Listeners are in no short supply of officially released Bob Dylan material. Between The Bootleg Series, studio albums and live efforts, there is enough to sink your teeth into as a passing fan for decades to come. But for those whose interest in Dylan goes beyond what we can hear, whose writings of it are what pay the bills, it’s a wise move to look that little bit deeper. A lift of the mighty studio album-shaped rock to see people like Eric Clapton, George Harrison, and Ringo Starr in the mix. Live shows, too, are in plentiful supply. Knowing where to start is an overwhelming ordeal, but these nine bootlegs are excellent places to begin listening to Dylan’s extra materials. They may not be officially released, but there is much to learn about Dylan as a performer and as a writer in listening to these shows, each of which is truly fantastic.
Cleveland, 1996 with Roger McGuinn
A very high bar for bootlegs from this year is set, not just because of the incredible Rainy Day Woman #12 & 35 show closer, but because the crowd becomes part of the atmosphere. The hidden instrument, should a performer know how to use it. Dylan does. That is clear from his performances of Silvio and Maggie’s Farm. Wondering where to start with Dylan’s 1990s live stage output? Here. It has a little bit of everything, from Grateful Dead covers to special guests. Both were frequent occurrences in the ‘90s, as were the rocked-out adaptations Dylan and the Bucky Baxter and Tony Garnier-featuring lineup makes here. It does not get much better than this, and it’s hard not to feel like you’re right in the mix of the audience with this recording.
Read our full review of the Cleveland 1996 show here.
Scarlet Town: Volume One
Flickers of the Rough and Rowdy Ways appeal can be heard throughout. The smooth rumble of percussion and bass slowly engulfs the track. Piano work feels soft and subtle but still a defiant momentum is found within the track. A tremendous powerhouse of a tour and a setlist riddled with hits. Dylan is not in the business of traipsing down memory lane but he does so here, with purpose for the future and a failure to look back. Brilliant slices of his discography were brought to the stage and fundamentally changed, much to the delight of those in attendance. It Takes a Lot to Laugh, It Takes a Train to Cry marks a wonderful penultimate track for this bootleg and summarises the point of The Never Ending Tour 2018 nicely. You can listen to Scarlet Town through this link.
Read our full review of Scarlet Town: Volume One here.
Expecting Rain: Volume Two
Expecting Rain: Volume Two, is an understanding of Dylan not as a writer who hit a slump but as an artist struggling to compose a new instrumental step. His lyrical choices rarely wavered in this period and despite a sense of self-doubt, there are some roaring, brilliant performances. Compilation closer Dark Eyes, has Dylan collaborate with the legendary Patti Smith. Simply phenomenal, each live version here can be called one of the very best in form for Dylan. Eight-minute renditions of It’s All Over Now, Baby Blue aside, what becomes very clear from these recordings is Dylan’s rebirth as an artist with a contemporary edge. He was no longer shuffling the deck with predictable tone or tempo, but roaring through as an artist willing to challenge his material. You can listen to Expecting Rain: Volume Two through this link.
Read our full review of Expecting Rain: Volume Two here.
1999 European Tour
Not every artist can pull their oldest works to a spot of relevancy once more, yet Dylan does it with such style. Tremendous instrumental work is the best route for overhauling those sounds and the band backing Dylan here is in constant, near-perfect form. Persuasive guitar work, fundamentally strong percussion and the steady foundation made here allow Dylan to take those subtle risks with materials old and new. Where 1999 European Tour may be a compilation of his classics, there are still a few surprises within, the Time Out of Mind tracks featured throughout are an honest and welcome experience which provides ballast to those old-school riffs. Dylan has walked a fine line between nostalgia bait and revolutionary takes on his old tunes – and what occurs throughout this compilation is nothing short of magic.
Read our full review of the European Tour 1999 here.
Rise Again
Staggering. Even with a few spots of audience discomfort, the ingenuity and desire to reinvent these songs can be heard, and it is a welcome change. An artist who does not adapt their work is an artist merely posing as a former image. Dylan was never about that – still isn’t as he tours the Rough and Rowdy Ways shows well into this year, and likely the next. Rise Again is a monumental example of his desire to keep shifting the furniture of his live performances, to maintain a new and refreshing route through. Compare this with the previous decade of performances and what shines through is an optimism, a spirited rekindling of what he loves most about making and performing music. It is a far stretch away from his semi-retirement, and that much is clear. Rise Again charts a course through 1980, a letdown in the studio, but an occasion of sincere celebration on stage. You can listen to Rise Again through this link.
Read our full review of Rise Again here.
Your Charms Have Broken Many a Heart
Prolific, perfect, and often providing a new route through the familiar tones of Dylan’s very best, Your Charms Have Broken Many a Heart is successful in compiling the very best of Dylan in a reformed period. His work on stage had hit a new peak, a veteran of the stage revisiting his past for his sake, as well as the audience’s. There is as much love for a Love and Theft piece like the groove-laden thrill of High Water (For Charley Patton) as there is for Mr. Tambourine Man. An enthused audience can often be heard, but the relatively consistent quality of the tapes means the focus is more on the interplay between Dylan and seasoned stage musicians than it is on the whoops and hollers of an audience not expecting a performance of Sugar Baby. This is the thrill kept alive by this compilation, a chance to hear the shock comes from the performance itself, not just the immediate realisation of this hit or that.
Read our full review of Your Charms Have Broken Many a Heart here.
Shining at The Beacon
Shining at The Beacon is a two-hour masterclass. Some of the most fun you can have with a bootleg recording. Take hold of those extra performances, too. Dylan covering the Rubber Soul classic is as thrilling as it gets. A boisterous performance where the band kicks into life once more, the groovy, croakier tones of Dylan fitting the song nicely. It adds a rugged edge to a song which, at its core, is a song about finding your place in the world. A nice comparison to Dylan made there, not as clear to the songwriter at the time but certainly telling of what he would try in the years after this performance. Shining at the Beacon hears Dylan get comfortable with his instrumental stylings, accept the form of his earlier works, and kick on with a roaring energy. It is a welcome step-up in quality from the usual rocking ways, and remains one of the best bootlegs available.
Read our full review of Shining at The Beacon here.
Back in the Rain
Doom and gloom may dominate the latter half of The Rolling Thunder Revue tour, but the lighter flourishes, that big band feel and the beat of optimism feature throughout. You’re Gonna Make Me Lonesome When You Go is extraordinarily upbeat, a sweet contrast to the usual heartbreak. Pair it with You’re a Big Girl Now and the beauty of The Rolling Thunder Revue is found. A contrast is made. Soft-spoken wordplay filtered by a harsh and boisterous instrumental crash. It is beautiful, and it is what defines Hard Rain. Quality recordings throughout Back in the Rain make this a must-listen compilation for those wanting to learn more about a legendary tour. Idiot Wind and Going, Going, Gone, from the fateful Fort Worth performance on May 16, are staggering. A five-month stretch of Dylan reinventing himself to a permanent end is what Back in the Rain offers.
Read our full review of Back in the Rain here.
Darkness at the Break of Noon
These are moments which inform the future of Dylan’s sound. There are some all-time greats in here. Simple Twist of Fate, in particular. A gorgeous rendition of an already beautiful track. Darkness at the Break of Noon is filled with gems. One of the best bootlegs around, from a period of tremendous, personal upheaval for Dylan. He is an artist who prides himself on being elusive, mysterious, but the pain is heard on the Rundown Sessions compiled on Darkness at the Break of Noon. Subtler vocals, a reliance on the instrumental depths, haunting at this point, is clear. A dip in the quality of the recording, but listenable all the same. Later recordings from this period hear out the overwhelming change. Simple Twist of Fate sounds completely rebuilt from its Blood on the Tracks origins, as does Street-Legal feature Coming from the Heart.
Read our full review of Darkness at the Break of Noon here.

I was at the Cleveland 1996 show with McGuinn. Personally, I would not recommend that show (Detroit 1994; second Boston October 1994 and Philadelphia August 1997 are my picks).