Reeves was born in Sherman, TX, and grew up in Austin after his father was elected to the Texas state legislature. In 1917, he joined the U.S. Army and was shot while serving on the front lines overseas. He was discharged in 1921 and apparently chose to become a vagabond, temporarily earning a living as a singer. He did a stint as a seaman before making his recording debut for OKeh in 1929 and began using the aforementioned monikers the next year. Through the 1930s he cut about 35 sides for various labels; they followed the Rodgers mold in their mix of freedom-of-the-road yodeling numbers, comic pieces (such as a mother-in-law joke parody of "St. James Infirmary"), and sentimental ballads, but Reeves specialized in reflective hobo-philosopher recitations that were quite distinct from Rodgers' hobo pieces. He composed virtually all of his own recorded material. His last recordings were made in 1938 for a radio-transcription company in Hollywood; they were mostly recitations and poems.

Occasionally Reeves appeared on radio in both the U.S. and Canada, doing brief stints on The Rudy Vallée Show, The National Barn Dance, and The Grand Ole Opry. Later in the '30s, he returned to his seafaring career and spent time in Japan. During World War II he entertained U.S. troops and then, because he spoke some Japanese, worked for the U.S. government in Japanese-American internment camps. Reeves died in a veterans' hospital in Long Beach, CA, in 1959. Several LP reissues in the 1970s reintroduced the almost forgotten Reeves to country collectors, and his complete studio recordings were collected on the 1994 Bear Family release Hobo's Lullaby.