Bob Dylan, Gladys Bentley, and the music of Juneteenth Jamboree

Fred Bals
7 min readJun 14, 2020

“‘Fatso’ Bentley, singing about the Juneteenth Jamboree, the oldest nationally celebrated commemoration of the ending of slavery. The State of Texas made Juneteenth an official holiday in 19 and 80, and its the only state to celebrate this event.

‘The Juneteenth Jamboree, where everything is strictly free. At the Juneteenth Jamboree there’s no shirking, no one’s working… if you really want to spree, chicks galore I guarantee. Grab your duds and come with me, to the Juneteenth Jamboree.’” ~ Bob Dylan, Theme Time Radio Hour, Episode 10 — “Summer” July 5, 2006

Since that episode of Bob Dylan’s “Theme Time Radio Hour” first aired in 2006, forty-six of the 50 U.S. states and the District of Columbia have joined Texas and now recognize June 19 as either a state holiday or official day of observance. In June 2021, Congress passed a resolution establishing Juneteenth as a national holiday; President Biden signed it into law on June 17, 2021.

A Brief History of Juneteenth

On June 19th Eighteen and Sixty-Five, 2,000 Union soldiers landed at Galveston, Texas with news that the war had ended and that the enslaved were now free. General Gordon Granger read the contents of “General Order №3”:

The people of Texas are informed that, in accordance with a proclamation from the Executive of the United States, all slaves are free. This involves an absolute equality of personal rights and rights of property between former masters and slaves, and the connection heretofore existing between them becomes that between employer and hired labor.

The date was two and a half years after Emancipation. However, Emancipation had had little impact in Texas due to the small number of Union troops available to enforce it. But, with the surrender of General Lee in April of 1865, and the arrival of General Granger’s regiment in Galveston, the Union forces were finally strong enough to bring about freeing the 250,000 slaves in Texas.

Fred Bals

Corporate Storyteller. Tech enthusiast. Mini Cooper fanboy. One-time chronicler of Bob Dylan’s Theme Time Radio Hour. Husband of Peggy. Human of Lily Rose.