6. Al Capone showed no mercy when he ruled over the Chicago underworld, but the mobster also had a creative side and wrote love ballads in prison.
During the Prohibition Era, Al Capone was the undisputed boss of the Chicago underworld. He bullied, intimidated and murdered his rivals to climb to the top and amass a personal fortune through the trade in illegal beer and liquor. Capone also dealt in extortion and prostitution and his reign only came to an end when he was convicted on tax evasions. However, despite being one of the most violent men in American criminal history, Capone also had a softer side. While locked away on Alcatraz island, the gangster kept busy by composing show tunes and ballads.
Capone was brought up on opera and jazz. Then, when he was an underworld boss, he hired jazz greats like Louis Armstrong to perform in his speakeasies. Clearly, he picked up a few things. According to Capone’s biographers, he could read musical scores and play several instruments, so it was only natural that he turned to music when he was jailed for 11 years. In 2009, some of Capone’s compositions were recorded for the first time. The works are mainly love songs, most likely written for Capone’s wife, Mae, who stayed loyal even when her husband was convicted – and even though he was suffering from severe syphilis, most probably the result of dalliances with the prostitutes on his books.