While residing in New York, Rich performed in Fiddler On The Roof, Little Mary Sunshine, My Fair Lady, The H.M.S. Pinnafore and The music Man. He made his Pennsylvania acting debut in Ephrata ACT’s, The Music Man, as con man Harold Hill. He has also played the Villain in several melodramas, Egad What A Cad, Stop That Villain, and Dirty Work Afoot.

"No one sold a song like Francis Albert Sinatra," a music critic once wrote. Frank Sinatra was considered by many critics to be the preeminent singer of the **th century.

"No one Sells Sinatra like Rich DeSimone." Sinatra put his stamp on dozens of tunes familiar to the music lover’s ear, including the timeless theme of the Big Apple, New York, New York, and classics like Night and Day, Witchcraft, Love and Marriage, Strangers in the Night, September of My Years, The Lady Is a Tramp and My Way.

Rich DeSimone includes these favorites along with countless others in his program, maintaining the attitude and style so familiar to Sinatra fans. DeSimone follows Sinatra’s passion for detail - like wearing his hat at an angle, imitating hand gestures and Sinatra attitude, and copying hairstyle and dress. Critics raved that Sinatra was one of the first to care about the words he was singing, "reading" the lyrics with a clarity that had never been matched, wringing emotion from each line. "What is the point of singing wonderful lyrics if the audience can’t understand what is being said or heard?" Sinatra once said. DeSimone agrees with this sentiment and does an outstanding job representing "The Chairman of the Board."