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Everyone fears the Dread Pirate Roberts. It's in the name: you wouldn't fear the Friendly Pirate Roberts or the Singing Pirate Roberts.
"Besides," Inigo explains to Fezzik, "I have a terrible singing voice."
"That's by your choice," Fezzik replies and Inigo can't help but smile. That's going to be the real problem. The new Dread Pirate Roberts can't stop smiling and no one's going to fear that.
He's found his revenge. More importantly as it turns out he's found the missing half of his own heart which was standing there the whole time.
"I'll be dreadful. You can sing."
"Anything."