Born in Cuba in 1916, Gaillard went to sea with his dad at 12 and got stranded alone on the island of Crete and didn't make it back to the US until he was 15.
Either that or he was born June 1918 in Claiborne, Alabama!
Whatever the case, Gaillard made his first public splash in Detroit where he ran booze as a young guy during Prohibition for the notorious Purple Gang. It was at this time he developed his interest in music.
When Duke Ellington came to Detroit, Gaillard slipped backstage to meet him.
Duke told him: "I like you because you're studying music properly."
Determined to become a musical entertainer, Gaillard moved to New York City and entered the world of show business as a 'professional amateur' where he once shared a billing with young Frank Sinatra.
And that's just the beginning of his musical story.
A truly singular human being as this four part documentary from the BBC shows.
Episode 1: A Traveller's Tale
Episode 2: How High The Moon
Episode 3: My Dinner With Dizzy
Episode 4: Everything's OK in the UK
"Sing, Swing and All That Jazz"
Free audio streaming of Henry Holloway's award winning radio program