Sherwin was one of the original performers involved with the Epic Rap Battles of History YouTube series. As of January 2022, he has appeared in eleven episodes, having portrayed Albert Einstein, Emmett Brown, Sherlock Holmes, Ebenezer Scrooge, Stephen King, Wayne Gretzky, Egon Spengler, Voltaire, Walt Disney, Alexander The Great, and John Wick. Along with co-creators Peter Shukoff and Lloyd Ahlquist, Sherwin has acted in, and written for, episodes in every season of the series. In 2014, Epic Rap Battles of History won a Streamy Award for Best Writing. In 2015, the series was nominated for the same award. In 2016, the series was nominated for Streamy Awards for Best Collaboration and Best Writing.
