"The Lonesome Road" is a 1927 song with music by Nathaniel Shilkret and lyrics by Gene Austin, written in the style of an African American folk song. Dorothy Scarborough printed a melody and two verses in her 1925 book On the Trail of Negro Folk-Songs, taken down from Charles Galoway, a black road worker in Virginia; she could not date the song. Harold L. Walters later included an arrangement in his Rubank band book.
The first recording was made on 16 September 1927 by Gene Austin, with Shilkret directing the Victor Orchestra. The record was a hit and charted for Austin, Bing Crosby, Ted Lewis and Shilkret. The song has been recorded in jazz, gospel, blues, big band and dance styles. Notable versions include those by Frank Sinatra, Louis Armstrong, Sister Rosetta Tharpe, the Boswell Sisters (1934), Bing Crosby (1938), Stevie Wonder, Sam Cooke and Willie Nelson. It replaced "Ol' Man River" in the finale of the 1929 part-talkie Show Boat, sung by Jules Bledsoe. It was also used in the films Submarine Command (1951) and Cha-Cha-Cha Boom! (1956), and Bob Dylan borrowed its melody and a few lines for "Sugar Baby" on Love & Theft (2001).