Wolpe was born in Newburgh, New York. Wolpe majored in American history at George Washington University and was active in the university's theatre department. Upon graduation, Wolpe attended graduate school at the University of Minnesota to teach theatre.
Wolpe made his Broadway debut in Onward Victoria, which closed on opening night. Other Broadway appearances include Copperfield (Mr. Dick), Into the Light (Peter Vonn), and The Sound of Music (replacement for Max Dettweiler). While in a national tour of Little Shop of Horrors, Wolpe was asked to audition for The Drowsy Chaperone by producer Roy Miller, with whom he had worked at the Paper Mill Playhouse in New Jersey. Wolpe was cast as Feltzeig, a producer. Wolpe created the role of the Wizard in Wicked's original workshops in Los Angeles. Beginning July 10, 2007, he played the Wizard on Broadway. Wolpe played his final performance as the Wizard in the Broadway company on July 27, 2008 and was replaced by P.J. Benjamin. Wolpe recently reprised the role as The Wizard in the first US National Tour of Wicked, where he replaced Lee Wilkof. His run started on September 6, 2008 and ended exactly a year later. Wolpe was succeeded by Richard Kline.
In addition to Little Shop, Wolpe has appeared in National tours of A Funny Thing Happened on the Way to the Forum and South Pacific. Off-Broadway, Wolpe has appeared in Mayor (Mayor Koch), Brownstone, Company, and The Wonder Years. His regional theatre credits include The Baker's Wife (Baker), Gypsy (Herbie opposite Betty Buckley), The Tale of the Allergist's Wife (Paper Mill Playhouse), A Class Act, Radio Gals (Pasadena Playhouse), Fiddler on the Roof (Tevye in six productions), Fiorello!, and She Loves Me (Reprise! L.A.).
On television, he was a series regular on Baby Talk and You're the One. Wolpe has guest starred on more than 80 television programs including L.A. Law (on which he played a victim of Tourette's Syndrome), ER, Six Feet Under, The Golden Girls, The King of Queens, Ally McBeal, and Chappelle's Show.
In May 2012, Wolpe premiered in the role of Morty in a new off-Broadway show based on the eponymous Old Jews Telling Jokes podcast.
- Fitzgerald, TJ. A "Drowsy" Chat with Lenny Wolpe, Broadway World, September 11, 2006. Retrieved March 13, 2008.
- Kuchwara, Michael. Lenny Wolpe Is Broadway's New Wizard, Associated Press, July 3, 2007. Retrieved March 13, 2008.
- Broadway.com Staff.P.J. Benjamin Will Be Broadway's Wizard in Wicked, broadway.com July 28, 2008. Retrieved July 28, 2008.
- Richard Kline, Randy Danson Join Chandra Lee Schwartz and Donna Vivino on Wicked Tour
- Playbill biography of Wolpe