Novak was a writer for the short-lived WB sitcom Raising Dad. He performed on Comedy Central’s Premium Blend and on Late Night with Conan O’Brien.
Novak’s television acting career began on MTV’s Punk’d. He was the lead accomplice to Ashton Kutcher on the show’s second season in 2003, playing pranks on Hilary Duff, Rachael Leigh Cook, Usher, and Mýa.
After hearing Novak’s opening joke at a comedy club, executive producer Greg Daniels decided he “wanted to do something with him.” Novak was subsequently cast as Ryan Howard in the TV show The Office.
In addition to his television credits, Novak has appeared in the films Unaccompanied Minors, Reign Over Me, The Internship, Knocked Up and Quentin Tarantino’s Inglourious Basterds. He played composer Robert B. Sherman in Saving Mr. Banks (2013), and Alistair Smythe in The Amazing Spider-Man 2.
On April 11, 2013, Knopf announced it had signed a seven-figure, two-book deal with Novak, with the first book slated to be a fictional collection of “Woody Allen”-like stories.
On February 4, 2014 a book of 22 stories, One More Thing: Stories and Other Stories, was published and spent 6 weeks on the NYT Hardcover Fiction Bestsellers List. Novak also signed a deal with Penguin’s children’s books label and wrote the title The Book With No Pictures, which was released in September 2014.