Lesser was born in New York City, and lives in Santa Barbara.
His earliest work dates to 1967 with "David Holzman's Diary", directed by Jim McBride.
He is best known for the opening scene with Bruce Willis in Die Hard, his featured role in Hester Street with Carol Kane, The Big Easy, Oscar with Sylvester Stallone, Shoot to Kill with Sidney Poitier, Presidio starring Sean Connery, the Japanese film "Best Wishes for Tomorrow among others.
"Lesser has worked with Bruce Willis, Ed Harris, Alan Arkin, Arnold Schwarzenegger, Matthew Broderick, Dennis Quaid, Penelope Ann Miller, and Richard Mulligan.
[3][4] In 2011, both the Wall Street Journal and The Hollywood Reporter published a front page, tongue-in-cheek open letter from Lesser to the Internet Movie Database after they refused to correct his birthdate, which they had listed as May 28, 1938, aging him considerably.