Post-300-Insert-Photo-1A decade ago, Jude Law was ugly. Not in reality, obviously — the man looks like he was carved from marble — but he played one of the ugliest characters I have ever seen in a movie.

His name was Harlen Maguire, the photographer/assassin (or would it be assassin/photographer?) after Tom Hanks and his son in the1930s gangster drama Road to Perdition. It wasn’t that Law was just physically ugly — his teeth were yellow and his hair looked oily and thinning  — it was the character himself, the way he moved, the way he looked at people, the way you could see the sick things that were going on in his mind. Sure, it wasn’t too pretty when he got a face full of glass, but the true hideousness of Maguire was more in his personality than the way he looked. And that was all Law’s acting — the audience couldn’t see his good looks anymore; we only saw Maguire.

I was only 14 when I saw Road to Perdition, so it took a few more years for me to realize the oddity of Law being cast as this character. The same man who charmed the panties off countless woman in Alfie, played a sexy robot gigolo in A.I., and was the perfect human specimen in Gattica? The man who, when I saw him live as Hamlet in London in 2009, made the audience swoon as he sword-fought in his bun-hugging linen pants?

That’s the one. He’s made for playing ugly characters. But I don’t think he — or anyone else — fully realized it until now.

Ever since he broke his way into the Hollywood scene with his turn as a golden boy lothario in The Talented Mr. Ripley, Law, purposefully or not, has made his career on being a good-looking actor. His filmography reads like a zeitgeist of female fantasy — lovesick soldier, brooding charmer, sensitive single dad. Recently, however, Law seems to be taking a turn for the unconventional, packing on pounds and receding his own hairline to play roles that, in his younger days (he’s turning 40 at the end of the month), might not have been feasible when his reputation was that of a handsome actor, not necessarily a good one.

Take his role in the latest adaptation of Anna Karenina, for example. When I first found out that Joe Wright was directing a new version, and that Law was starring in it, I immediately thought that he would be playing Alexei Vronsky, the young, rakish cavalry officer who has an affair with Anna.

But Law didn’t play Vronsky. He was Karenin. For those of you who have read the book, you get how weird this is.

“In a weird way, it’s kind of a relief to think, ‘Oh, I know I’m not that young sort of pretty thing anymore,” Law said in a recent story in T Magazine. “It’s quite nice talking about what it was like to be the young pretty thing, rather than being it.”

Leo Tolstoy was not forgiving in his physical descriptions of Alexei Karenin, Anna’s older husband by about two decades. His age isn’t specified, but Karenin would have been in his mid- to late-40s; for Imperial Russian times, he was getting up there. And it would have showed.

Tolstoy repeatedly called attention to singular physical characteristics of characters throughout the novel — Anna’s dark eyes, Vronsky’s teeth, and Karenin’s sticking-out ears, his “weary eyes,” his high forehead, his “whale pelvis and his blunt feet,” his “ugly and sullen” face. None of it was appealing. And even disregarding his unattractive body, Karenin is “morally severe, emotionally barren, piously dutiful, [a] highly controlling pain in the neck of a husband — all Old Testament, no sex appeal,” so writes T Magazine.

“The last thing Tolstoy wanted was for anyone to have a simple, judgmental take on any of the characters,” says Tom Newlin, a professor of Russian at Oberlin College. It was in his class on 19th century Russian love stories, “Love in a Cold Climate,” that I first read Anna Karenina as a junior in college. Newlin says that there is much more to Karenin than Anna thinks there is and judges him for. His great tragedy, after all, is not his nasty habit of cracking his knuckles or his misaligned ears but his rigidity, his set way of thinking and doing. He’s afraid of life.

Karenin is a complex character. He’s a complicated husband. He’s disgusting and sympathetic all at once. And I think Law did a fantastic job playing him, from the hard set of his mouth to the controlled bursts of cold rage.

The idea of a good-looking actor or actress playing a physically ugly character is not anything new. Off the top of my head, I can think of Charlize Theron in Monster, Nicole Kidman in The Hours, Tom Cruise in Tropic Thunder, Heath Ledger in The Dark Knight. And the list goes on. The majority of these actors and actresses, however, were disguised in some way — by fat suits, face paint, bad wigs, or prosthetic noses. They were relying more on their costumes than their own bodies to portray a character.

When Law plays an ugly character, he doesn’t need anything to hide behind. He’s one of a few good-looking actors who can pull off the ugliness on his own (Daniel Day-Lewis, Javier Bardem, and Siobhan Finneran come to mind). He wears fairly normal clothes in Anna Karenina, and although a thick beard partially obscures his face, we can still see his blue eyes, his mouth. Wright has a great quote about working with Law on not doing his “’handsome face’ — raised eyebrows, furrowed brow, wide-open eyes.” And it worked.

We can look past Law’s features and see only the face of the character — old, emotionally stunted, and quite unattractive. Heartbreakingly handsome or not, that is the sign of an immensely talented actor.

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