Bobby grew up in Eastchester, New York, where he attended Eastchester Public Schools. He was actively engaged in art but was no stranger to the stage, starring in such Eastchester Youth Council productions of Fiddler on the Roof and the Producers.

He was a regular Cast member of Saturday Night Live from 2008 until 2017, and a (relatively) functional member of society. You may remember Bobby dancing in black tights from SNL's spoof of Beyoncee's "Single Ladies", but he had prior experience dancing in Eastchester Jazz Co. in High School.