| 1 | A Hard Rain’s a-Gonna Fall | prophets |
| 2 | All Along the Watchtower | playing cards |
| 3 | Baby, Let Me Follow You Down | asking, begging & pleading |
| 4 | Ballad of a Thin Man | Jones & Joneses |
| 5 | Black Diamond Bay | journalism & the news |
| 6 | Blind Willie McTell | tribute songs |
| 7 | Bob Dylan’s 115th Dream | tall tales |
| 8 | Copper Kettle | taxation |
| 9 | Crossing the Rubicon | Roman Empire |
| 10 | Days of 49 | 19th century life |
| 11 | Desolation Row | roads & streets |
| 12 | Drifter’s Escape | escape |
| 13 | Everything Is Broken | impermanence |
| 14 | Forever Young | immortality & longevity |
| 15 | Highway 61 Revisited | arresting opening lines |
| 16 | Hurricane | murder |
| 17 | I Contain Multitudes | using your imagination |
| 18 | I Dreamed I Saw St. Augustine | philosophers |
| 19 | I Threw It All Away | losers |
| 20 | Idiot Wind | cruel songs |
| 21 | If You See Her, Say Hello | missing someone |
| 22 | It Ain’t Me Babe | mistaken identity |
| 23 | Jim Jones | Australia |
| 24 | Just Like a Woman | stiff upper lip |
| 25 | Knockin’ on Heaven’s Door | afterlife |
| 26 | Lay Lady Lay | staying |
| 27 | Like a Rolling Stone | effects of fame |
| 28 | Lily, Rosemary and the Jack of Hearts | treachery & betrayal |
| 29 | Love Sick | anti-love songs |
| 30 | Maggie’s Farm | finishing |
| 31 | Masters of War | being scared |
| 32 | Most Likely You Go Your Way (And I’ll Go Mine) | separation |
| 33 | One More Cup of Coffee | coffee |
| 34 | One of Us Must Know (Sooner or Later) | misunderstanding |
| 35 | Only a Pawn in Their Game | shooting |
| 36 | Open the Door Homer (with the Band) | doors |
| 37 | Political World | chaos |
| 38 | Positively 4th Street | hatchet jobs |
| 39 | Sara | named after women |
| 40 | Seven Curses | numbers |
| 41 | Shelter from the Storm | welcoming |
| 42 | Subterranean Homesick Blues | non sequiturs |
| 43 | Talkin’ World War III Blues | normality & abnormality |
| 44 | Tangled Up in Blue | fresh starts |
| 45 | The Lonesome Death of Hattie Carroll | villains |
| 46 | The Times They Are A-Changin’ | 3/4 time signature |
| 47 | Tomorrow Is a Long Time | tomorrow |
| 48 | Tryin’ to Get to Heaven | heaven & hell |
| 49 | Visions of Johanna | strange & surreal |
| 50 | When the Deal Goes Down | impressive videos |