Bobby was born in Harrisburg, PA. His family owned the J A Troup Music House stores in Harrisburg and Lancaster. Bobby's father played the piano and music was a big part of his young life.

After graduating from the Pennsylvania Wharton Business School, he enlisted in the Marines. When he was not called for duty right away, he went to New York and worked for Tommy Dorsey as a writer. After the incident at Pearl Harbor, Bobby was sent to Officer Training School in the Marine Corps.

When he returned from the Marine Corps. He told his mother that he wanted to try to become a song writer. He bought a 1941 Buick with his first royalty check from his song "Daddy." At that time, New York and California were the places for song writers to be.

He said he would give himself two years to make it and headed off to Los Angeles, California, writing half of the song "Route 66" in the car along the way The Lyrics.  The song was formally recorded on March 16, 1946.

His idol was Nat King Cole and when he heard Bobby's songs, he loved them. Bobby's songs have been recorded by many artists through the years, including Julie London. The song "Meaning of the Blues" was written for Julie. Along with several others.

His move into movies and TV shows was the result of studios getting actors to act as singers and musicians, and Bobby was ask to be involved since he really knew what he was doing. He played those parts in many shows, and was great at being himself at the piano.