John Prine's 1984 album Aimless Love was his first release on his independent record label, Oh Boy Records. Prine and his long-time manager Al Bunetta formed Oh Boy Records in an attempt to take control of his own music.
Aimless Love would be Prine's first album of original material since Storm Windows in 1980. In the years leading up to the release, he had settled in Nashville co-writing songs for other artists, notably the number one country hit “Love Is On a Roll” by Don Williams. Several of Prine's collaborators from this period, like Bobby Braddock and Donnie Fritts, would receive credits on Aimless Love.