Kenny began improvising in 2009 with The Peacock Player's "Technical Difficulties". From there, he went on to perform with and eventually direct Northeastern University's troupe "NU & Improv'd". During summers, he worked for The Derryfield Repertory Theatre, where he would perform and teach improv/musical theatre, and write original musicals. He currently performs on Harold Night Top Shelf and is a member of The Boston Sketch Company. He has studied improv at IB and at the UCB Theatre in New York. Outside of comedy, Mr. Gray enjoys analog synthesizers, distortion, and attempting to cook (but mostly burning) various asian cuisines.