Ranking Jude Law’s 10 Best Performances: ‘A.I.’ to ‘The Holiday’

Richard Shepard’s black comedy/crime drama isn’t for everyone, as it’s purposefully abrasive and asks you to spend 93 minutes with a whole series of unsavory characters. But Law is completely committed from the opening (filthy) line to the character of Dom, a safecracker who spent 12 years in prison after refusing to sell out his boss. Violence and mayhem abound (along with the threat of castration), but Law seems to be having a blast with a no-holds-barred turn you can’t take your eyes off.

Law was already known as more than a pretty face when Steven Spielberg cast him as “Gigolo Joe,” a “male pleasure Mecha” a.k.a. sex robot in this ambitious sci-fi parable set in a futuristic society. Joe is an expert at seduction, a charmer who can look people right in the eye and lie convincingly. Everything about Joe is smooth and graceful, from his artificial skin to the cap of hair that seems to lock into place like a Lego. When Joe begins caretaking an 11-year-old Mecha child named David (Haley Joel Osment), his commitment is both deeply human and determinedly robotic.

You can feel the weight of the world on the shoulders of FBI agent Terry Husk, who led the investigation of a neo-Nazi group called the Order. Though events took place in 1983, the film could not feel timelier as Husk is determined to stop the rise of white supremacy before it becomes a socially acceptable norm. Husk is haunted by his own demons. He’s estranged from his wife and family and carries the burden of years of difficult cases — and the emotional scars are etched all over Law’s face. Husk gets off to a slow start; there are times you’ll wonder if he’s actually up for the job. But that’s the fascinating part; it’s a touching performance in a genre that tends to glorify such characters.

Like every British actor before him, Law was at one time rumored to be in the running to play James Bond — though he denies he was ever offered the role. While we never got to see him hold 007’s martini, the action-comedy gives us something better: Law as Bradley Fine, a suave super-agent who is also totally oblivious to the fact his partner Susan Cooper (Melissa McCarthy) is madly in love with him. An early scene finds Bradley giving Susan a velvet box — a token of his appreciation — only to reveal the ugliest cupcake necklace known to man. “It’s a crazy cupcake!” Fine chortles, bugging out his eyes and holding up his hands like claws. It’s somehow seductive and hilarious all at once.

Though it launched countless memes, Paolo Sorrentino’s big, bold and nasty series never got the proper attention it deserved. Perhaps the image of a Coke-swilling, narcissistic leader drunk with absolute power who surprisingly ascends on the highest title in his domain hit a bit too close to home in early 2017 when the first series premiered in the states on HBO. Still, Law’s performance as the titular Pope Pius XIII is mesmerizing — even when he spends the majority of the second series, the 2020 follow-up, “The New Pope,” in a coma. Despicable and malevolent, Law understands the key to all bullies: they believe they are the victims.

Law likely had plenty of personal experience to draw on for his role as the manipulative talent manager to Natalie Portman’s pop star in Brady Corbet’s underrated gem. But as a sleazy opportunist who just might be the literal devil, the actor wanted to avoid the typical tropes and cliches. So he drew inspiration from both real-life producer Robert Evans and Ben Gazzara’s character in “The Killing of a Chinese Bookie,” a desperate man trying to maintain a façade of charm. Law shows the appeal of selling one’s soul for fame and fortune, but also nails the seedy underbelly.

Shortly after directors Spielberg and Anthony Minghella cast Law as the model of male perfection in “A.I.” and “The Talented Mr. Ripley,” respectively, the actor decided to upend expectations by playing Harlen Maguire, a Depression-era freelance killer. Designed to evoke a rodent, Law is seen early on hunched over a cup of coffee with sickly pale skin and a deeply unsettling grin full of rotting teeth. (Apparently even Law hated his look and wore a hat to disguise his thinned hairline whenever he wasn’t shooting.) Everything about him is cruel and unpleasant. It’s not just his physical appearance — it’s the determined and dispassionate way Maguire goes about executing his subjects and the clear fascination he displays watching them expire.

Though nothing overtly supernatural occurs in Sean Durkin’s moody marital drama, there is something dark and unsettling about it. (There is also an old country manor, a dead animal and children acting out, so one can be forgiven for expecting a literal ghost story.) Instead, Law and Carrie Coon play Rory and Allison O’Hara, the heads of a family that uproot its New York life to follow Rory’s dreams to the U.K. No one does surface charm better than Law, and as the film goes on, both Allison and the audience begin to discover how dishonest Rory has been about their fortunes. It never stops him from spinning new promises or possibilities — and his desperation is what truly haunts the story.

Playing the rich and charming Dickie Greenleaf in his first collaboration with Minghella, it’s understandable why Tom Ripley (Matt Damon) is awestruck. But Law makes the character more than just a louche playboy, showing his genuine affection for his girlfriend Marge (Gwyneth Paltrow) and glimpses into a more complicated man under his (admittedly very appealing) surface. It earned Law his first Oscar nomination — his second would come from reteaming with Minghella on 2004’s “Cold Mountain” —
and proved the buzz around the rising star had been warranted.  

Those who look down on romantic comedies as somehow a lesser genre be damned. Nancy Meyers’ “The Holiday” features Law at his very best in full movie star mode but also down-to-earth and relatable as Graham, a widowed father who hooks up with the woman vacationing in his sister’s house (an excellent Cameron Diaz). Law had resisted doing an all-out rom-com (the closest he came was “Alfie” in 2004), but after two Oscar nominations and some ambitious but flawed projects (“Sky Captain and the World of Tomorrow,” “All the King’s Men”), the actor signed on for this unabashedlly frothy and romantic film. It was a role that intimidated him because he wasn’t hiding behind an accent or a character look, but he pulls it off flawlessly, and his chemistry with Diaz is undeniable. Graham’s declaration of love ranks up there with the best grand gestures.  Law makes it looks easy, but the genre is one of the hardest to do well, and he’s a large reason the film has become a new holiday classic.