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).
Randolph invested more time than usual when it came to adapting The Big Short. It took approximately six months, three months to write it all down and three months to reduce the complexity. Additional time was taken to do more research and come up with ways to not confuse the audience with complex information. Overall, Randolph believed in his work and the success of the movie. His goal was to provide a lesson to the younger generations, those who didn't lose everything in the 2008 financial crisis, that fairness doesn't matter.
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 didn't win but was nominated for the Golden Globe Award for Best Screenplay.
