Waters was raised in Lutherville, Maryland. Waters is dyslexic, and was in special education in school. As a child, he aspired to be a professional baseball player, but didn't make his high school team, and so became a Little League umpire. He attended Towson High School in Towson, Maryland, graduating in 1998. The following year, he went to Second City in Toronto, Canada, 1999 to study sketch and improv comedy.
