The Last of Robin Hood

Samuel Goldwyn Films

In Maleficent, Angelina Jolie recreates her iconic curse with such perfect charisma that it’s a big letdown when she changes tune about 2.5 seconds later as Disney strives to make her relatable. Our beloved villainess became the reactionary scorned woman, and all of that potential for more evil cackles flies out the window.

Thinking about this terribly missed opportunity for excellent evilness, I couldn’t help but think about the many real-life, often larger than life names who have been immortalized in cinematic biographies in ways more bittersweet than satisfying. It’s great to see them and get the rush of their performance, but sad to watch it wasted on an inferior film, or a bit part in someone else’s larger whole.

Kevin Kline as Errol Flynn

Kevin Kline was born to play Errol Flynn, but for years no one jumped at the opportunity – until Kline was in his sixties, and already over a decade older than the swashbuckling actor was when he died. As a result, there was one story left to tell – The Last of Robin Hood, a romance about his final days as he courted teen actress Beverly Aadland (Dakota Fanning).

Flynn was a massive celebrity and a controversial man, one whose acting, addictions, and repeated scandals with underage girls are ripe for a tell-all biopic, but the salaciousness is secondary to the perfection it would’ve been to get Kline at the right age. He is the spitting image of Flynn, with the same charisma that made jumping from stage to screen so smooth. And, of course, Kline played an icon pirate of his own: the Pirate King of Penzance.

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Meryl Streep as Julia Child

Every moment of Meryl Streep as Julia Child in Julie & Julia is wondrous. She managed to not only apply her formidable acting talents, but also believably morph herself into the iconic cook, her 5’6” frame stretching not only by camera trickery, but how Streep carried herself.

Unfortunately, she’s only half the story, and no amount of acting could help Amy Adams make Julie Powell as compelling as the woman whose 91 years were full of worlds and adventure as a writer, OSS researcher, and culinary revolutionary. It didn’t help that her rapport with Stanley Tucci’s Paul Child even made the thought of a Child w/ Child conversation movie preferable to an extra-exasperated and exasperating cinematic embodiment of Powell.

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Christian McKay as Orson Welles

On one hand, it’s hard to argue against Me and Orson Welles, because it introduced me to the talents of Zoe Kazan. However, it’s easy to forget that and wish that McKay’s Welles had gotten a full film, and not one he had to share with Zac Efron – a feature about theater more than the icon.

As Roger Ebert once described it: “The impersonation of Welles by Christian McKay in Me and Orson Welles is the centerpiece of the film, and from it, all else flows.” In a great performance, an actor doesn’t only embody the real person they’re playing – they also find a way to tap into the charisma and make us want more. McKay as Welles brings the actor/filmmaker back to life and every scene is an extra moment with Welles – a way to cheat death. If only cinema was daring enough to bring his one-man play on Welles, “Rosebud: The Lives of Orson Welles,” to life.

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Janet McTeer as Mary McCarthy

Hannah Arendt

Zeitgeist Films

In her excellent piece on Mary McCarthy and Hannah Arendt’s friendship, Michelle Dean questions McTeer’s stint as the writer in Hannah Arendt: “The results are not good. McCarthy, played by Janet McTeer, is blowsily silly – and though she could be wicked and subversively funny, McCarthy was far from silly.” Nevertheless, McTeer brought life to the film, and thinking about an evolution beyond what Dean calls the “flat portraiture” of popular female friendship makes the thought of a full-length McTeer role all the more enticing.

With the silliness tamed – and that’s certainly within McTeer’s talents – there is much to mine, and intellectual deliciousness to devour. McCarthy held controversial opinions and wrote of big events like Watergate and the Vietnam War, penned novels that included “The Group,” had enduring friendships with women like Arendt, and fought a long feud with Lillian Hellman, which inspired Nora Ephron’s play “Imaginary Friends.” McTeer’s talent has been itching for a juicy, starring role, and playing McCarthy full-stop could be it.

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Cate Blanchett as Katharine Hepburn

There are no shortage of tasty cameos in Martin Scorsese’s The Aviator, but exactly one performance sticks in my head ten years after its release: Cate Blanchett’s Katharine Hepburn. As a once-partner of Hughes, Hepburn gets more than a quick cameo, but her infectious enthusiasm is still shackled in the story of a troubled man.

What Blanchett makes of her supporting role was enough to win her a well-deserved Oscar. The actress melts away behind the dark lipstick and recognizable Hepburn drawl, and the glimpses into the woman behind the celebrity – the energy, the interactions with her family – are magnetic. When she finally breaks things off with Hughes, to be with Spencer Tracy, I want to follow.

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Corey Stoll as Ernest Hemingway

A lot of people have embodied Ernest Hemingway over the years, but none with quite the same gruff magnetism as Corey Stoll in Midnight in Paris. He doesn’t so much melt away into Papa, as he just gets him, and makes the performance all about the charisma he exudes – so much so that it becomes irrelevant what he looks like.

His Ernest is tasked with a spiel of Papa-isms that try to boil his work into a few lines, but Stoll makes them work; he makes them natural. One begins to sense Hemingway’s presence and impact rather than just enjoying a glimpse at old greats. Where someone like Clive Owen played Ernest, Stoll seemed to channel him.

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Penn Badgley as Jeff Buckley

This is my qualified entry. I still maintain that Mark Rendall was born to play Jeff Buckley, and Badgley was a strange choice. And it might seem even stranger to include a character that is the focus of their film on this list. However, Jeff Buckley isn’t really the focus in Greetings from Tim Buckley. It is a story of Jeff only so much that he is Tim Buckley’s son, much like Maleficent is the story of her interaction with the human world – not her life as a fairy.

But in a few fleeting moments, when Badgley’s Jeff was allowed to riff and not face the angst of a famous and absent father, the beauty that would lead to Buckley’s “Grace” bleeds through and the Gossip Girl star vanishes. In one scene, he goofs around in a record store, his musical joking beginning to take an ethereal shape of its own, from teasing to melody. The hints of what’s to come are exciting, before the story once again silences his music. In another scene, we get the most fleeting taste of “Grace” as he begins to become a musician in his own right, sketching the music that would make him famous. But, again, it is a mere moment in a larger whole.

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