Almost Winners from 3/3

This guy was in your high school class. He monitored your dorm in college. He sits across from you at the office. He is the "Random Tool" from the musical Dork Day In The Sun

For those of you who didn't hear it in the news, "Charlie Sheen is Winning" from My Porn House, Your Porn House

If you've ever worked hard and got nothing in return, you will fall in love with the musical You Came A Long Way For Nothing, featuring the song "Go Home"