Stamatopoulos had written a spec script for a Simpsons episode out of love for the show, and Andy Dick convinced him to submit it to The Ben Stiller Show, which got him hired. He met and worked with Bob Odenkirk. After Stiller's show was canceled, he moved to New York City, where he wrote during the 1990s for The Dana Carvey Show, Late Night with Conan O'Brien (also with Odenkirk), Late Show with David Letterman, Mr. Show with Bob and David.