Phyllis Smith. Actress: Alles steht Kopf. Phyllis Smith is an American actress from Missouri who is known for playing Phyllis Vance from The Office and Sadness from Inside Out. She also acted in Alvin and the Chipmunks: Chipwrecked, The 40-Year-Old Virgin and The OA. She also works for the casting department of Curb Your Enthusiasm, Spin City and Roswell.