When is the closest Leo will get to an Oscar?

When he takes out the trash

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Trash Jokes More Trash Jokes

What's the difference between a homeless man and a trash can?

One of them gets taken in every once in a while.

What do you call a homeless man who trashes food you give him then says he only accepts cash?

A rootabaga.

Oscar Jokes More Oscar Jokes

What did Matthew McConaughey say to DiCaprio about his chances of winning the Oscars this year?

It's a fugazi.

What do you put in an actor's drink... OC to raise the level of anticipation at the Oscars?

Expectorant(/spoiler)

Leo Jokes More Leo Jokes

What is the difference between Chelsea and Leo di caprio?

Chelsea got Oscar. huehuehuehue.

What about Leo?

Steward: No. Leo dies.