For my first two, I'm going to vote in both members of the Insane Clown Posse, Violent J and Shaggy 2 Dope. Don't get me wrong, I love ICP in the most ironic way possible. I'm sure they're doing something right for releasing albums for damn near 20 years, but they are a ****ing joke.
Third nomination: Fred Durst from Limp Bizkit. For one thing, he's the biggest douche on the planet. For another thing he wrote a "hit" single with the Title of "Break Things". And lyrics such as "I feel like ****/We've all felt like ****/And been treated like ****". If someone can point out a more generic song then than that, I will give you a muffin.
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