The compilation features selections from their first five albums and two new songs, 'The Sound of Crying' and 'If You Don't Love Me', both of which were issued as singles. Three other previously released tracks - 'Life of Surprises' from Protest Songs, 'I Remember That' from From Langley Park to Memphis, and 'All the World Loves Lovers' from Jordan: The Comeback - were also released as singles to promote the compilation.
As well as the popular audio formats of the time (LP, CD and cassette), A Life of Surprises was also released on a 45-minute-long VHS video with a slightly different track listing. The video features only eleven songs and does not have the title track, 'A Life of Surprises', 'Faron Young', 'Wild Horses', 'All The World Loves Lovers', 'Goodbye Lucille #1', 'I Remember That' or 'Cruel'. However it does feature videos for 'The Golden Calf' and 'Looking for Atlantis'. This means that only nine songs are common to both audio and video releases.