Stein was a Ferris Professor of Journalism at Princeton and has appeared as a talking head on television shows such as Real Time with Bill Maher, Late Night with Conan O'Brien, and VH1's I Love The '80s. He's interviewed celebrities for HBO, Cinemax, and Comedy Central. In addition to writing on staff for two television shows, he created an animated show for VH1 (Hey Joel) and wrote six network pilots. His 2012 book, Man Made: A Stupid Quest For Masculinity, was a bestseller, and Fox hired him to adapt it as a film script. He's currently writing for the upcoming show American Princess produced by Jenji Kohan -- best known as the creator of Showtime comedy-drama series Weeds and Netflix series Orange is the New Black.