Randolph was born in Nashville, Tennessee. After graduating from Yale Divinity School, he worked as a cultural studies and philosophy professor at various universities in Vienna, Austria (including Webster Vienna Private University) in the 1990s.
In 1997, Randolph spent a weekend giving lectures at the University of Southern California. From a chance meeting with someone who worked for the Farrelly brothers, Randolph was inspired to attempt screenwriting.
Randolph has written screenplays for several films and TV movies including The Life of David Gale (2003), The Interpreter (2005), Love & Other Drugs (2010) and The Big Short (2015).

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