Sam Chatmon (c. 1899-1983), a celebrated singer and guitarist who spent most of his life in Hollandale, sometimes performed with his brothers in a renowned family string band billed as the Mississippi Sheiks. He embarked on a new solo career after coming out of musical retirement in the 1960s. Many local musicians have performed here on Simmons Street, known as "the Blue Front," once one of the most vibrant centers of blues activity in the Delta.
Hollandale Blues history dates back at least to the 1920s, when the Mississippi Sheiks, Sam Chatmon, Bo Chatmon (aka Bo Carter), Eugene Powell, Robert Nighthawk, and Houston Stackhouse performed at local drug stores, cafes, and other businesses, in addition to jukehouse parties and dances on nearby plantations. Most of the Mississippi Sheiks, a popular string band known for their hit recording "Sitting on Top of the World" (1930), were members of the Chatmon family, several of whom moved from their native Hinds County to the Hollandale area around 1928 and worked here as cotton farmers as well as musicians. In later years Sam Chatmon moved into town and took a job as a night watchman, while his brother Bo settled in Anguilla.
After blues enthusiasts began to seek Sam out in the 1960s, he traveled to play
concerts and festivals around the country, most often in the San Diego area, and recorded several albums including Hollandale Blues and The Mississippi Sheik. He grew a long beard, as his fiddle-playing father had done, and endeared himself to new audiences who were entertained by his risqué double-entendre songs. In 2009 the city of Hollandale purchased Chatmon's house at 818 Sherman Street to move it here to "Blue Front," an area once famed for blues, liquor, and gambling. Chatmon sang about Blue Front in his song "Hollandale Blues," but told friends he preferred less rowdy surroundings.
Author Kathy Starr, whose grandmother operated the Fair Deal café on Blue Front, wrote in The Soul of Southern Cooking: "Blue Front was a string of little cafes where everybody gathered on the weekend. It was the only place blacks had to go, to get rid of the blues after a week's hard work in the cotton fields. Everybody lived for Saturday night to go to Blue Front. ... if you wanted a half-pint or a pint of whiskey or corn liquor, you could get it at Fair Deal because Grandmama and the chief of police had an 'understanding.'... The Seabirds (Seeburg juke boxes) would be jammin' all up and down Blue Front with Howlin' Wolf, Muddy Waters, and B. B. King. Sometimes they would be there in person over at the Day and Night Café. The great
blues singer Sam Chatman [sic] came to Fair Deal often. People danced, ate, drank, and partied till the break of day. Saturday night without a fight was not known."
Among other former Hollandale area residents, Eddie "Guitar Slim" Jones went on to the greatest fame in the 1950s after moving to New Orleans. Others include bluesmen William Warren, Willie Harris, Mott Willis, J. D. Short, James Earl "Blue" Franklin, and Joseph C. Moore ("J. C. Rico"); Eugene Powell's wife Mississippi Matilda; the Buckhanna (Buchanan) Brothers string band; and soul singer Ruby Stackhouse, better known as Ruby Andrews.