It had been a while since Bob had done something truly strange or surprising. Sure, there were those solo acoustic folk albums in the nineties, but those were more of a throwback to something he hadn’t done since his debut than it was something Dylan had never really tried before. He had some bad albums, but the last really strange set of records were the Born Again trilogy from the late seventies and early eighties. One would have worried at this point that the man who went electric didn’t have any more tricks up his sleeve.

So it was heartening in 2009 when Bob announced the arrival of his album Christmas In The Heart. For most artists, a seasonal holiday release signaled a quickly recorded and cynical cash-grab, but Dylan pledged that all monies from this album would be donated to charity, so that clearly wasn’t the motivation here. Instead it must be that Bob really, really wanted to record a Christmas album. And this is very much a Christmas album. The production brings to mind a 1950s Bing Crosby record with a small mixed chorus and sleigh bells and a tasteful restrained arrangement from the touring band.

As odd as it was, it was seen as a one-off and received surprisingly warmly. Of course, it helped that Dylan’s next record, Tempest, was a return to the originals and production style of most of Bob’s 2000s output. So, when in 2014, the Frank Sinatra tribute album, Shadows In The Night, was announced people were perplexed but not overly worried. They figured it would be Bob getting this out of his system before going back to business as usual.

Unlike Chirstmas In The Heart, Shadows In The Night was not produced to be reminiscent of the song’s original format. In fact, the sound is very similar to the more crooning ballads from Love & Theft or Modern Times – it was Bob’s usual touring backing band and not some big band brass section. Sure there were a few horns added here or there, but they were mostly for texture and mostly so low in the mix as to be inaudible. Again, the audience and critics embraced the record a lot more positively than one would have expected, mostly because it seemed harmless.

Rumors were at the time of recording Shadows In The Night, there was enough material left on the cutting room floor for an entire second album of Frank Sinatra covers, but no one was really hankering or demanding another album of that – so when those tracks did surface as 2015’s Fallen Angels, the reaction was a little more dismissive. Not that the album was really any worse (or different) from the last one – but everyone was a little more begrudging in indulging old man Dylan’s latest hobby.

Things really went off the rails the next year with 2016’s Triplicate. The albums titled stemmed not just from the fact that this was Bob’s third Sinatra album in a row, but because it was itself a triple album. Bob even brought out the swinging big band sounds for three or four tracks on the album, but few people made through all thirty tracks to find the handful of nuggets buried in there. Some folks were starting to get worried about Bob’s mental faculties and feared that this might be some new weird symptom of senility.

And that’s where the story ends. At least for now. There’s a new album coming out June 19th. Bob’s first collection of originals since 2012’s Tempest. That’s an even longer gap than the seven years that separated Under The Red Sky and Time Out Of Mind. Whether this is the start of the next phase of Dylan’s career, or it will just be more of the same as last week’s playlist is hard to say. Three songs have been released already, and they do feel very much of the Love & Theft through Tempest vibe, although one of these songs, Murder Most Foul is notable already for two things: At nearly seventeen minutes, it is Bob Dylan’s longest song, and it is the first #1 Billboard charting single Dylan has had in his entire career. So there are still a few surprises left up his sleeve.

In the 21st Century, Dylan had created a new way of looking at and making albums that was really working for him. Instead of trying to crank out a new record every year, he would wait 3 – 5 years until he had enough originals ready and wouldn’t have to rely on covers or co-writers. Instead of dealing a bunch of guest stars he would just use his semi-anonymous touring band. And instead of butting heads with hotshot record producers, he would just record the albums himself (albeit under the unnecessary pseudonym Jack Frost). There was no point in trying to chase trends or score another big hit. No matter how good his records were, they were only going to sell so many. And no matter how bad they were, the faithful were still going to buy them anyway. So he might as well make the records he wants in the way he wants to make them.

The first of these albums, Love & Theft, had the dubious distinction of being released on September 11th, 2001. It was a modest album and a moderate success compared to the previous record, Time Out Of Mind, but it sounded like Dylan was having fun again. Given the gap between albums and Bob’s recent health scare, critics were loathe to be too harsh on any of these records, for fear that he would die and it would be his last.

This was followed in 2006 by Modern Times, a truly ironic title as the album seemed to completely ignore the present in favor of the past… except for an odd shout-out to Alicia Keyes. The next album came out relatively quickly, just 3 years later. Together Through Life was not as well received as it felt like Bob was trodding a well-worn path by this point. Plus, the use of Robert Hunter as a a co-writer, and adding Tom Petty’s Mike Campbell and Los Lobos’s David Hidalgo to the usual musicians on the record started to smack of his Down In The Groove days. In fact, the most distinctive thing about Together Through Life (which came into being as an extension of the soundtrack to the otherwise forgettable Renee Zellweger film, My Own Love Song) was the prominence of Hidalgo’s accordion. It is utterly ubiquitous on that album.

Bob’s last album of original material appeared in 2012. It was received much more warmly than it’s predecessor, if only because there was a Xmas album that came out in-between, making everyone grateful that Bob was writing his own tunes again. However, the fact that the title of this album, Tempest, mirrors that of Shakespeare’s last play had led many to speculate (or worry) that this would be his final album of new material.

It was not his final album period, as Bob still had one more curve ball up his sleeve as we will see next week.

After squandering his first Lanois-assisted comeback, 1989’s Oh Mercy, with 1990’s Under The Red Sky, Bob was in a bit of a quandary. In 1991 he released no new album for the first time since the end of his Christian phase a decade prior. When he finally did decide to go back to the studio, he once again fell into the same bad habits that produced Knocked Out Loaded and Down In The Groove. He hired David Bromberg to produce the album, and while those two records had very few self-penned originals, Dylan decided to do a whole album of covers.

The project went well, and everyone seemed happy with the final product, but at the last minute Bob decided to throw on a hastily recorded solo acoustic track, much as he had done with The Wedding Song for Planet Waves or Dark Eyes for Empire Burlesque. So Bob threw a mic up in his garage studio and quickly knocked out 15 or so tracks to choose from. But when he listened back to the tapes, he decided to scrap the Bromberg sessions and just release the acoustic album. While the albums itself didn’t excite anyone particularly, everyone was also relieved that Dylan wasn’t embarrassing himself either. In fact, the only person who really seemed into the album, was Dylan himself; who recorded a nearly identical album of solo acoustic folk songs, World Gone Wrong, the next year. It seemed to keep him happy and busy and re-charge his batteries while waiting for the muse to strike again.

It was a type of album he hadn’t really done since his very first album before he started writing his own material in earnest. While most of Bob’s periods tend to last three or four albums (see the electric trilogy, the born again trilogy, or the Sinatra trilogy), this mid-nineties acoustic folk revival only lasted 2 albums before Bob had gotten everything he would want out of it, buying himself enough time and goodwill to record Time Out Of Mind several years later. So while putting together this playlist, I also included four track from that solo debut (House Of The Risin’ Sun, Fixin’ To Die, In My Time Of Dyin’, and Man Of Constant Sorrow) that fit together in terms of instrumentation and authorship if not chronology. I also included a version of Woody Guthrie’s Pretty Boy Floyd that Bob had recorded for a tribute album in the mid eighties, as there isn’t much between the two periods to really link them together.

Now that Bob knew how to do a record when he didn’t have the songs, he decided never to do that again. A second Lanois-assisted comeback, 1997’s Time Out Of Mind would buy Dylan both the credibility to do what he wanted next time, but also the allowance to take as much time as he needed to get to that next record.

With the increased visibility to his profile that the Wilburys project provided, Dylan knew his next solo record would need to be extra-good. Forsaking his habit of filling up an album with covers and rejected tunes from the record before it, Bob sat and wrote ten whole new songs by himself for Oh Mercy. On the advice of Bono, Dylan hired French-Canadian producer, Daniel Lanois, to give this new record a distinctive sound that was appropriate to the tunes rather than chasing the current trends.

The gambit paid off, with Oh Mercy receiving some of Dylan’s best reviews and pulling him out of his commercial slump. Unfortunately, Lanois and Dylan butting heads frequently in the studio, so far his next record, Under The Red Sky, he went back to just getting a bunch of famous friends to guest on his album. That’s why I ended up putting those tracks on last week’s playlist/blog. Under The Red Sky, while not as bad as Down In The Groove or Knocked Out Loaded, quickly killed whatever career momentum Daniel Lanois had given him.

So Bob took a few years off, writing no new material for seven years and only recording a couple of solo acoustic albums of folk covers (which we will delve into next week). By the time, Dylan finally felt inspired to write again, we swallowed his pride, bit his tongue, and hired Daniel Lanois again.

And once again it worked. Time Out Of Mind got all sorts of attention and Grammies and awards. Of course, it probably helped that Bob nearly died of a weird fungal infection in his heart right before the album came out. It was a bold marketing move, and also cast a pall of mortality that only added to the album’s mystique.

While 1989’s Oh Mercy and 1997’s Time Out Of Mind might not have been consecutive chronologically, the two fit together quite well. Lanois’s production style, a swampy, eerie soundscape, unites the two albums in theme and tone. Plus the popular conception of both of these records as something of a pair of comebacks, pairs them nicely as well.

Bob learned his lesson, and realized that if he wanted to avoid working with Daniel Lanois again (which it certainly seems he did) he was going to have to wait until he had a good album he wanted to record instead of merely pumping out product every year because it was what was expected of him.

The Eighties were not a good time for Dylan. Then again the Eighties were not a good time for most of the rock stars of the sixties and seventies. The dominance of MTV and the ubiquity of synthesizers and drum machines left these former legends feeling un-cool and out-of-touch for the first time ever, just as they were entering middle age. Some tried desperately to cling to any sort of commercial success of relevance, embarrassing themselves in the process. Others just gave up completely relegating themselves to playing their hits on the oldies circuit at state fairs and not trying to enter the cultural conversation any more.

Without the passion and fire of spreading the gospel, Dylan was at a lost as to why exactly he should continue to create new music. It had merely become a habit to him at this point, and one he wasn’t very engaged in. Bob tried his hand at hiring in-vogue producers to try and reignite the spark: Mark Knopfler for Infidels, Arthur Baker for Empire Burlesque, Don Was for Under The Red Sky. In between these albums were a couple of records that seemed to have no one at all at the helm. Knocked Out Loaded and Down In The Groove seemed to happen out of sheer inertia and not because anyone involved was really trying. While Self Portrait may have engendered outrage, hatred and confusion, these records were considered worse simply because they didn’t elicit any response at all beyond apathy.

Without a regular backing band, Bob would rely on a more popular act to support him on tour, as well as draw an audience to the show. Dylan did tours with the Grateful Dead and Tom Petty during the Eighties to try and drum up interest in his flagging career. And it wasn’t just on the live stage where Bob was relying on guest stars. During this period Bob recorded with just about everyone: Sly & Robbie, Mick Taylor, Ronnie Wood, Full Force, Stevie Ray Vaughan (and his brother Jimmie), Anton Fig, Al Kooper, T-Bone Burnett, Dave Stewart, Eric Clapton, Kip Winger, Randy Jackson, Paul Simonon, Steve Jones, The Plugz, David Crosby, Bruce Hornsby, Elton John, George Harrison, and Slash. He even co-wrote songs with Carole Bayer Sager, Sam Sheppard, Michael Bolton, and Gene Simmons during this period.

The most successful of these team-ups, came not as guest stars, but a true collaboration. The Traveling Wilburys managed to raise Bob’s profile more than any of his appearance at Live Aid or We Are The World (or the horrific film Hearts of Fire) would ever do. The super-group consisted of Roy Orbison, George Harrison, Tom Petty, and ELO’s Jeff Lynne. Freed from having to write and lead the whole album himself, Bob’s three contributions to this album really stood out.

Shortly after the first Wilburys album brought the best reviews of the decade for Dylan, he ditched the big-name backing bands and started what was jokingly titled “The Never-Ending Tour”. Playing smaller cities and smaller venue, with a crackerjack band content to stay on the sidelines allowed Bob to rejuvenate his muse and his career. Making for a series of comebacks that will be covered next week, leaving behind the half-hearted desperation of the eighties.

Still there are those who claim that there are some hidden gems scattered among the dross of this decade, but no one has ever really argues that his work at this time was terribly consistent. In fact, most of his his best material from this period, (like say Blind Willie McTell) would end up being cut from the album it was originally intended for and left until the official Bootleg Series to see the light of day.

So… Bob found God.

And, as always, when Dylan gets into something he gets really into it. But he must’ve know this Jesus thing was going to be a tough sell, so he hired Jerry Wexler to produce and Mark Knopfler to guest on what would turn into Slow Train Coming. And it worked. Maybe people were so glad that the album wasn’t recorded in a rush and turned into a half-hearted mess, like the last album Street Legal that they were willing to overlook the preachiness of the songs. At least Bob sounds really excited and invested in what he was singing about for a change.

But as Bob refused to play any of his secular tunes in concert, and a second album of gospel titled Saved came out, the patience of the audience and the critics quickly waned. It didn’t help that Saved ended up with nearly as muddy of a mix as Street Legal. The tide had turn on Dylan’s born-again period.

By the third album, even Dylan was getting a little tired of this. Older, non-Jesus songs were popping up in the live set again. And the third album in his Christian trilogy, featured straight-forward love songs like Heart Of Mine and even a whole song about decidedly non-christian comic, Lenny Bruce.

And then just like that – without any announcement or fanfare – the Christian period was over and Bob never really addressed it again. Did he still believe, and was just not singing about it anymore? Or did something happen that made him question, or even renounce, his faith? Who knows?

But coming into the eighties, Bob wasn’t quite sure who or what he was making music far any more. As a result, this born-again period soon looked back on with an air of wistfulness.

While most of Pat Garrett & Billy the Kid‘s soundtrack seemed to be more of the directionless confusion of Dylan’s early seventies, there was one song that stood out amongst the instrumentals and multiple versions of the plot summary song: Knockin’ On Heaven’s Door. This song not only jolted Bob out of this creative malaise, but also reignited the public’s interest.

Maybe his kid was finally old enough, or maybe he was just bored of being home all the time, but in 1974 Dylan decided to go back on tour. While he had done two or three one-off shows in the meantime, this would be Bob’s first tour since the ’66 motorcycle crash. Once again using The Band (who were now stars in their own right) as his backing group, Tour ’74 was going to be the must-see event of the year. So, Dylan quickly recorded Planet Waves beforehand so he would have something to sell along the way. While not a great record, it was certainly less of a confusing mess than any he had done since the sixties. Plus it included Forever Young, a song so good he couldn’t decide how to arrange it and put it on the album twice.

The tour was a big success financially, but kind of disappointing creatively – especially to Dylan. But it did get him out of the house. Which did get him in trouble with the wife, Sara, who left him. That in turn inspired his deeply personal Blood On The Tracks. Which resulted in Sara coming back to him. But Dylan didn’t want to make the same mistakes on this next tour, which was dubbed “The Rolling Thunder Revenue.” Instead of a well-planned highly commercialized affair, this would be more of a merry ragtag gang of traveling performers, wandering aimless and pitching their circus tent where they may. As usual, an album who quickly recorded to sell at shows, but Desire had its lyrics mostly co-written by playwright Jacques Leavy to keep them from being as personal as his last album.

The tour was going to include many of his old Greenwich village compatriots, included ex Joan Baez. To keep Sara from getting jealous (or himself from getting tempted) he brought his wife along under the pretense of filming a movie as chaotic and brilliant as the tour itself. The resultant film, the four-hour Renaldo & Clara was certainly chaotic, but nowhere as coherent as the tour. Even with Sam Sheppard along for the ride supposedly “writing” the movie. Plus, Sara finally had enough and divorced Dylan. The resultant movie flop and alimony left Bob in a financial hole. So he was ready to do whatever was needed to increase his cash flow again

Enter “Vegas Dylan” – it’s Bob with a horn section and trio of backing singers doing slick, if somewhat perverse arrangement of his greatest hits. A pre-tour album called Street Legal was recorded using this new big backing band. While the horn section ultimately got whittled down to a single saxophonist, the gospel styled vocal trio remained. This is important because one of these singer was a true died-in-the-wool Gospel singer and a devout Christian too. Dylan’s perverse fascination with the one woman who wasn’t interested in him, would ultimately lead to the next series of albums… Bob Dylan becomes born again.

In retrospect, it is easy to see Self Portrait as an attempt by Dylan to shed himself of the burden of being the new hippie messiah. With its collection of slick country covers, overdubbed folk jams, and sloppy live tunes, there was no way this double album could be anything but off-putting. How intentional or subconscious it was on Dylan’s part is hard to say. Either way, instead of ridding himself of his audience, he merely riled it up. Four months later, he released New Morning, which was seen as something of apology, since it was a single disc of all originals. However when the Dylan album came out in 1973 with a bunch of outtakes of covers from these sessions, it became clear that Bob was having some sort of writer’s block.

For the next few years, Bob pretty much gave up on recording altogether. This was a much longer dry-spell than the radio silence that followed the motorcycle crash. And even that was filled with all sorts of unheard Basement Tapes. However, after eight years of pretty constant activity, all Dylan managed to do in 1971 and 1972 was a couple of new songs as bonus tracks for a greatest hits compilation and a one-off return to protest music with the single George Jackson. For all intents and purposes, Bob was a washed up has-been by 1973 when he decided to make his next record.

But his next record was going to be a soundtrack to a Sam Peckinpah western, which meant that Dylan wasn’t going to have to come up with the subject matter for his next project himself. And when Pat Garrett & Billy the Kid came out, it featured very few words from the preeminent wordsmith. Instead, the album primarily consisted of instrumentals; which probably was a nice and easy way for Dylan slowly dip his toe back in the album making world.

However there was one song with words, that was going to change everything and issue in the next phase of Bob’s career and a return to form in a lot of ways.

In 1966, Bob got into a motorcycle accident. Reports vary wildly about exactly how bad the injuries were, but either way this was a wake-up call for Dylan. Either that, or it was an excuse to escape the rat race. Whichever it was, Bob cancelled all plans to keep touring (and getting booed at), pumping out albums and singles, and generally burning himself out. He had secretly gotten married and had a kid at this time, and wanted to spend some time with them at home.

But Bob didn’t want to spend all of his time at home. This wasn’t John Lennon retiring to become a househusband and raise his son, Sean. Dylan needed to get out of the house occasionally. Luckily, his band (soon to be The Band) were still on retainer, so they rented a big pink house near Dylan’s in upstate New York, and every day, Bob would wander over and they would all jam and record the proceedings. Some were for submission as potential songs to be recorded by other artists. And a lot of them were just for fun, with no thought given to whether anyone would ever hear them. These eventually leaked out into the booming bootleg market, until being finally officially released in 1975 as The Basement Tapes.

While those tapes may not have been meant for public consumption back in the sixties, Bob wasn’t done with recording and releasing albums. He was just done being public figure, much less a rock-star. His first release after the motorcycle crash was John Wesley Harding, a sparse acoustic album released at the end of 1967, the year of Sgt. Pepper and the “summer of love.” It was the exact opposite of what was popular at the time, but Jimi Hendrix turned All Along The Watchtower from this album into something more in line with the current zeitgeist, and the tune became something of a hit for Dylan despite not being released as a single.

His next single, would be a relative hit for him, Lay Lady Lay. Written for the movie, Midnight Cowboy, but not finished in time, this tune featured Bob in his new country-mode. Bob went full-on C&W, the most un-hip, square, redneck thing he could do. Maybe he was deliberately trying to torpedo his career, but the song proved to be so good and catchy, that it became quite popular despite of itself. If Dylan was going to try and alienate his fanbase in an attempt to get some personal privacy, he was going to need to get much more off-putting. And so began the sessions for Self Portrait.

And if you want to hear all about that particular record, go HERE.

This is where Dylan makes it big. This is the Dylan that everyone knows. The one constantly wearing sunglasses and being a complete jerk at every press conference. The one with the crazy hair. The Bob Dylan who was booed for “going electric.” The one that they would try and make into a movie starring Timothée Chalamet.

And this is undeniable one of the very best, top-form, all-time great Bob Dylans. In fact, he was operating at such a high level at this point, that many Dylan fans have a hard time getting past this and enjoying anything else he’s done since. Which is hogwash. There are some really weird and interesting periods coming up in the future. But this is certainly the Dylan cemented his reputation with and gain the clout and cultural capital necessary to make all the subsequent left turns and about-faces.

Despite flirting with playing in a band earlier, Dylan really kicked off this period with the opening shot of Subterranean Homesick Blues with its famous one-take, B&W, non-lip-syncing video where he just hold hand lettered signs of his lyrics. As usual, the song title is not actually in the song itself. Sometimes you have to tell people that it’s called Rainy Day Women #12 & 35 and not “Everybody Must Get Stoned.”

This is where Bob recorded Like A Rolling Stone and did not record Eve Of Destruction or Stuck In The Middle. Even if he still wasn’t having #1 hits, everybody now wanted to be Bob Dylan. For every die-hard folk fan who turned their back on Bob, he gained five acolytes who shamelessly copied him when he “went electric”.

And there are some really good music. Usually it’s just three chord blues structures married to these Kerouac-influenced lyrics and stretching way beyond the usual three minute limit for a pop song.

Bob had become a huge rock star, and the number of concerts and recordings and appearances would be impossible to pull off without a steady stream of hallucinogens and psychedelics and amphetamines. And there was no way to keep this up forever. Bob needed an exit ramp from the fast lane, and there was going to be a bit of burning up upon re-entry. But it may have been necessary for survival.