Waters was raised in Lutherville, Maryland. He attended Towson High School in Towson, MD. He has performed Sketch comedy in Los Angeles since 2000, and for many years was part of the comedy duo Derek & Simon with Simon Helberg. The two starred together in the web series Derek & Simon: The Show on the comedy website Super Deluxe, which they created with Comedian Bob Odenkirk. They made two short films "Derek & Simon: The Pity Card" (co-starring Zach Galifianakis and Bill Hader) and "Derek & Simon: A Bee and a Cigarette" (co-starring Casey Wilson and Emily Rutherfurd) and had a pilot deal with HBO in 2005.
Waters has appeared on television programs such as The League, Funny or Die Presents, It's Always Sunny in Philadelphia, Nick Swardson's Pretend Time, Maron, Happy Endings, Suburgatory, The Sarah Silverman Program, Santa Clarita Diet, and The Middle. He has also appeared in films such as The Brothers Solomon, Hall Pass, For Your Consideration, and This Means War. In 2003, he co-starred in the ABC series Married to the Kellys.
