Greig Stewart “Chubby” Jackson was a swinging sensation in his day. A child of vaudevillians, he was raised in an enclave of actors, musicians, and performers in Freeport, Long Island against the backdrop of Prohibition and a burgeoning club scene. Exposed to music at an early age, he jumped from high school in Nassau County to playing bass in swing bands in New York City and on the road, most notably with bandleader Woody Herman.

On today’s episode we trace the life of the man with three very special guests: Freeport Village historian Regina Feeney, jazz historian Scott Yanow, and Chubby’s daughter Jaijai Jackson. And thanks to Monk Rowe and the Fillius Jazz Archive at Hamilton College, we can add in the voice of Chubby himself.

Chubby was a colleague to Louis Armstrong, Dizzy Gillespie and other jazz greats (you’ll see him near the top of the steps in A Great Day in Harlem). His career spans the height of the swing era and the rise of bop with a side trip into headlining several kiddie TV shows in Chicago and New York. Through it all the constants in his life remained the love of family, of performing, and of Freeport.

Further Research

• Chubby Jackson oral history (Fillius Jazz Archive at Hamilton College)
• Freeport History Encyclopedia (Freeport Public Library)
• Jazz Network Worldwide
• Not Just Jazz Network
• Scott Yanow, journalist and historian
• Intro music: https://homegrownstringband.com/
• Music credits from Freesound.org
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