Richmond grew up in Portage County, Ohio, and graduated in 1979 from James A. Garfield High School in Garrettsville, where he won the John Philip Sousa award and where his mother still lives.

He also played a key part in the creation of the Garrettsville Community Players, directing, choreographing, and lending his creative and artistic vision to many of its shows in its beginning.

[2] Richmond worked at The Second City and Child's Play Touring Theatre before he became music director for the late-night television variety show Saturday Night Live.

Richmond has also appeared as an extra on various occasions on 30 Rock, as the character Alfonso Disparioso; and, beginning in 2010, he directed five episodes: "Argus", "Plan B", "The Ballad of Kenneth Parcell", "Today You Are a Man", and "A Goon's Deed in a Weary World".

In 2008, Richmond composed the score to the film Baby Mama, which starred his wife, Tina Fey, opposite Amy Poehler.