Photo: Mike Marsland (Getty Images)
With a Ph.D. in luxurious badassery, Leonardo DiCaprio is a true Hollywood prophet whose tales of million-dollar sushi, drugs unavailable to the general public, and the black market vintage toy underground would pique any man-bunned enthusiast’s interest. Leo’s expertise knows no boundaries, but for Brad Pitt‘s needs, the most valuable asset is revealing that mysterious head-in-a-box that has eluded Tyler Durden for decades, an Academy Award for Best Actor.
The two A-list celebrities have similar career trajectories, both starting in TV and small film roles leading to a never-ending cascade of love and adoration from audiences around the world. But somehow during years of partying, drugs, women, Italian vacations, and a personal support group that inspired HBO’s Entourage, Leo somehow managed to acquire the one man that proved unattainable in his past.
That man’s name is Oscar, and with Leo’s guidance, Brad may be ready to meet him. Here’s a step-by-step guide on how he can win that coveted gold statue.
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Leonardo DiCaprio Oscar Guide
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Avoid Marriage As Much As Possible
Leo has managed to remain relatively single, casually dating models and actresses. Brad already missed the mark on this one, but post-divorce Brad Pitt may be ready for adult-onset adolescence.
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Try Not To Care Too Much
Publicly, Leo has always been an enigma and somewhat aloof to winning awards. Being insanely rich and handsome is an effective coping skill for stress. Act like you don't give a shit and people will swoon.
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Practice A Cannabis-Forward Lifestyle
Whether you're puffing a pen at the Oscar's or surfing and ripping bong hits in Malibu, the lucky charm seems to be the stickiest of the icky.
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Take A Beating From The Academy
The academy will push you down, spit on your face, and kick you in the nuts; just keep crawling through the woods while a bear humps you to death. Someone will feel bad enough to award you an Oscar.
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Play A Character Who's An Asshole
Brad and Leo both excel at being the prettiest girl in the room while also somehow being a bad boy. Yell and scream as much as possible with crazy eyes until the academy gives you a statue so you'll stop.
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Date Models/Actresses Half Your Age
An Oscar worthy performance comes deep from within, but a gorgeous muse who thinks a VHS is a curable form of heartburn doesn't hurt the self confidence.
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Work With Incredible Directors Who Make You Look Good
Both actors have hefty resumes, working with basically every big director in the business. And both actors have worked with Quentin Tarantino (who is basically the over-looked/under-appreciated actor whisperer) several times.
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Stare Into The Camera Dramatically
It means you're serious, and possibly have gas. But mostly you're hungry....or horny.
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Be A Little Crazy
Not a problem: Brad married and fathered children with a woman who formerly wore a necklace containing Billy Bob Thornton's blood and is probably a vampire. Leo has a crew of close friends that are referred as "The Pussy Posse." Crazy is as crazy does.
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Ignore The Critics
Sprinkle in a few crap movies with a performance that's Razzie-worthy. Just to remind everyone that you're rubber and they're glue, but those $20 million checks better go through.
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Be On 'Growing Pains'
Both Brad and Leo waxed intellectual on the '80s hit TV series, Growing Pains. Does this mean Kirk Cameron is next to make an Oscar push? We've got our money on "Boner."
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Work With Jack Nicholson
Brad Pitt passed on Matt Damon's role in The Departed while Leo beat up guys, sold cocaine, and eventually slept with Damon's girlfriend....so, Pitt kind of worked with Nicholson by proxy.
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Long Hair, Don't Care
Feel free to never cut your ridiculous mane and rock goatees/full beards that scream to everyone how much you don't give a f@#k.
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Support A Humanitarian Effort
Brad's humanitarian efforts have helped rebuild New Orleans post-Hurricane Katrina, and with the the help of his ex-wife, Angelina Jolie, have funded conservation and environmental organizations all over the world.
Leo has his own organization that is essentially trying to save the entire planet.
