At Brandeis, Sherwin became an Ethics Center Student Fellow (known as the Sorensen Fellowship since 2009) while interning at Ikamva Labantu in Cape Town, South Africa.

His fellow members included Andrew Slack and Seth Reibstein, founders of the Harry Potter Alliance, and Aaron Kagan.

The group was the subject of a documentary directed by Joshua Goren which screened at the November 2006 New York International Independent Film and Video Festival.

[5] Sherwin began to perform solo as MC Mr. Napkins in Boston from 2007 until giving up the name completely in 2013 in a video posted to his YouTube channel.

As of May 2024, he has appeared in eleven episodes, having portrayed Albert Einstein, Emmett Brown, Sherlock Holmes, Ebenezer Scrooge, Stephen King, Egon Spengler, Voltaire, Walt Disney, Alexander the Great, Wayne Gretzky, and John Wick.

[2] Notable guest solvers have included Mayim Bialik, Pete Holmes, Rachel Bloom, Lisa Loeb, Josh Gondelman, and Aparna Nancherla.