On "Saturday Night Live", Shaiman portrayed Skip St. Thomas, the accompanying pianist for The Sweeney Sisters, a singing duo played by Nora Dunn and Jan Hooks, which earned him an Emmy nomination. He began his professional relationships with Billy Crystal and Martin Short during his tenure at "Saturday Night" Live. He wrote and sang the song "Yes" for his agent's film "Finding Kraftland." He co-wrote (with partner Scott Wittman) songs for Neil Patrick Harris when Harris hosted the 63rd Tony Awards (2009) and the 61st Primetime Emmy Awards (2009), and was Emmy-nominated for musical directing and co-writing the 82nd Academy Awards (2010).