Which high school expelled Frank Sinatra after 47 days for general rowdiness?

A. J. Demarest High School expelled Frank Sinatra after he had attended for only 47 days because of what was described as “general rowdiness.” The school is now known as Hoboken High School.

Sinatra attended the school in Hoboken, New Jersey, beginning in 1931. He was already interested in entertainment and arranged bands for school dances, but he did not graduate. The expulsion became one of the early disruptions in a restless youth before he established himself as a professional singer.

A common mix-up concerns David E. Rue Jr. High School, which Sinatra attended before Demarest. Another distractor, Drake Business School, came later: his mother enrolled him there, hoping he would acquire practical office skills, but he left after about 11 months.

After leaving school, Sinatra worked a series of jobs, including as a newspaper delivery boy and a shipyard riveter, while pursuing singing in local clubs and on radio. His early education therefore ended long before his major breakthroughs with Harry James and Tommy Dorsey in the late 1930s.