When Leonardo DiCaprio And Romeo + Juliet Ushered In The Era Of Cool Shakespeare

Before Leonardo DiCaprio was murdered by Rose DeWitt Bukater, he was Romeo. DiCaprio's role in Baz Luhrmann's bombastic "Romeo + Juliet" marked the beginning of his superstardom, and the film itself marked the beginning of the Cool Shakespeare boom of the 1990s. Suddenly, the Bard was hot again! Studios realized that if a beautiful, beautiful man like Leonardo DiCaprio could run around shouting in iambic pentameter and waving a gun while sobbing, there was room for more Stratford-upon-Avon badassery. 

Obviously, Shakespeare film adaptations were nothing new by the 1990s. And altering the time and setting of Shakespeare's plays has been going on pretty much since the works were penned (or, uh, quilled, I guess). But the '90s saw filmmakers twisting Shakespeare into pretzel shapes in the name of making it all so cool. This week sees the release of the ho-hum "Rosaline," which seems about two decades too late to cash in the Cool Shakespeare craze. But back in the '90s, the damn kids and their big jeans couldn't get enough of Shakespeare, baby! 

"Romeo" suffered plenty of slings and arrows from critics when it blasted into multiplexes in 1996, but that didn't matter to crowds, most of which were made up of people with cartoon hearts in their eyes as they looked at Leo. The pic hauled in 46.3 million in the United States and Canada, and has secured itself a nice little legacy. Luhrmann kept (most of) Shakespeare's text, but relocated the action of the star-crossed lovers to a type of alternate universe where the world is modern but everyone still says stuff like "Forswear its sight!" Everyone looks cool as hell, everyone has a gun, and the camera never, ever sits still as Romeo and Juliet (Claire Daines, overshadowed by DiCaprio's physical perfections) fall into doomed love. And it was only the beginning. 

My kingdom for a horse

"Romeo + Juliet" was the film that broke the bank, but it was actually beaten to the Cool Shakespeare craze a year earlier, with Richard Loncraine's uber-stylish take on "Richard III," starring a deliciously wicked Ian McKellan as Richard (leading a swell cast that includes Annette Bening, Jim Broadbent, Robert Downey Jr., Kristin Scott Thomas, and Maggie Smith). McKellen, who co-wrote the adaptation with Loncraine, reconfigures the story of the mad king to a fascist Nazi Germany-like England in the 1930s. It's not nearly as sexy and cool as "Romeo," but it's bursting with the type of crazy inventiveness that more Shakespeare adapters should strive for.

A year later, Luhrmann's "Romeo + Juliet" came out swinging, blasting its guns (which have SWORD branded on their barrels) and shocking conservative parents everywhere. While "Richard III" was targeted at adult audiences, "Romeo + Juliet" was clearly aimed at the MTV generation. "Hey kids, Shakespeare is just as 'hip' and 'with it' as your favorite skateboard stars!" the film practically screams into your face. It also rules; we should all want more movies like this. Luhrmann's direction may give you a headache, but the film is so overloaded with stimulation that it begins to crack your mind in half. And while many of the actors (including DiCaprio) have no idea how to deliver lines in iambic pentameter, others (like John Leguizamo as Tybalt, and a scene-stealing Harold Perrineau as Mercutio) knock it out of the park, or The Globe Theatre, if you will. 

Nothing would ever come close to the mania of Luhrmann's flick, but not for lack of trying. 

You will never age for me, nor fade, nor die

The same year that "Romeo + Juliet" bit its thumb at everyone, Kenneth Branagh brought forth a rather innovative take on "Hamlet." Since "Romeo + Juliet" was still relatively new, Branagh didn't get the memo that Shakespeare had to be cool now, man. Instead, the filmmaker did something no other movie had done before: kept the entirety of Shakespeare's text. Even the most faithful Shakespeare adaptations trim here and there, but Branagh kept it all, resulting in a film that clocks in at over 4 hours. While not as hip as "Romeo," Branagh's experiment, which relocates the action to the 19th century, is stunning. Sweeping, swooning, and boasting a ridiculously stacked cast that includes Derek Jacobi, Julie Christie, Kate Winslet, Robin Williams, Gérard Depardieu, Jack Lemmon, Billy Crystal, Charlton Heston, Richard Attenborough, Judi Dench, John Gielgud and more, it's one of the best Shakespeare movies ever (I said it). 

But the film that further increased the '90s Shakespeare bubble was 1998's "Shakespeare in Love." Much ink has been spilled about this film, most of it negative. For one thing, it's forever associated with the Weinsteins, who reportedly used every trick in the book to earn the film a Best Picture Oscar (when most people thought "Saving Private Ryan" should've won). But here's the thing: despite its reputation, "Shakespeare in Love" is a wonderful little film. The story finds a blocked William Shakespeare (Joseph Fiennes) struggling to write his latest play, "Romeo and Ethel, the Pirate's Daughter." Eventually, our man Shakespeare falls in love with noblewoman Viola de Lesseps (Gwyneth Paltrow). Viola happens to be a Shakespeare superfan, and decides to go undercover as a man in order to star in Shakespeare's latest play, which slowly transforms into "Romeo and Juliet." It's an unapologetically romantic and charming film and a meta-feast for Shakespeare nerds.

But the era of Cool Shakespeare would truly be cemented a year later, as the Bard headed to high school. 

But mostly I hate the way I don't hate you

In 1999's "10 Things I Hate About You," screenwriters Karen McCullah and Kirsten Smith rework "The Taming of the Shrew" into a high school setting. The end result is a funny film that's also so painfully '90s you can practically smell the pogs. While you could argue it was "Clueless," with its high school take on "Jane Austen's "Emma," that really inspired "10 Things," the aroma of the Cool Shakespeare era is all over this thing. 

In place of beautiful Leonardo DiCaprio, we have beautiful Heath Ledger, playing the coolest high schooler of all time (he smokes cigarettes). Ledger is Patrick Verona (get it? Verona? Like the place?), a cool kid who is paid to date Julia Styles' Kat Stratford (get it? Stratford? Like the place?), a hardcore feminist who has no time for the high school dweebs around her. The scheme is cooked up because Kat's younger sister Bianca (Larisa Oleynik) is forbidden from dating cute guy Cameron (Joseph Gordon-Levitt) unless Kat dates first.

It's a transaction, but of course, Patrick falls in love with the tough Kat, and she falls for him, too — until she discovers the whole "he's paid to date you" scheme. Bursting with bootcut jeans and Letters to Cleo, "10 Things I Hate About You" has earned its title in the pantheon of nostalgic teen comedies. And the Shakespeare trend rolled on, all the way to Blockbuster Video. 

Hamlet in the video store

The same year "10 Things I Hate About You" was rocking the suburbs, two other Shakespeare pics arrived. One was another effort from Branagh — a rather forgettable adaptation of "A Midsummer Night's Dream." The other was far more successful, at least artistically. Julie Taymor's "Titus" took one of Shakespeare's most-loathed plays, "Titus Andronicus," and set it in a world that feels horrifying and theatrical. Gory and overloaded with strange costumes and even stranger makeup, it's one of the most interesting modern Shakespeare pics, but it barely made a dent at the time.

Besides, there were still cooler things to come. The '90s came to an end (although one could argue the '90s didn't really end until the September 11th attacks in 2001), we all managed to survive Y2K, and 2000 brought "Hamlet" back to the screen. Michael Almereyda's take on Billy Shakes' most famous play followed the "Romeo + Juliet" mold of using Shakespeare's text in a modern setting. But where "Romeo" was all over the place, Almereyda's film is far more subdued. No longer a great Dane, Hamlet is now the heir to the Denmark Corporation (ugh). Played with intense brooding by Ethan Hawke, "Hamlet" wanders about, tragic and mad about his father's murder. And hey, Julia Stiles is back! This time, she plays the doomed Ophelia, who drowns herself in the fountain of a lobby instead of a brook. 

Almereyda's is far too low-key for its own good, but its one truly memorable flourish involves Hamlet delivering the famous "To be, or not to be" soliloquy in a Blockbuster Video, presumably right before he rented a copy of "Fight Club" on VHS. 

Heaven and men and devils and basketball

As 2000 marched on, the Cool Shakespeare era had all but shuffled off to the undiscovered country, from whose bourn no traveler returns. But there were some stragglers. Branagh tried once again to get in on the action with a musical take on "Love's Labour's Lost" in 2000. A year later, director Tim Blake Nelson took "Othello" and reworked it as "O," set it in a modern-day preschool. And oh yeah, basketball was a big part of the movie, as the Othello figure (now named Odin James, played by Mekhi Phifer) is a star basketball player. Odin is accused of sexually assaulting his girlfriend Desi (Julia Styles, yet again), but all of this is a scheme being manipulated by evil high schooler classmate Hugo (Josh Hartnett). "O" is one of the darker films from this Shakespeare era, and has no room for the slick coolness of its predecessors. Which probably explains why almost no one talks about it these days. 

The case can be made that the Cool Shakespeare era finally ended in 2006, with "She's The Man," a questionable update on "Twelfth Night" starring Amanda Bynes and Channing Tatum. The comedy badly wants to be "10 Things I Hate About You," but it really, really isn't. It also barely broke even at the box office, which more or less signaled the last gasp of Cool Shakespeare. Adaptations would continue, and some would be damn good (the recent expressionist-heavy "The Tragedy of Macbeth," with Denzel Washington, is phenomenal). 

But the days of Shakespeare being cool as hell feel long gone. Probably because there's no modern-day Leonardo DiCaprio, with his dreamy bangs and questionable grasp on iambic pentameter, to revive it.