Whitter was born near Fries, Grayson County, Virginia, United States.[1] He learned to play the guitar from an early age, and later on, the fiddle, banjo, harmonica and piano. His love of music made him dream of a career as an artist and he spent much time listening to cylinder recordings of Uncle Josh. He found work in a cotton mill called "Fries Washington Mill", but through the years from 1923 to 1926, he frequently took time off to record. He claimed that his first session was in March 1923 in New York City for Okeh Records,[1] which would have made him the first truly country singer to record, a few months before Fiddlin' John Carson. However, this claim is not supported by the Okeh files. What is certain is that Whitter did record for Okeh from December 1923 to 1926.[1]
In his first session, he recorded nine songs, including "Wreck On the Southern Old 97" coupled with "Lonesome Road Blues".[1] The recording was released in January 1924, and was quite successful.[1] The light opera singer and country musicianVernon Dalhart heard "Wreck On the Southern Old 97" and decided to record it.[1] (That particular recording coupled with "The Prisoner's Song", went on to become the first million-selling record in country music in 1924.)[3] Other songs in Whitter's repertoire would become standards, such as "The New River Train" and "Put My Little Shoes Away". He was the first to record the harmonica tunes "Lost John" and "Fox Chase".[4] He also recorded cover versions of hits by other performer's such as Uncle Dave Macon's "Keep My Skillet Good And Greasy" and Kelly Harrell's "I Wish I Was Single Again". Although a limited musician, he supplied what record-buyers wanted and sold well. However, by 1926 there were more skilled musicians in the market, which may explain why Okeh ceased to record Whitter.