When Louis Armstrong was five years old, he remembered peeking through a window at Funky Butt Hall on Perdido Street in New Orleans to listen to a cornet player. “He blew so hard,” Armstrong said, “that I used to wonder if I would ever have enough lung power to fill one of those cornets.”

The year was 1905 and the cornet player that young Louis was so in awe of was Charles “Buddy” Bolden. Bolden was born in New Orleans in 1877 and was the most popular musician in the city between 1900 and ...