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 as a 45-minute-long VHS video with a slightly different track listing. The video featured only 11 songs and did not include 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 did feature videos for "The Golden Calf" and "Looking for Atlantis". Thus only nine songs were common to both audio and video releases.