Back to IndieWire

The 10 Best Male Characters In Woody Allen’s Films

The 10 Best Male Characters In Woody Allen's Films

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 featuresAnother 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.”

David Shayne (John Cusack) and Cheech (Chazz Palminteri) in “Bullets Over Broadway” (1994)
It was almost inevitable that we’d end up with an entry with more than one performer from one movie, and given the density of excellence in the cast of “Bullets Over Broadway,” this was always an obvious one to pick. In the last couple of decades, Woody’s attempts to tackle broader, straight-up comedy have mostly been lacking, which might make “Bullets Over Broadway” his most recent fully successful non-drama: the film’s a bouncy delight, and perhaps a good argument that Allen should work with a co-writer (in this case, friend and collaborator Douglas MacGrath) more often. The cast (which includes the likes of Rob Reiner, Tracey Ullman, Edie Falco, Jack Warden and Jim Broadbent alongside the Oscar-nominated Jennifer Tilly and Dianne Wiest, the latter of whom won) is sterling across the board, but it’s John Cusack and Chazz Palminteri that we particularly want to single out here. Cusack (in his second team-up with the writer/director after “Shadows & Fog” a few years earlier) has the role that Allen would have played a few decades earlier, the young, idealistic Clifford Odets-ish playwright forced to compromise his art. But while many might have simply imitated their director, Cusack channels his own nervy, anxious energy into the role, creating something distinct. It’s one of the actor’s best performances, and one feels a bit for Zach Braff, who had to fill his shoes in the recent Broadway musical version. But Palminteri (probably still best known for “The Usual Suspects,” which he landed soon after this) might be even better: the actor plays Cheech, the seemingly thuggish bodyguard of Tilly’s character, who turns out to have a surprising capacity for drama, and becomes Cusack’s ghostwriter. It’s a fun set-up, and Palminteri runs with it: a hint of a wink or nod and it would have fallen apart, but he plays it dead straight, without nodding to gangster-movie cliche, and is all the funnier for it. Like Tilly and Wiest, he was Oscar-nominated.

Dr. Ross (Gene Wilder) in “Everything You Ever Wanted to Know About Sex (But Were Afraid To Ask)” (1972)
Comically bearing the same name as George Clooney’s “E.R.” character, Gene Wilder’s turn as Dr. Doug Ross is the star role in the second segment of Allen’s vignette-based loose satirical adaptation of the huge bestselling sex book. Along with the famous final segment, in which Allen plays a sperm, the second segment is the funniest and most successful of the otherwise patchy film’s seven sections, a lot due to Wilder’s absolutely genius underplaying as the doctor who falls for a sheep. Plotting a course from rational disgust and incredulity as a prospective patient reveals that his problem really is that Daisy, the sheep he is in love with, no longer loves him back, to lovesick fretting, to consummation over the course of just a few minutes, it’s a one-joke sketch that Wilder and Allen manage to find new ways to make funny and daft and perverse at every turn. In fact, the loaded, excruciatingly extended silence with which Dr. Ross greets the Armenian shepherd’s initial explanation of “I’m in love with a sheep” is a thing of beauty all itself. It’s also a very uncharacteristic moment for an Allen film, which are generally more known for having characters constantly gabble out their reactions and emotions verbally, so it shows just how much this is Wilder, or maybe just how early on this was in the more experimental phase of Allen’s work (it was his fourth directorial film). As the skit progresses towards its inevitable “climax,” the comedy becomes more situational than character-based, but it’s a mark of just how great Wilder is here that he ever manages to imbue “guy falling in love with a sheep” with any sort of personality, let alone an oddly soulful, and, dare we say it, romantic one. Bestiality has never been so tenderly, humorously drawn.

Elliot (Michael Caine) in “Hannah And Her Sisters” (1986)
It’s a long way from Michael Caine‘s South London birthplace to Woody Allen’s Manhattan, but it’s a testament to Caine’s brilliance as a performer that he fits right into the filmmaker’s milieu, despite the turn being a world away from the Cockney charmers he made his name with, and the film won him his first Oscar, for Best Supporting Actor, for his troubles. “Hannah And Her Sisters,” one of Allen’s very best, sees Caine play Elliot, the husband of Mia Farrow‘s titular Hannah, who begins an affair with her sister Lee (Barbara Hershey). Caine dials down his natural and considerable charisma to make his character a slightly drab individual (not the easiest task for a performer to do while remaining watchable), but one who’s livened up by his extra-marital shenanigans. There’s something pathetic about Caine here, in a way that would have been positively unthinkable when you saw “Get Carter” or “Alfie,” and yet the actor somehow lets you into the man’s head, and makes him, and his late-in-love discovery of passion, if not likable, than at least understandable. Indeed, his monologue on Lee’s virtues is one of the most memorable, and beautifully performed, in all of Allen’s work. Caine has such an established persona (“you were only supposed to blow the bloody doors off” et al.) that his enormous powers of subtlety are often overlooked, so it’s wonderful that he was recognized for something as relatively minimal, but finely tuned, as this.

Danny Rose (Woody Allen) in “Broadway Danny Rose” (1984)
Almost inevitably, lists of best characters become lists of best performances and vice versa, but one case in Allen’s filmography where the distinction is somewhat made clear is with Danny Rose in his 1984 paean to the fading days of theatrical talent agents. Purely judged on Allen’s performance in the role, Rose is great fun but perhaps nothing particularly special within the canon, but it’s how he is drawn outside of those contours, refracted through the prism of his modest legend, that makes the character so much more than just Woody in a bad check suit shilling for his latest balloon-folding act or whatever. In particular Rose is fleshed out by the anecdotes shared by the Greek chorus-style collection of comedians, meeting in the Carnegie Deli to swap stories about the old days—days that Rose, with his relentless goodhearted enthusiasm for his vaudeville-level talent acts, unmistakably belongs. So while structurally the film may most resemble the kind of comedy gangster caper that Allen often hangs his plots on (which incidentally gives an against-type Mia Farrow a rare opportunity to be genuinely funny as the trashy gangster’s moll), as so often, Allen’s heart lies elsewhere. Here, unusually, it’s with his lead male, the endearingly hapless, selfless Danny Rose whose unbounded admiration for his z-grade acts (“Never took a lesson! She’s self-taught!” he mouths breathlessly about his water-glass-player) is both the subject of the film’s funniest lines, and its most touching aspect. As much a love song to the odd nobility of living in bygone glory days as “Midnight in Paris,” and quite a bit funnier, “Broadway Danny Rose” is among the most loveable, if not the most essential of Allen’s films, a lot because of the uncomplicated, sincere sweetness of Rose himself.

Tom Baxter (Jeff Daniels) in “The Purple Rose of Cairo” (1985)
Never quite attaining matinee idol status himself, Jeff Daniels nonetheless did a pretty good job of embodying idol-dom in Allen’s classic romance in which a film character comes alive, steps down from the silver screen and falls in love with a mere mortal, and a mousy one at that. Tom Baxter is the character in the film-within-the-film with whose black-and-white image Cecilia (Mia Farrow) falls in love, in that escapist, fickle way that we all fall in love with movie stars. But as he enters the real world, Daniels, aided by the skilful writing, makes Baxter literally 3-dimensional, his naivete about this strange, harsh Depression-riven place and time proving both refreshing and romantic, and ultimately untenable. And the love he feels for Cecilia, while it might seem like everything she’s ever wanted, of course it can only be a shadow, a projection, because she is real and he is a movie. The undervalued Daniels negotiates the playing of this character quite brilliantly, as much as he is all dash and sincerity and hunkiness, there is always an insubstantiality to the character, thrown all the more into relief when the actor who originally played Baxter, Gil Shepherd (also played by Daniels, of course) comes onto the scene. Considering it’s a fantasy romance in genre, “The Purple Rose of Cairo” has a surprisingly pessimistic denouement, but it’s hard to see any other way it could have turned and still feel so wise and true, because Daniels isn’t just playing a movie character, he’s playing The Movies made flesh, everything they do for us, and everything they trick us into believing. So of course our instinct is for the happy ending that “the movies” promise, but just as Cecilia discovers when she chooses Gil over Tom, it’s better to experience heartbreak for real than everlasting happiness as part of a fantasy. It’s Tom’s fate to live out the latter, however, and Daniels makes us feel that tragedy, as he sadly goes back to his perfect movie life, just as much as Cecilia’s.

Ted (Alan Alda) in “Manhattan Murder Mystery” (1993)
We could easily have chosen Alda’s first collaboration with Allen, in 1989’s “Crimes and Misdemeanors” for this list. But since we’ve already called out the amazing Martin Landau from that film, and since Alda’s riffing on a somewhat similar character here (at least in terms of what the Woody Allen character thinks of him), and mainly since we’re always going to take the chance to shine a light on the terrific, undervalued “Manhattan Murder Mystery,” we’ll go with Ted. Alda is seemingly Allen’s go-to guy for an attractive, successful love rival of whom Allen himself, here playing publisher Larry, is both jealous and a little disdainful, and his Ted is the apotheosis of that. And yet, for all his flaws, Alda imbues Ted with such charm that we can understand Larry’s wife Carol (Diane Keaton) falling for him a little bit too. In fact, it’s a sign of the writer Allen’s fondness for all his characters here that Ted gets a few hero moments of his own, as the central foursome, including Larry’s own crush/client Marcia (Anjelica Huston), join forces to solve the murder next door. It’s one of Allen’s most purely enjoyable, fizzy films, dotted with astute one-liners and genuinely funny situations (the tape recorder phone conversation is a terrific ensemble character/comedy moment) and Ted is an unusually well-drawn and sympathetic take on what would easily be the fifth wheel in a lesser film. But this is not just one of mid-period Allen’s best films, it’s also one of his most balanced, and Ted and Marcia’s eventual pairing off, as Larry and Carol discover that the murder was just the spark they needed to reignite their marriage, is hugely satisfying. Plus it’s Ted, as played by the handsome, urbane Alda, who gives rise the best self-deprecating last gag in any Allen movie, as Larry/Allen pooh-poohs the notion he was jealous with the line “Ted? You’ve gotta be kidding! Take away his elevator shoes and his fake suntan and his capped teeth and what do you have?” To which Carol/Keaton zings back “You!”

Jack (Sydney Pollack) in “Husbands And Wives” (1992)
One of Allen’s best and most focused works, “Husbands And Wives” was overshadowed at the time (and to some extent now) by the events in the director’s personal life: his relationship with Mia Farrow fell apart during filming on her discovery of nude photos he’d taken of her adopted daughter Soon-Yi. This leaves uncomfortable, abrasive echoes throughout the film, in which Allen and Farrow’s fictional surrogates break up, in part because of his flirtations with a much younger woman (Juliette Lewis). But it’s the other husband and wife of the title, Judy Davis and Sydney Pollack, who are the fascinating heart of the film. Davis, quite rightly, won most of the plaudits and awards nods for the film (and she made the cut of our best female performances list last year), but Pollack’s a fine dance partner for her. The late filmmaker was best known as a director, but had started as an actor in the 1960s, and made a memorable cameo in his best film, “Tootsie.” But “Husbands And Wives” kicked off a late-blooming run of acting gigs that would go on to include work with Kubrick, Frank Darabont and Tony Gilroy, and it’s no wonder why: a sort of Ghost of Christmas Future for Allen’s character, he begins the film announcing his split from Davis’ Sally, and soon runs off with a younger woman, only to change his mind after discovering Sally’s own affair. The two eventually reconcile, but it’s hardly a happy reunion, being one of the most pointedly bittersweet conclusions in the director’s career. Pollack has an easy, naturalistic screen presence, both warmly paternal and fearsomely patriarchal, and the verisimilitude of his mid-life crisis fits perfectly with the raw hand-held docudrama feel that Allen gives the movie.

Of course, with a filmography the length of Allen’s, not to mention a propensity for densely-populated ensemble casts, there are more than a few other male characters who might have made the grade on a different day. Most notable by their absence, perhaps are Javier Bardem as Juan Antonio in “Vicky Cristina Barcelona” and Allen himself as Isaac in “Manhattan.” Elsewhere Tim Roth made a surprise showing for “Everyone Says I Love You,” but again the sheer disposability of that project rather counted against him, while Ian Holm’s Ken in “Another Woman,” which is also a great turn, just missed out on a top spot too. And of the many Allen surrogates over the years, the one we were closest to including in addition to John Cusack’s David, was Owen Wilson as Gil in “Midnight in Paris”—he brought a refreshingly genuine naivete to the part that made it his own, only occasionally seeming like he’s aping Allen.

And there are a few smaller characters in Allen movies over the years that have made deep impressions on us too, though we deemed their screen time or overall impact within the film too small to challenge the bigger parts above (even Wilder is the the lead in his particular segment, after all). But those that missed the cut on these grounds included Adrien Brody’s few short minutes (“I see… a Rhinoceros!”) as Salvador Dali in “Midnight in Paris” along with co-star Corey Stoll’s rambunctious turn as Hemingway. Max von Sydow’s Frederick in “Hannah and her Sisters” is a terrific Allen archetype: the chilly, didactic emotionally distant, brilliant man who inspires devotion but knows less how to love than how to lecture. Chiwetel Ejiofor is a rare person of color in an Allen film, and unfortunately it’s “Melinda and Melinda,” which is more a semi-successful thought experiment than a satisfying film. But Ejiofor is nonetheless memorable as soulful composer Ellis Moonsong, the catalyst for the love-triangle complications that occur during the “tragedy” portion, while Christopher Walken is pretty much unforgettable (also unspellable: he’s “Wlaken” in the credits) in a sliver of a role as Annie’s comically lugubrious brother in “Annie Hall.” But probably closest to shading an entry on the list proper was Gene Hackman’s turn as Larry in “Another Woman.” Against type for the actor, Larry is sensitive and steadfast and passionately devoted to Gena Rowlands’ Marion, and given only a scant couple of scenes we understand deeply just how much she missed out on when she rejected his sincere advances.

So which of Woody’s men are you raging that we missed? Make your case, preferably via the medium of a pithy, quotable, Allen-esque one-liner or two, in the comments below.

Sign Up: Stay on top of the latest breaking film and TV news! Sign up for our Email Newsletters here.

This Article is related to: Features and tagged , , , ,

Get The Latest IndieWire Alerts And Newsletters Delivered Directly To Your Inbox