There’s the Bob Dylan album discography, and then there’s the Bob Dylan Bootleg Series discography. If you have all of Dylan’s albums (or at least all of the albums that you are interested in) and you want to dive even deeper, the Bootleg Series is a veritable goldmine.
Of course, there are a lot of releases in the series: 15 to be exact (the first release was a box set which included volumes 1 through 3). And some of them have varying lengths, depending on if you want the standard or deluxe versions. Some of these collections are just for the most hardcore collectors – if you want to dive into Dylan’s weak ‘80s era, or his demos that he sent to a publishing company, go for it! If you want to listen to more than 20 takes of “Like A Rolling Stone,” well, you can do that, too.
There’s cool tracks to be found on every one of these, but we ranked them based on how well they play as standalone collections.
15) Vol. 16: Springtime In New York
ShareWhen looking back on Bob Dylan’s career, now in its sixth decade, the ‘80s tend to be regarded as his lamest, and rightfully so. (Although joining the Traveling Wilburys in 1988 seemed to reenergize him; 1989’s ‘Oh Mercy’ is one of his best albums). But the first half of the decade is one of his weakest eras. This set includes outtakes from 'Shot of Love,' 'Infidels' and 'Empire Burlesque' – not considered classics - and tour rehearsals from the era. Part of the fun about being a Dylan fan is finding the gems, even on the bad albums. And there’s some cool stuff here. Still, this collection is only for the die-hards.
Standout tracks: “Angelina,” the rocking “Price of Love,” “Lord Protect My Child,” “Dark Eyes” and on the expanded five-disc version, “Blind Willie McTell.” The latter two rank among his (many) greatest songs.14) Vol. 10: Another Self-Portrait (1969-1971) (2013)
ShareThis volume features outtakes from 'Self Portrait' and 'New Morning' and a pair of live tracks from the era. To many fans, 1970’s 'Self Portrait' is when Bob Dylan went off the rails. Following ten albums that ranged from merely good to absolute classics, 'Self Portrait' felt like the man had run out of ideas. Rolling Stone referred to 'The Bootleg Series Vol. 10' as “one of the most important, coherent and fulfilling Bob Dylan albums ever released.” We’ll have to agree to disagree on that one.
Standout tracks: the stripped-down “Little Sadie,” “Only a Hobo,” the traditional “Bring Me A Little Water” and “Sign On The Window.”13) Vol. 7: No Direction Home: The Soundtrack (2005)
Share'No Direction Home' was the title of Martin Scorsese’s Dylan documentary, which covered his early days and goes through his legendary 1966 tour. Much of this era had been covered on previous installments of The Bootleg Series. There’s some great stuff here, but this feels a bit more forced than the other installments. If not for the doc, this collection would not have been a Bootleg Series installment.
Standout tracks: “When I Got Troubles,” recorded in 1959, and a cover of “This Land Is Your Land” recorded live in New York City in 1961. There’s also a furious live version of “Masters Of War,” recorded live in New York in 1963 and a not-very-folky “Maggie’s Farm” recorded live at the Newport Folk Festival in 1965.12) Vol. 13: Trouble No More 1979–1981 (2017)
ShareThis collects mostly live performances (with some outtakes and demos) from Dylan’s Christian period. It was controversial at the time, as Dylan would preach from the stage, and he refused to play his old songs. Still, he had some gems during this era. And if you’re a fan of his gospel songs, you might rank this one a bit higher.
Standout tracks: “When You Gonna Wake Up?,” “Pressing On,” “Dead Man, Dead Man” and “The Groom’s Still Waiting At The Altar.”11) Vol. 9: The Witmark Demos: 1962–1964 (2010)
ShareIt’s literally a collection of demos that Dylan made for his first two publishing companies before he was signed. A few of these had been released on previous Bootleg installments. It’s something worth hearing for historical reasons: it’s interesting to hear Dylan before he was a cultural icon.
Standout tracks: “Hard Times In A New York Town,” “Standing On The Highway,” “Long Time Gone,” “Walkin’ Down The Line,” and the rollicking “Baby, I’m In The Mood For You.”10) Vol. 15: Travelin’ Thru, 1967–1969 (2019)
ShareThis covers Dylan’s “country” era when he released 'John Wesley Harding' and 'Nashville Skyline.' The latter, of course, featured Dylan’s duet with Johnny Cash, “Girl From the North Country.” Back then, this was a bit radical: there was not a lot of crossover between rock and country. The best parts of this collection are the many collaborations between Dylan and Cash, and some of the best parts are hearing the two icons bantering. It’s fun to listen to, but it isn’t essential.
Standout tracks: the Dylan/Cash collaborations on “I Still Miss Someone,” “Matchbox,” and “Wanted Man,” as well as Dylan and Earl Scruggs’ “East Virginia Blues.”9) Vol. 11: The Basement Tapes Complete / The Basement Tapes Raw (2014)
Share1975’s 'The Basement Tapes' was the first time Dylan (or his team) really went through his archives to issue previously unreleased material, although many of the sessions had been bootlegged. In fact, those illicit releases most likely mark the beginning of rock’s bootleg industry. These sessions were recorded by Bob Dylan and the musicians who would become the Band in 1967 at the house nicknamed “Big Pink” right outside of Woodstock, New York. This was an era where Dylan was starting to strip back his electric sound: it was less about arena rock and more about Americana. Some fans love this era, and it’s hard to deny its charm. But if you have the original 'Basement Tapes' collection, it’s not essential.
Standout tracks: “I’m Not There,” “I Shall Be Released - take 2,” “Folsom Prison Blues,” “Don’t Ya Tell Henry.”8) Vol. 17: Fragments – The Time Out Of Mind Sessions (1996-1997) (2023)
ShareBob Dylan’s 1997 album 'Time Out Of Mind' marked a creative rebirth for him. It followed two albums of solo acoustic folk covers (1992’s 'Good As I Been To You' and 1993’s 'World Gone Wrong'), and, before that, a disappointing guest-star-packed album (1990’s 'Under The Red Sky'). Was Dylan’s tank finally empty? 'Time Out Of Mind' answered that question with a resounding “hell, no.” 'Time Out Of Mind' was a critical and commercial success: it was certified platinum, topped several critics’ polls and won the Grammy for Album of the Year. So it was strange to hear Dylan in later interviews saying that he was unhappy with Daniel Lanois’ production. And while we think the album, as it was released, was great, Dylan’s other versions of the songs on this collection are amazing and are worth repeated listenings. The expanded version also has live versions of the songs. Even though many of them come from bootlegs (apparently Dylan wasn’t recording his shows in the ‘90s), they sound great and make it worth the extra money.
Standout tracks: There are so many, but all of the live tracks on disc 4 of the expanded version are great. As is the outtake “Dreamin’ Of You” and the different versions of “Mississippi,” a song that didn’t make the album. Dylan and Lanois couldn’t agree on an arrangement, and he eventually gave it to Sheryl Crow for her 1998 album The Globe Sessions. He recorded it for his subsequent 2001 “Love and Theft” album, which he produced himself (which he has done for every album since).7) Vol. 8: Tell Tale Signs: Rare and Unreleased 1989–2006 (2008)
ShareThis collection covers some of the same ground, and has some of the same tracks, as Vol. 17, including “Dreamin’ Of You” and two versions of “Mississippi.” But it has a couple of cool outtakes of from Dylan’s other Daniel Lanois-produced classic, 1989’s 'Oh Mercy' as well as stuff from 2001’s 'Love and Theft.’ There are also some great live tracks from the era.
Standout tracks: The acoustic “Most Of The Time,” the alternate version of “Someday Baby,” “Tell Ol’ Bill,” an alternate “Born In Time” from the 'Oh Mercy' sessions (he later recorded an inferior version for 'Under The Red Sky'), “High Water (For Charley Patton)(live)” and “Cocaine Blues (live).” And “Ring Them Bells (live)” from a New York City club show in 1993; hopefully, Dylan’s team will consider releasing the whole show.6) Vol. 14: More Blood, More Tracks (2018)
Share1975’s 'Blood On The Tracks' is an album whose stature just seems to grow. In 2020, when Rolling Stone updated their list of the 500 greatest albums ever, 'Blood On The Tracks' was ranked at #9, higher than any other Dylan album. And ever since the Bootleg Series was launched in the ‘90s, Dylan fans have wanted to hear outtakes from these sessions. The six disc version might be a bit much for some fans, but the single-disc sampler gives different versions of eight of the ten songs, and adds outtakes “Up To Me” and “Call Letter Blues.”
Standout tracks: “Tangled Up In Blue - take 3, remake 3,” “Up To Me - take 1,” “You’re Gonna Make Me Lonesome When You Go - take 5.”5) Vol. 12: The Best of the Cutting Edge 1965–1966 (2015)
ShareOn one hand, this peak Dylan (at least to many fans). Vol. 12 covers 1965-1966, the era when he recorded 'Bringing It All Back Home,' 'Highway 61 Revisited' and 'Blonde on Blonde.' On the other hand, well, you might just want to stick with the two-disc version. Unless the idea of one disc with twenty versions of “Like A Rolling Stone” appeals to you. Still, it’s amazing to hear different takes on songs that made up three of the most important and greatest rock albums ever.
Standout tracks: “Love Minus Zero/No Limit - take 2, acoustic,” “Just Like A Woman - Take 4, alternate take,” “If You Gotta Go, Go Now - take 2, alternate take,” “It Takes A Lot To Laugh, It Takes A Train To Cry - take 8, alternate take,” “Positively 4th Street - take 5, alternate take,” “Pledging My Time - take 1.”4) Vol. 6: Live 1964, Concert at Philharmonic Hall (2004)
ShareThis show captures Dylan at the end of an era: he is still performing as a solo acoustic act (minus a few songs where he was joined by Joan Baez) but he’s just a few months away from reinventing himself as a black leather jacket-clad rocker. This show featured not only his political songs, but some of his funniest ones.
Standout tracks: “Spanish Harlem Incident,” “Talkin’ John Birch Paranoid Blues,” “I Don’t Believe You (She Acts Like We Never Have Met),” “Talkin’ World War III Blues,” a rather fun “Mama, You Been On My Mind” with Joan Baez, “With God On Our Side” with Joan Baez.3 ) Vol. 5: Live 1975, The Rolling Thunder Revue (2002)
ShareDylan put together a massive band for this tour, including some famous musicians, like Roger McGuinn from the Byrds, Joan Baez and David Bowie’s former guitarist Mick Ronson. The band also included young guitarist T-Bone Burnett and a violinist named Scarlett Rivera, among many other players. Sometimes it’s a bit of a mess but there are some great moments as well.
Standout tracks: “Tonight I’ll Be Staying Here With You,” “Isis,” “Blowin’ In The Wind” (a duet with Baez), a rocking “It Takes A Lot To Laugh, It Takes A Train To Cry” and, of course, “Hurricane.”2) Vol. 1-3: Rare & Unreleased – 1961-1991 (1991)
ShareFans’ minds were blown by this 58-track box set of material that had been available on actual bootlegs, but never commercially. There were great alternate versions of songs, songs that Dylan never released (but that he often gave to other artists), a few humorous jams and his only spoken word piece. It’s long, but Rare & Unreleased is definitely worth your time.
Standout tracks: “Hard Times In A New York Time (demo),” “Talkin’ Bear Mountain Picnic Massacre Blues,” “Talkin’ John Birch Paranoid Blues,” the spoken-word “Last Thoughts On Woody Guthrie,” a piano waltz version of “The Times They Are A’ Changin’,” Catfish” (about New York Yankees pitcher Jim “Catfish” Hunter), “Seven Days” and “Series Of Dreams.”1 ) Vol. 4: Live 1966, The “Royal Albert Hall” Concert (1998)
ShareMany of the other installments are just for Dylan fans. Live 1966, however, is an absolute classic album. It’s also an important historical document in the canon of rock and roll music. The first disc sees Dylan performing solo acoustic – which is what his fans knew and loved him for, back in ‘66. The second disc is Dylan backed by the Hawks (later known as the Band), and feels like a battle between Dylan and the audience, who felt that his new rock and roll sound and persona was a huge sellout. At one point, a heckler from the audience famously yells out, “Judas!” By the way, it wasn’t actually recorded at the Royal Albert Hall. It was recorded at the Manchester Free Trade Hall during Dylan's world tour in 1966, but early bootlegs of the show attributed the recording to the Royal Albert Hall.
Standout tracks: “It’s All Over Now, Baby Blue,” “Tell Me, Momma,” “I Don’t Believe You (She Acts Like We Never Have Met),” “Baby, Let Me Follow You Down,” “Ballad of a Thin Man” and “Like A Rolling Stone.”