Born in West Plains, Missouri, Jan was the eighth of eleven children of an impoverished farm couple. Her humble roots include attending a one-room schoolhouse wearing the homemade, feed sack clothes of a rural Depression-era child.
Married at age fifteen, Jan had three sons before she turned twenty. After two divorces, she headed to Los Angeles in 1955 and took on jobs as a waitress and a secretary. A chance meeting with aspiring songwriter Harlan Howard resulted in a Las Vegas wedding just one month later. One evening while Jan was washing dishes, Harlan came in the room unexpectedly and heard her singing for the very first time.
Harlan coaxed Jan to make a demo tape of his song "Mommy For A Day" which went on to become a hit for Kitty Wells. Jan later sang demos for other artists like Tex Ritter, Johnny Bond, Ned Miller, and Buck Owens. She also recorded the original demo of the Patsy Cline classic, "I Fall To Pieces". Backed by Wynn Stewart's band, Jan released Harlan's "Pick Me Up On Your Way Down" in 1959. She subsequently recorded several duets with Wynn including "Yankee Go Home" and "Wrong Company".