With the release of the quirky new crime caper comedy Dom Hemingway, starring the ubiquitous Jude Law and the magnificent Richard E. Grant, its easy to see that Law has come a long way from his typecasted days as the petulant pretty boy in movies like Wilde (1997), in which he played the ultimate of all petulant pretty boys, the horrific Lord Alfred “Bosie” Douglas. Its easy to miss in a lot of his early work that he’s really quite versatile.

In 2004, the infamous year of Jude Law – during which he starred in six films released, and also hosted Saturday Night Live – he proved us wrong and has been proving us wrong ever since. I used to not be a Jude Law fan, but he fast became a name that I looked for when picking out my movies. So here is a list of must see Jude Law performances, including the best of his petulant pretty boy phase.

Best Jude Law Performances

 

6. The Case-Book of Sherlock Holmes: Shoscombe Old Place (1991)

Jude Law honestly does not do much in this episode of the classic Granada Sherlock Holmes series starring the inimitable Jeremy Brett. It is, however, one of his first roles when Law was just 19 years old. He plays a young man who is revealed to have been posing as a dead woman to create the impression that she is still alive. Don’t worry about it, it all makes sense in the context of the mystery. The point is that Jude makes a lovely woman and has proved it more than once. Its also worth noting that he eventually got to play a more substantial and iconic role in a Sherlock Holmes adaptation which will feature later in this list.

 

5. Midnight in the Garden of Good and Evil (1997)

Its hard to believe that Jude Law was ever less famous than John Cusack and Kevin Spacey, but in this atmospheric Clint Eastwood directed mystery, Law plays the small but important role of Billy Hanson, the lover to Spacey’s Jim Williams. Its early on in his career, so he is definitely rocking the sullen petulance and the sultry attitude. Aside from that, its really just a damn good movie with a great story that addresses some interesting issues of gender and sexuality in the deep south. Plus, you really can’t go wrong when Eastwood is behind the camera.

 

4. The Talented Mr. Ripley (1999)

While this movie is obviously about Matt Damon’s Mr. Ripley and really excellently showcases its star, the film allows Law to play a more complex and multi-dimensional version of the petulant pretty boy, Dickie Greenleaf. The film itself is delightfully homoerotic in a lot of ways, and Law’s slightly androgynous features and cheeky British manner play in perfectly to Ripley’s complicated obsession with his friend. While the character is hopelessly charming and handsome, there is an edge of cruelty that makes us side with Ripley when things come to blows. Law’s portrayal of the character is perfect for the movie in just about every way you can imagine.

 

3. eXistenZ (1999)

I know I already listed this movie among the best sci-fi movies (throughout which there happened to be a lot of Jude Law vehicles), but it’s really good enough to list again for this, and maybe again in another list the future. I promise nothing. In any case, Law really starts to stretch himself here as the script and the style of the movie are much different than anything he’d ever done before. I think that’s probably true of most people when they work with Cronenberg for the first time. Anyway, it really pushes the boundaries of the Jude Law type up to this point and puts him in a very different context than most audiences were used to seeing him. He plays a bit of a geek for the first time, a normal man who is thrown into outrageous circumstances and has to overcome his utter mundanity to survive.

 

2. Sherlock Holmes (2009)

While the Holmesian purist in me has some issues with these movies, I really can’t deny that they are entertaining as hell and that I’d see the next one in a heartbeat. The one thing I can completely get on board with, however, is Jude Law as Dr. John H. Watson. There is very little in this world that makes more complete sense than that. Gone are the days of stuffy middle-aged Englishmen sitting in their armchairs and harrumphing companionably to each other and gone is the dumbfounded and childish Watson of old. These are men of action, daring, and intelligence who together caught countless criminals over the course of a 25 year partnership. Watson is a medical doctor and army man, so clearly he’s no idiot nor is he unfamiliar with battle. Law’s Watson could hold his own and easily keep up with Holmes. I remember specifically loving the bit near the end when Watson is herding his captured criminals, kicking at the crawling thugs, shooting the ground near where they stood, and yelling for them to move it.

 

1. Sleuth (2007)

Sleuth is where I really started to see Jude Law in a different way. I happened across this movie in reference to the playwright Harold Pinter and watched it mostly for that and partly for Michael Caine. And while this movie is wonderful and among my very favorites for a number of different reasons, the real surprise came with Law’s performance as the actor Milo Tindle and Tindle’s own performance later in the film. I didn’t know until that moment that Law had more in him than what I had seen, mostly because what I had seen left me none to enthusiastic to see much of his later performances. This is what changed my mind, and considering what he’s been getting up to these days, I’m glad I came around. I would have seriously missed out.