Al Capone: Mob Boss and… Music Lover?

By Keegan Morris |

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Al Capone

Al Capone, c. 1935

There’s a scene in the 1987 movie The Untouchables where Robert De Niro’s Al Capone is moved to tears at a performance of Leoncavallo’s Pagliacci.

Filmmakers often use opera to heighten drama, convey opulence, or underscore the onscreen action. And director Brian De Palma's scene in the heavily fictionalized Untouchables does accomplish these effects. But even still, this Capone scene does have at least some basis in fact.

Al Capone is infamous for his ruthlessness and his theatricality, which have cemented him forever in popular imagination. But believe it or not, the notorious Chicago crime boss did have an artistic side. He loved music.

Note: Clip contains violence

It started with opera. According to a biography written by his niece, Deirdre Marie Capone, young Alphonse’s introduction to the art form was listening to opera records with his grandmother. He would also tune in to operas on the radio. “Uncle Al,” the author remembers, “loved the opera; his favorite was Aida.” Music remained a key pastime and part of his family life: Capone would reportedly "joyously sing at family functions."

But he also loved jazz. As the dominant figure in Chicago’s mob scene, he had his fingers in every pie [ugh], including entertainment. Deirdre Marie Capone describes Al and his brother Ralph as the “biggest jazz impresarios in the city.” One of the outfit's favorite piano players, Jack Woodford, attests that Capone’s favorite song was “Roses of Picardy.”

"Fats" Waller, 1938

One famous episode took place in 1926, as Thomas Wright “Fats” Waller was finishing a performance in Chicago. The stride pianist’s autobiography recalls that after his show, he was approached and abducted by four mobsters. Arriving at one of Capone’s establishments and told to play, the frightened musician soon realized that he was to be the musician for the capo’s birthday party… a party that lasted at least a day, and according to some sources, up to three. Years later, Waller’s son, Maurice, shared that Fats was paid a hefty sum: $100 per song.

Fast-forward to Capone’s famed stint in Alcatraz. One way he passed the time as he was doing time was by playing music. The diminutive don is said to have begged permission to retain musical instruments and form a prison band: “The Rock Islanders.” In the band, he played banjo and mandola, letters from Capone to his son tell us. He reportedly loved writing music, and as a musician, professed to have mastered over 500 songs.

Most famously, in 2009, sheet music written in his hand — and that he claimed to have composed — sold for $65,000. But perhaps unsurprisingly, given his penchant for lawbreaking and talent for mythmaking, it was a song he adapted and wrote off as his own.


Learn more about Al Capone and his ties to Chicago in Chicago Stories: Al Capone's Bloody Business, premiering on WTTW on November 1 at 8:00 pm. For more information, visit wttw.com/chicagostories.