Leonardo DiCaprio Prepares for Oscar Weekend

Leonardo looked into the antique mirror in the master bathroom of his mansion. His hair was styled perfectly, his skin was flawless, and his facial hair had never looked more beautiful. But there was a sadness in his eyes, a sadness he could conceal from the rest of the world, but here alone could not hide from himself. He picked up the Waterford Crystal soap dish that Marty had given him as a wrap present and threw it at his reflection, shattering the glass. “This is a metaphor for my dreams,” he thought as he watched his assistant pick up the shards of glass with her bare hands.

Oscar Weekend was always a difficult time for Leo. If he wasn’t nominated, he had to act happy for the people who were which was hard enough, but the years he was nominated were even worse. Because try as he might, he always ended up the proverbial bridesmaid. And this year was the worst of all, because he no longer had his friend Kate to commiserate with. She had her trophy now, and because of sub-clause 46a of the Celebrity Friendship Contract they had signed on the set of Titanic, they now no longer spoke.

Leo pressed the secret button underneath the mantle of his bedroom fireplace to reveal his hidden room, where he kept all of his most treasured possessions. He bypassed the cocaine corner and went straight to antique hope chest situated beside the display case containing the eponymous mask from The Man in the Iron Mask. He opened the chest and found what he was looking for immediately: the “Kate + Leo BFFs Forever” scrapbook.

Flipping through the pages he was flooded with happy memories. The image of Kate setting fire to Jennifer Connelly’s garage after she beat her for Best Supporting Actress. The sound of Kate’s laughter as he smashed the windows of Jamie Foxx’s stretch Hummer after losing Best Actor to him three years later. The unforgettable year they had both lost and had taken a private jet to Argentina where they paid a tidy sum to hunt and kill a man a woman who bore a striking resemblance to Forest Whitaker and Helen Mirren, respectively. A single tear rolled down Leo’s face as he realized that he would never again be able to create a cherished memory of violence and mayhem with his friend.

He was pulled out of this melancholy reverie by a new text alert. His heart leapt as he saw that it was from Jonah. “hey bro, im downstairs w/ those croatian models u brought home last nite. care 2 join 4 some jacuz?” Leo dried his tears, directed his eyes to the cocaine corner, and smiled.

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Catweazle is an 11th century wizard trying to make his way through the modern world while living in a disused water tower with his pet toad.
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12 Responses to Leonardo DiCaprio Prepares for Oscar Weekend

  1. FRQ says:

    I assume this is the same hidden room where he keeps his whiskered jeans?

    (BTW, are we doing an Oscar viewing party here on Sunday?)

    • We definitely can if you guys want to! I’ll be watching them, so I can toss up a discussion post.

      • welcometocostcoiloveyou says:

        Yes, please! I usually love watching the Oscars, but this year, I’m just not that excited about it. I’m sure I won’t be able to NOT watch it, so it would be fun to chat with all of you while it’s on.

  2. collin0truckasaurus says:

    Do you think Claire Danes ribs him about how he hasn’t won an Oscar yet? They hate each other right?

  3. Sota says:

    You know that he is just desperate to win the Oscar. It was so obvious, when he showed up and did the Titanic thing with Jonah Hill on SNL. I hope he wins.

  4. flanny says:

    “This is a metaphor for my dreams” is the best.

  5. Sota says:

    I am going to make my friends sign a Celebrity Friendship Clause.

  6. Casey says:

    He must have been really upset to skip the cocaine corner like that.

  7. mordonez says:

    From Drew Magary, writing a deliciously hateful column on Deadspin:

    Leonardo DiCaprio: I’m gonna be honest: Any time I see Leonardo DiCaprio play a grownup (which happens in every movie now), I just keep waiting for him to sweep his bangs across his face and wear little boy suspenders and start defying his parents. This is my life, Mom! Jeez aloo! I bet he totally was one of those guys who got a beard transplant.

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