What gets louder if you enter it from one end, but quieter if you enter it from the other?

A howler monkey.

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Where'd he go?

And the angel said, "He's at IHOP for never-ending pancakes" and they were like, "Word."

What starts out happy but ends in tears?

Marriage

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What did the dragon say as he entered the party?

Hey, how are you *Alduin*

What do you get when you enter a cow into the Kentucky Derby?

Milk and Bookies.