to get back to this legacy question—and his latest film, the intriguing, mostly successful drama Irrational Man. For much of Allen’s later career, he’s been seen as the once-funny guy who was a big deal way back in the 1970s and ‘80s, but who eventually turned to more serious movies and stopped making the kind of silly films of his earlier career—and, then, eventually just became irrelevant as an artist as he continued to mine the same Upper West Side/white privilege milieu until he vanished into his own navel and whatever European country would give him the best deals to make movies overseas. That’s the cultural impression of Allen, and it’s hard for staunch fans to argue most people out of that belief—especially when he hasn’t helped us out by making a movie as great as Annie Hall or Manhattan in quite a while.

But time has a way of changing impressions, and I wouldn’t be surprised if Allen’s legacy gets a reevaluation, probably sometime after he dies. (He turns 80 in December.) Even assuming that the tabloid-attracting aspects of his personal life will attach to him permanently—and, I can only hope, the sexual-abuse charges are untrue, which is not to diminish the clear anguish they still cause Dylan and other members of Farrow’s family—I think that Allen’s later filmography will, in retrospect, be judged more favorably, or at least with a little more curiosity, than it does now. The culture has wanted Allen to stay the deft, wistful romantic who saw New York in widescreen black-and-white. But movies like Irrational Man are so compelling because Allen has been more and more interested in the gray areas. It’s not just that Woody views the world as bleak and unfeeling, entirely dependent on such vagaries as chance and luck: It’s that he’s not sure why we aren’t all driven mad by that knowledge.

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Irrational Man—like Crimes and Misdemeanors, Match Point and Cassandra’s Dream—is a movie built around a murder. Because the movie’s trailers are being a bit cagey about an important plot point, I suppose I should throw in a Spoiler Alert here. The film concerns Abe (Joaquin Phoenix), a disillusioned philosophy professor who feels that his life has no meaning and that his high-minded musings don’t make any difference in a godless, senseless world. But the morose sad sack finds a new lease on life in the strangest of ways: Overhearing a distraught woman at a nearby table at a restaurant complaining about an unethical judge who’s giving full custody of her kids to her no-account husband, Abe decides that killing this judge is the only humane thing to do. After all, the judge is corrupt, the husband is a deadbeat, and the wife is the only person who actually loves the kids: This isn’t murder but, rather, a deeply moral act, right?

The way Abe goes about his act and learns to live with the consequences—and how his relationship to an adoring college student (Emma Stone) intensifies because she’s aware of his act—powers the rest of Irrational Man. The emphasis on dialogue that freely quotes from Kant and other famous philosophers gets tiring—and there are other Allen tropes that are equally distracting—but the core ideas (a godless universe and our helpless reliance on chance) have plenty of juice, proving to be the driving force of his movies for a good long time. In fact, they’ve been the guiding light of Allen’s output since he moved away from his ‘70s/’80s heyday.

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That doesn’t seem like a coincidence. Even as Allen was becoming a decorated filmmaker for 1977’s Annie Hall, winning Oscars and also enjoying relatively good box office—remember, that was also the year of the mammoth blockbuster Star Wars, which it beat for Best Picture—he demonstratively took no interest in outward success, expressing misgivings about accolades in general. “If you accept it when they say you deserve an award, then you have to accept it when they say you don’t,” he said in 1974. As for his talent, he’s equally dismissive. “Talent is absolutely luck,” he told his biographer Eric Lax around the late ‘80s, echoing a line his character says in 1979’s Manhattan. “People worship talent and it’s so ridiculous. Talent is something you’re born with, like Kareem [Abdul-Jabbar] is born tall.”

He then added, “The two things that I wish are that I had courage, which I don’t feel I have, and that I was born with religious faith. Those two things would be great. I’d probably need less courage if I was born with religious faith. But if I was born with those two things, I’d be very far along in the game.”

Faith (or, really, lack of faith) is a key component in Allen’s films. His critics complain that his movies’ pessimistic worldview is merely lazy nihilism. On the occasion of Magic in the Moonlight, which is partly about the battle between faith (expressed through the existence of magic) and reason, Variety critic Justin Chang complained, “Industrious though he may be, there’s something about Woody Allen’s God-is-dead shtick that brings out his laziest instincts as a writer: It’s as if he’s trying to make a point that’s already such a foregone conclusion, he needs to expend only minimal effort to get it across. But if that’s the case, why keep telling us something he’s already told us many times before? At a certain point, doesn’t all this relentless insistence begin to sound like an increasingly desperate form of denial?”

I think that’s exactly right—and that’s exactly Allen’s point. In Irrational Man, as he’s done with so many of his recent films, Allen obsesses over what he perceives to be the meaningless of existence by creating a character who decides to test out his filmmaker’s hypothesis. Murder doesn’t just give Abe a sense of purpose—it’s a fight against the void. Speaking at Cannes, where Irrational Man premiered, Allen said, “If you look at people… people need something to believe in, in their lives. They have to choose whether life is going to be meaningful or meaningless. People will choose religion in their lives, for example, and will make an irrational choice. They think that if they live a good life, they will die and go to heaven. That’s no less crazy a thought than Abe thinking that if he commits this act, his life will suddenly turn around for the better. As long as there’s something dedicated you believe in, you make a choice and you go with it. That’s the way that I see it.”

People in Allen’s movies rarely do despicable acts because they’re evil, but only after committing them do they see the world in a much broader, richer context. Not that it always helps: Judah (Martin Landau), the adulterous murderer of Crimes and Misdemeanors, rediscovers his long-lapsed Judaism after the killing, but ultimately learns not to let his conscience bother him. “In reality, we rationalize, we deny, or we couldn’t go on living,” he advises Woody’s character near the end of the film.

Judah is luckier than Terry (Colin Farrell), one of two brothers in Cassandra’s Dream that commits a murder, only to be torn apart by guilt that ultimately leads to his and his brother’s (Ewan McGregor) demise. Perhaps Allen’s coldest killer is Chris (Jonathan Rhys Meyers), a former tennis player who looks at the world in stark terms: “The man who said ‘I’d rather be lucky than good’ saw deeply into life. People are afraid to face how great a part of life is dependent on luck. It’s scary to think so much is out of one’s control.” That he gets away with killing his secret lover (Scarlett Johansson) only validates that grim assessment: The ball could have very easily bounced the other way. In a sense, Allen isn’t arguing that God is dead—he’s trying in vain to find something akin to a belief in God that will make life seem worth living.

Chance and individual morality play their parts in Irrational Man as well, but even Allen’s comedies more and more often wrestle with this inescapable bleakness. Celebrity looks at how show-biz success is very much a product of good or bad breaks. Melinda and Melinda tells the same story as both a comedy and a drama, suggesting that the fate of Radha Mitchell’s title character is entirely dependent on one’s perspective. In Vicky Cristina Barcelona, two friends (Scarlett Johansson and Rebecca Hall) have very different ideas about happiness, their destinies shaped partly by their choices and partly by luck. You Will Meet a Tall Dark Stranger—spoiler, the stranger is the Grim Reaper—is all about making choices in the hopes of finding happiness in the face of the inevitability of death.

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The value of Allen making so many movies is that it gives us a snapshot into his almost daily thought process. And for the last 25 years or so, these particular questions have eaten away at him, so it’s no surprise that they keep popping up in his films. It’s not hard to imagine that part of the reason they have is that they’re a genuinely darkening reflection of the way he sees his own success and his own inability to find true contentment. All those years ago, he flirted with the idea of titling Annie Hall the far less catchy Anhedonia, the clinical term for the inability to experience pleasure. That title would fit on just about every film he’s made since.

When Allen used to star in his movies, he would endlessly insist that his ineffectual onscreen self wasn’t anything like the focused, driven businessman he is. (You have to be both businessman and artist if you’re going to be as independent a filmmaker as he’s been.) But now that he’s ceded the spotlight to other actors, it’s much easier to see his characters as parts of his psyche, specifically the part that worries that nothing much matters. Irrational Man doesn’t resolve those conflicted feelings because Allen himself hasn’t resolved them. I suspect he never will.

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But for anyone who shares his misgivings about a world that pretends to be moral but so often behaves otherwise—a world in which a search for meaning (whether through religion or art) sometimes seems like a massive feat of self-delusion—Allen’s movies aren’t fashionably nihilistic or a broken record; they’re an articulation of a shared daily struggle. Because of Allen’s tabloid incidents—and because each of his recent movies is constructed with a melancholy shrug rather than as a bold, masterful declaration—it’s hard to see this. But when the book on Woody Allen is written long from now, I think this core aspect of his artistry will finally get its due. People aren’t going to stop wondering what it all means anytime soon.


Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.