Is it that time of year already? This week, 2014’s Woody Allen film opens. “Magic in the Moonlight” (review here) sees the director back on the frothy-fun-in-foreign-climes form that he’s made a stock in trade recently, after the deviation of last year’s “Blue Jasmine.” That film’s Oscar-winning central turn by Cate Blanchett led us to discuss some of Woody Allen’s best female characters, and if it’s unlikely that “Magic in the Moonlight” will prove the same awards-magnet for any of its cast, there’s certainly enough here to warrant another riffle through Allen’s back catalogue of performances. And with our reviewer calling attention to Colin Firth in particular, who, cast a little against type, “drives his incorrigibly cranky character right to the edge of unsympathetic” but pulls it back just in time to save his sarcastic and cynical illusionist from all-out detestability, perhaps it’s as good a time as any to take a look at Woody’s men.
If Allen is rather more famous for the quality of his female roles than his male roles (possibly because it’s an unusual thing for a male writer/director to be so often so female-centric; possibly because so often he himself has played the male lead in his films, or has had a proxy stand in for him, and that comes with its own host of associations), his constant through-line has always been the push/pull dynamic of heterosexual relationships. And that has led, along the way to some startlingly good, unusual roles for men—often as foils to a central towering female performance or two, but no less insightful and nuanced for that. Here are ten of our favorite male characters in Woody Allen films, each contending in their different ways with professional anguish, unrequited love, philosophical quandaries, aging, marital infidelity or, most relatable of all, falling for a sheep.
Emmet Ray (Sean Penn) in "Sweet & Lowdown" (1999)
By the late 1990s, the sincere, sometimes controversial figure of Sean Penn didn't seem like a natural fit with Woody's work, but the result was magical enough that it makes us long for the pair to team up again. The role of Emmet Ray, a reasonably well-known, heavy-drinking, scumbag of a jazz guitarist whose life is continually overshadowed by that of his idol Django Reinhardt, was originally penned by Allen (under the original title of "The Jazz Baby," back in the early 1970s) to be played by the writer/director, but after nearly thirty years in a drawer, went to Penn (though Johnny Depp was also reportedly considered). And it's hard to imagine anyone better: Penn brings a mix of swagger and deeply insecure neuroticism that makes him very much a creation of Allen, but one that doesn't simply echo the filmmaker in the way that so many of his leading-men surrogates ended up doing. Thanks to a rather self-regarding, humorless public persona, it became easy to forget over time that Penn broke through with a performance of true comic genius in "Fast Times At Ridgemont High," and got to stretch those muscles for the first time in a long while (and, bar a handful of exceptions like "This Must Be The Place," they haven't been stretched since) as Emmet, and his deft, fleet-footed comedy skills are something to behold here. And yet the film certainly falls on the "drama" side of the divide rather than the "comedy" one as there's a real melancholy to the image of the self-destructive artist (it feels like a precursor to "Inside Llewyn Davis" in more ways than one). "Sweet & Lowdown" has a number of things to recommend it—gorgeous photography by Zhao Fei, sensational music, a wondrous, entirely silent supporting turn by Samantha Morton (like Penn, Oscar-nominated)—but Penn and Emmet Ray might be the highlight.
Judah Rosenthal (Martin Landau) in “Crimes and Misdemeanors” (1989)
More frequently occupying a kind of bittersweet, ambivalent register, it’s actually rare that any successful Allen film truly deals in despair. But if we define despair as the absence of hope, redemption, and justice, and a worldview in which depravity and deceit are not only unpunished but seem the best way to get ahead, “Crimes and Misdemeanors” may just be one such. And Judah, as played brilliantly and uncompromisingly by the great Martin Landau, is the central pivot for all that darkness. While Allen himself, Mia Farrow and Alan Alda all appear in a second, more comedic but no less pessimistic strand of the film (one that was included at the behest of a studio who didn’t want another straight-up, uncommercial downer like Allen’s previous two features “Another Woman” and “September” on their hands), Judah is defiantly the black heart of the story. A successful ophthalmologist who arranges the murder of his mistress when she threatens the stability of his professional and family life, Landau is fearless in embodying Judah’s rottenness, yet never neglects the subtleties of the characterization either: his hypocritical mock-outrage when his brother Jack (a brilliantly cast Jerry Orbach) first suggests the murder that Judah of course wants to bring about; his deceitful philosophizing with the kindly rabbi Ben (Sam Waterston), designed purely to give himself the satisfaction of believing he’s a moral man. But really his character, and the film, is all about ego. The second story has its more exaggerated, comic take on that in Alda’s brilliant portrayal of the successful ninny Lester, with Judah as the kind of snake who’ll not only kill to protect the façade of his social standing and get away with it, but who will, even more cynically than that, be able to justify it to himself. It’s a perfect, and perfectly convincing portrayal of a monster—an obscenely everyday monster.
Alvy Singer (Woody Allen) in "Annie Hall" (1977)
These days, Woody Allen's a relatively rare presence on screen: he's only starred in two of his films in the last decade ("Scoop" and the equally disappointing "To Rome With Love"), and acting-only gigs as in this year's "Fading Gigolo" are even rarer. But there was a time early in his career when the idea of anyone other than Woody Allen starring in a Woody Allen movie was almost unthinkable, with the actor, like Chaplin's little tramp, generally riffing on his established persona to one degree or another. As time went on, he found new notes to play, but probably his finest Woody Allen As Basically Woody Allen performance came in the film that, hardly coincidentally, was probably his most personal and textured up to that point—the remarkable "Annie Hall." Marking the passage from his Early Funny Ones (though it's still as flat-out hilarious as anything in his filmography) to more serious fare, Allen plays Alvy Singer, a thinly veiled version of himself as he unpacks his childhood and previous relationships through his love affair with quirky hat-sporter Annie (Diane Keaton). Until now, Allen's on-screen presence had mostly been as a sort of a runt of the Marx Brothers litter, but partly thanks to the formal playfulness (including direct-to-camera address), there's something deeply confessional and vulnerable about the performer here, and it's about as likable as he's ever been on screen (the icky age difference in the central "Manhattan" relationship hampers that one, for instance). By making the film so firmly about him, Allen found his voice, and in turn, his most defining role. Other good turns were to follow (see below), but this one is the genesis not just of Allen's following performances, but also everything from "Seinfeld" to "Louie."