Born in Jasper County, Illinois, Ives is probably best remembered for his music. Carl Sandburg described him as "the mightiest ballad singer born in any century". He dropped out of college to travel about as an itinerant singer during the early 1930s, earning his way by doing odd jobs and playing his banjo. He was jailed in Mona, Utah for singing "Foggy Foggy Dew", which the authorities decided was a bawdy song.
In 1940 Ives began his own radio show, called The Wayfaring Stranger after one of his popular ballads. The show was very popular, and in 1946 Ives was cast as a singing cowboy in the movie Smoky. His first book, The Wayfaring Stranger, was published in 1948.
In the 1940s he popularized several very old folk songs, such as "Lavender Blue" (his first hit, a folk song from the 17th century), "Foggy Foggy Dew" (a colonial American tune), "Blue-Tailed Fly" (an old Civil War tune) and "Big Rock Candy Mountain" (an old hobo ditty).
Ives's reputation was tarnished in the eyes of some when he cooperated with the House Unamerican Activities Committee, and named fellow folk singer Pete Seeger and others as possible communists. His cooperation with the HUAC ended his blacklisting, and allowing him to continue with his movie acting.
In the 1960s he began singing country music. In 1962 he released three major hits, "A Little Bitty Tear", "Call Me Mr In-Between" and "Funny Way of Laughing", all three of which crossed over and topped the pop charts as well.