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.

In 2016 Randolph received the Writers Guild of America Award for Best Adapted Screenplay, the Critic’s Choice Award for Best Adapted Screenplay, the Empire Award for Best Screenplay, and the BAFTA Award for Best Adapted Screenplay and the Academy Award for Best Writing Adapted Screenplay for co-writing The Big Short with Adam McKay. He was additionally nominated for the Golden Globe Award for Best Screenplay. Randolph invested nearly a year adapting The Big Short; three months for an initial draft and another three months to reduce the complexity.