Why did Leonardo DiCaprio laugh at the Oscar joke?

Because he finally got it

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What's the difference between Leonardo DiCaprio and Sesame Street?

Sesame Street has an Oscar.

Why did Leonardo di Caprio want Steve Harvey to host the Oscars?

He'd get it.

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What's the difference between Sesame Street and Leonardo DiCaprio?

Sesame Street has an Oscar.

What is an ear of corn's favourite Leonardo DiCaprio movie?

Inception

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Why did Leonardo Di Caprio laugh at the Oscar joke?

He finally got it!

Why didn't DiCaprio laugh at Oscar joke?

Because he didn't get it.