Singleton was born in 1809. He was a native of Nashville, Tennessee. Growing up he was a slave and had been sold several times. He managed to escape each time and finally fled to Canada. He had then traveled to multiple different towns before returning after the end of the Civil War to Tennessee. Many failed efforts to create a life for African Americans in Tennessee caused him to set out for Kansas to meet up with his partner Columbus Johnson beginning in 1877. Those who decided to follow Singleton were known as exodusters. By 1879 there were approximately 50,000 blacks who fled to the Kansas area and surrounding states. 1879 had become known as the Great Exodus. Singleton had tried to lead various different organizations that would help free blacks from slavery but all of his attempts were unsuccessful. He had later died in 1892 while in St. Louis.