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 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 Memorial Library)
Jazz Network Worldwide
Not Just Jazz Network
Scott Yanow, journalist and historian
Music credits from Freesound.org
- Jazz Bass B 1.OGG by gregstermatic. License: Creative Commons 0
- Double bass Jazz loop by elzozo. License: Creative Commons 0
- Jazz loop.wav by FrankyBoomer. License: Creative Commons 0

Episode 189: Chubby Jackson and Freeport