Like any 80s born/90s raised straight woman, I had a hopeless crush on Leonardo DiCaprio. The day I found out we have the same birthday (November 11), my crush on that blonde, floppy-haired charmer only intensified tenfold. It just seemed to make sense: we both had blonde hair, a good sense of humor, and a deep concern for the environment ( for these same reasons, I also strongly identified with Dawn in The Baby-sitters Club). To be alive during the mega-rise of Leo DiCaprio in the mid-90s is simply indescribable to people who weren’t there. He oozed sex appeal and coolness and was constantly on the cover of all the teen mags like YM (rip!), Seventeen, Teen People (Rip!), Bop (rip!), Tiger Beat (Rip!) in addition to the more adult ones like Vanity Fair, Interview, and Entertainment Weekly. From like, 1994-1998, you simply couldn’t go to the grocery store to buy Fruity Pebbles and Mondo with your mom and not see Leo’s face staring seductively at you from the checkout line.
Leo was the Internet’s Boyfriend before the Internet was even really a mainstream thing for most of us. His meteoric rise to the A-list and a permanent residence on the bedroom walls and inside the lockers of America’s youth was organic, fueled by a particular and potent (and frankly almost nonexistent at this point) combination of charisma, self-awareness, looks, and genuine talent (Timothée Chalamet is heir apparent these days). He just had “it.” That ineffable quality that separates movie stars from regular celebrities and also manages to capture the cultural zeitgeist. Plus, he just seemed fun.
While you could call his Oscar-nominated turn in What’s Eating Gilbert Grape his breakthrough role, Leo’s true arrival as a star, heartthrob, and It Boy was Baz Luhrmann’s 1996 sex, drugs, and gun-filled William Shakespeare’s Romeo + Juliet. The titular Montague, Leo’s introduction in the film is a shot of him wearing an oversized suit, broodingly smoking a cigarette and scrawling his thoughts in a diary on a Southern California beach at sundown while Radiohead plays on the soundtrack. Those few frames not only perfectly encapsulate the essence of Romeo’s lovelorn, handsome melancholy, they also helped cement Leo’s offscreen image to the public. Luhrmann—who, frankly, has a particular talent for casting talented, semi-unknown male actors and creating lightning in a bottle performances—paints a relatable and lust-worthy portrait of a bad boy for the MTV generation. He’s James Dean by way of Beverly Hills 90210.
Offscreen, Leo was also getting a reputation around Hollywood (and New York) as a kind of bad boy; the ringleader of a group of young male actors of a certain age who were frequently competing with each other for roles. Dubbed “the Pussy Posse” for their pursuit of partying and women, Leo and his friends—which include Tobey Maguire, Lukas Haas, Jay Ferguson, Ethan Suplee, and David Blaine among others—frequented clubs, bars, premieres, and various events (especially those for Victoria’s Secret) throughout the 90s. According to Nancy Jo Sales’ legendary 1998 NY Mag piece titled, “Leo, Prince of the City,” the group was also protective of Leo, “They’re always ready to start yelling and swinging,” a paparazzo told her. Sometimes, that led to knock down drag out fights, including over Saved By the Bell and Showgirls actress Elizabeth Berkley. Fights between rival gangs over a woman? Doesn’t sound all that different than scenes from Luhrmann’s film.
Interestingly, in a 1994 interview with Interview Magazine, Leo said:
To tell you the truth, I have no idea what people think of me. The main thing I don’t want to do right now is create an image for myself. I notice that when I’m being consciously cool and I talk slower and wink or give a little smirk, people seem to like me more, and I think that’s how you get phony attitudes about things. Whenever I notice myself doing something just to please somebody else, I try to stop it.
Leo may not have been trying to create an image of himself, but his roles, especially from this period of his career certainly created an indelible one that has stayed etched in people’s minds (especially mine). I like to call this twinkle-in-the-eye, self-aware, mostly good-natured, charm infused with real depth, golden boy version of the beloved actor, Fun Leo.
To be clear, Fun Leo is not necessarily fully the “bad boy” Nancy Jo Sales described in her piece, but a part of that Leo is also infused into Fun Leo. For the earlier part of his career, Leo DiCaprio did a mix of Serious and Fun Leo but mostly Fun Leo, then it was mostly Serious Leo, and now I think he’s starting to do a little mix again. Fun Leo is who I’m always hoping to see onscreen, because I think it’s the best of who he is and what makes him so enjoyable to watch. Some directors have been super successful at utilizing Fun Leo correctly (Spielberg, Cameron, Luhrmann), some with mixed results (Scorsese, Boyle, Tarantino, McKay), and some (Nolan, Eastwood, Iñárritu) didn’t even bother trying to coax it out—mostly that’s because he simply couldn’t co-exist with Serious Leo in those projects.
Here’s a (non-exhaustive) list of who/what Fun Leo is:
William Shakespeare’s Romeo + Juliet (despite its Seriousness)
The Quick and the Dead
Titanic but specifically when he’s waiting at the clock and says to Rose, “so you wanna go to a REAL party?”
parts of The Beach
Catch Me If You Can (which is perhaps the most successful fusing of Fun and Serious Leo I’ve seen so far)
The Man in the Iron Mask
His scenes with Cate Blanchett in The Aviator
Most of Wolf of Wall Street but especially the “I’m not fuckin’ leavin” speech and when he’s on Quaaludes (I’d put WoWS at no. 2 in terms of fusing Fun and Serious Leo)
When he made a funny face at the Golden Globes as Lady Gaga walked past him
Most of Once Upon a Time in Hollywood
Leo is not the first—nor will he be the last—It Boy to pushback against his Fun alter ego onscreen in favor of Serious Oscar bait. But what so many It Boys fail to realize is that when you leave no room for Fun, you lose a key element in what makes you an electric onscreen presence. The presence of Fun also means there’s an element of unpredictability which draws the audience in. Daniel Day-Lewis is actually one of the best at allowing room for Fun in his very Serious performances. You can argue whether some of his films themselves are Fun, but Daniel Plainview? That’s a Fun, bananas performance in a Serious movie. Bill the Butcher in Gangs of New York (one of Scorsese’s less successful attempts at coaxing Fun Leo out) is Fun! A terror, but Fun! Leo has done more than enough to cement himself as one of the best of his generation (including for his tireless environmental activism), but he seems hesitant to fully commit again to Fun Leo for a few projects (a quick scan of his upcoming projects on IMDb shows him playing Jim Jones and Teddy Roosevelt…lmao c’mon man!!!!).
Oh how I wish he would.
Maybe Once Upon a Time in Hollywood and Gatsby will be the closest we ever get to him exploring his own stardom and offscreen reputation in some way, but I think Leo has enough self-awareness that I can hope some director (preferably a woman since he’s worked with literally only two of them) will entice him into a project that finally fully fuses Fun and Serious Leo together into something truly transcendent and revelatory. For now, I’ll take what I can get.
At least we’ll always have November 11th.
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