It encompasses recordings released between the years 1973 and 1991, the time period since the previous volume of the series, released in 1971. All of Dylan's studio albums from this time span are represented, with the exceptions of: Dylan, compiled by Columbia without Dylan's input; The Basement Tapes, consisting of material predating this time period; Saved; and Empire Burlesque. The track "Groom's Still Waiting at the Altar" was added to later pressings of Shot of Love after initially being released on the flipside of a single. It includes four Top 40 singles and one previously unreleased track, an outtake from the sessions for Oh Mercy, the song "Dignity" with a new backing track overdubbed and produced in the autumn of 1994 by Brendan O'Brien.
Six of its tracks had been released as singles in the United States. "Changing of the Guards" and "Jokerman" did not make the singles chart, while "Knockin' on Heaven's Door" peaked at No. 12, "Tangled Up in Blue" at No. 31, "Hurricane" at No. 33, and "Gotta Serve Somebody" at #24. The liner notes provide a more detailed track-by-track personnel listing.
In 2003, this album was released along with the other two Dylan greatest hits sets in one four-disc package, as Greatest Hits Volumes I–III.
All songs written by Bob Dylan, except where noted.
- "Tangled Up in Blue" – 5:42
- from the album Blood on the Tracks
- "Changing of the Guards" – 6:36
- from the album Street-Legal
- "The Groom's Still Waiting at the Altar" – 4:03
- "Hurricane" (Dylan, Jacques Levy) – 8:34
- from the album Desire
- "Forever Young" – 4:58
- from the album Planet Waves
- "Jokerman" – 6:16
- from the album Infidels
- "Dignity" – 5:58
- previously unreleased recording from Oh Mercy sessions
- "Silvio" (Dylan, Robert Hunter) – 3:07
- from the album Down in the Groove
- "Ring Them Bells" – 3:02
- from the album Oh Mercy
- "Gotta Serve Somebody" – 5:25
- from the album Slow Train Coming
- "Series of Dreams" – 5:53
- outtake from the sessions for the album Oh Mercy, previously released on The Bootleg Series Volumes 1-3 (Rare & Unreleased) 1961-1991
- "Brownsville Girl" (Dylan, Sam Shepard) – 11:04
- from the album Knocked Out Loaded
- "Under the Red Sky" – 4:09
- from the album Under the Red Sky
- "Knockin' on Heaven's Door" – 2:30
- from the album Pat Garrett & Billy the Kid