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As a Londoner living in Boston, John appeared in the short film, She's Not the One. Shortly after, he moved to New York City to study under Suzanne Esper at the William Esper Studio. After graduating, he joined The Collective, a theatre company co-founded by Amy Schumer. He was an acting member of the ensemble and performed in numerous plays written, directed, and produced by members of the company. He began acting in short films and had a recurring role on the TV series, "Inside Amy Schumer."