The Ugliest Bob Dylan Records in the World

Empire Burlesque 

Knocked Out Loaded

Down in the Groove 

Dylan & the Dead

Under the Red Sky 

This summer Bob Dylan is touring as part of Willie Nelson's Outlaw Festival. There's been a lot of buzz around this tour given the fact that it's the first post-Rough and Rowdy Ways shows, which had a very limited set list centered (mostly) around the songs from his most recent album. Before Dylan started touring with the festival, people online started speculating whether or not Dylan would just perform the same songs he's been performing for the last three years? Prior to the Rough and Rowdy Ways Tour Dylan would perform an ever-changing set-list (almost) every night as part of what is commonly known as "the Never Ending Tour" (1988-2019 RIP). Would he return to that type of concert? After about a month of touring, it's clear that he's definitely playing a new setlist of old songs and covers, although he's pretty much stuck to the same set of songs and covers each night. 

Two highlights of each show are the performances of "Shooting Star" and "Under the Red Sky," songs from Oh Mercy and Under the Red Sky respectively. These songs are special to me because they come from the period in which I got into Dylan's music. Though I first discovered Dylan's music from my mom's vinyl copy of Greatest Hits, I first became aware of Dylan from MTV, USA for Africa and music videos in general. This might seem ridiculous because Dylan appears to be an artist who didn't necessarily take to the medium particularly well, but I have a distinct memory of seeing the video for "Jokerman" one afternoon on a local music video show (such things existed for the kids who didn't have access to cable).

I was 14 in 1988 when my serious Bob Dylan interest began. I saw him live that year, about thirty or so shows into the Never Ending Tour. His then latest album Down In the Groove would be named the worst album of the year by Rolling Stone. The next year he released Oh Mercy, which would be named one of the best albums of the year by Rolling Stone. Oh Mercy was the first good Dylan album that was mine. It was the first demonstration in real time what people had celebrated in Dylan's sixties albums: the use of language, the murky mythology, the ability to write songs that sounded as if they had existed forever. And the production was different from what I had heard from Dylan in the 1980s: gone were the drum machines and the blues rock, in came the famously swampy reverb of Daniel Lanois production. Dylan sounded relevant, if older, and artist who could still be as cool as he had ever been. 

So, naturally, I was very excited for his next record titled Under the Red Sky. In those days the only information you would have about an upcoming release was usually an album title followed by a blurb in Rolling Stone. I knew from said blurb, for example, that the new album would be produced by Don Was, from the group Was (Not Was). Was (Not Was) had a minor MTV hit with their song "Walk the Dinosaur" from the album What Up Dog? I had the cassette and I'd still defend that record. Like so much of Was (Not Was) the album is a strange mixture of avant-skronk, dancefloor bops, neo-soul and Frank Sinatra Jr. The band itself has in the 21st century acquired some cache for their work in the early 80s, pioneering the mutant disco genre giving it one of its enduring themes "Out Come the Freaks." 

When the first single/video from the Dylan album dropped, "Unbelievable," I was disappointed. I believe the album was panned, again, by Rolling Stone and it was quickly forgotten. His next album would be all acoustic covers, Good As I've Been To You, but it was too late. I had lost interest in Dylan's new records from that point on. It didn't help that a year after Under the Red Sky Dylan released the first three volumes of his Bootleg Series, containing then unreleased masterpieces from his then thirty years of making music. Why listen to the new stuff when you could listen to "Blind Willie McTell" or "She's Your Lover Now" or "Series of Dreams," unreleased songs that ranked with the best of his work. Shortly after Good As I've Been to You came another covers record World Gone Wrong followed by MTV Unplugged. In my mind Dylan had become a nostalgia act, happy to resurrect his career as a folk troubadour, while also milking his mid-sixties hits for a Gen X audience at venues like Woodstock 94. 

While I didn't mind any of this stuff, I hardly thought it was as interesting as what Dylan's old friends/rivals were doing at the time: Leonard Cohen had released two of his best albums in I'm Your Man and The Future, both of which sounded weird, electronic and both out of and born in time. Neil Young had started a string of amazing comeback records: Freedom, Ragged Glory, Harvest Moon, Sleeps With Angels plus a couple of blistering live albums, Arc and Weld, the former of which had more in common with Sonic Youth (who toured with Young around this time) than Dylan's MTV Unplugged (Neil would do his own Unplugged during this time too, but even then Neil proved to be far more adventurous in his song selection, choosing "Transformer Man" from 1981's bat-shit electronic album Trans as the first single and video from the Unplugged set). 

The nadir of Dylan's career for me came in 1993 when Dylan rounded up many of his contemporaries for a thirtieth anniversary tribute show, praising the great and powerful Dylan, and performing for him and us for free. It didn't help that this was taking place the same year that PJ Harvey released Rid Of Me, covering "Highway 61" with a manic energy that none of the thirtieth anniversary performers captured in their mostly reverential performances (though, Lou Reed's "Foot of Pride" came close, and Sinead O'Connor's rehearsal performance, though not manic, comes closest to besting Dylan's original). This period of Dylan's career so soured me on the man and his music that I initially didn't listen to his great "comeback" album Time Out of Mind because I was convinced it couldn't be that good. It took me a while to listen to most of his late 90s and 2000s music because I just assumed it wouldn't be as good as what came before. 

Thinking about this now it doesn't seem that unusual to me. It seems much more unusual that younger people would have been expected to listen to and enjoy music made by musicians who had careers before they were born. At the time, "classic rock" functioned like Stockholm Syndrome: not only did boomers argue that their music was still relevant, but that it was actually better than most of the stuff younger musicians were making at the time. The period from 1987-1994, from the twentieth anniversary of Sgt. Pepper's and the Summer of Love to the twenty fifth anniversary of Woodstock, was both the apotheosis of this idea and, I would argue, the end of the idea as well (when people think about Woodstock '94 they mostly remember Green Day's performance in the middle of a mud fight. Though Green Day is nostalgic for earlier music in its own way, the dominance of their performance suggested a changing of the guards). This period also covers most of the time period in which Bob Dylan was making the ugliest Bob Dylan records in the world. 

Empire Burlesque

If you're thinking of the quintessential "80s" Dylan record, you're thinking of Empire Burlesque. The first single, "Tight Connection To My Heart (Has Anybody Seen My Love) has the gated drums, the synth pads, the back-up singers that mark the "classic rock" of the era. It sounds like Dirty Work by the Rolling Stones, hints at the much more commercially successful Brothers In Arms by Dire Straits (Mark Knopfler had produced Dylan's previous studio album Infidels), more often than not flails around like Rod Stewarts music from the time. "Tight Connection" even had an MTV video in heavy rotation directed by Paul Schraeder that is brilliantly absurd with its Miami Vice aesthetics, though its also head scratching in its attempt to be contemporary in its very music video-ness. The album is a mess to be sure, but it also works some of the time:  "Tight Connection" is actually one of the catchiest things Dylan had written since the 1960s, a song that could have been a hit if sung by someone who didn't sound painfully middle aged. "When the Night Comes Falling From the Sky" is a great song, and is the actual successful blending of 80s production (the album was produced by Arthur Baker, who had worked with everyone at that point) and Dylan's lyrical qualities. It sounds like a New Order 12" with a guest lead vocal from the man himself. It also sounds like a blueprint for what Leonard Cohen would do on I'm Your Man. If anything, I wish more of the album sounded like this. Reportedly, Arthur Baker thought Dylan should end the album with an acoustic number and Dylan wrote "Dark Eyes" in a night. If you miss the old Dylan, it's probably the best thing on here.

Knocked Out Loaded

When Bob Dylan was awarded the Kennedy Center medal of honor, Gregory Peck presented the award to him, which I'm sure made Bob very happy, but must have been confusing to any number of people watching at home. This album is the reason why Gregory Peck presented him with that prestigious award. Nevertheless, this is probably, legitimately Bob's worst album. It also happens to have one of my favorite Bob Dylan songs in "Brownsville Girl," the song about seeing a movie starring Gregory Peck. It also has absolutely forgettable songs like "You Wanna Ramble" and truly excruciating songs like "They Killed Him," which might be the worst Bob Dylan song. The way his vocals are recorded on this record, he sounds lost, alone with only his voice accompanying him in an echo box. "Driftin' Too Far from the Shore" is probably the only other good thing on here, but it's just a kind of pleasant dated soul-rock number that wouldn't have sounded out of place on Bruce Willis' The Return of Bruno released around the same time. "Got My Mind Made Up" isn't bad and is elevated by the co-writing credit of Dylan's young friend Tom Petty. Much better are the recordings of the concerts Dylan played with Petty and the Heartbreakers around this time.

Down In the Groove 

This was the record Bob Dylan was "touring" when I saw him live in 1988. He only played two songs from the record "Had A Dream About You Baby" and "Silvio," which perhaps reflected his own feelings about the record. I have to admit, perhaps because I saw him on this leg of the Never Ending Tour, Down In the Groove might be my favorite of Dylan's Ugliest Records. By 1995 Nick Cave & the Bad Seeds had recognized the greatness of "Death Is Not the End." I see this song as Dylan's own response to Cohen's original recording of "Hallelujah." "Silvio" was co-written with Dead lyricist Robert Hunter, with the Dead providing backing vocals. It was the highlight of the show I saw, stayed in my mind for a while, and was finally rewarded with a place on Greatest Hits Volume III (more on that later). Much of the album consists of covers "Let's Stick Together," "Shenandoah," "Rank Strangers to Me," the later two of which are quite good. Is it a good Bob Dylan record? No! It's ugly! But being the ugliest girl in the world is its own reward, I guess. Oh and yeah this is the record that has "Ugliest Girl in the World," where I cribbed the name for this essay.

Dylan and the Dead

The Grateful Dead had almost the opposite experience of Bob Dylan in the 1980s: since the Dead had been a touring band for most of the 1970s and had built up an international following in that arena, they were never really dormant during the decade (unlike Dylan who toured in spurts in the 1980s never to Dead-size crowds) and could always rely on their audiences supporting them. Although I will defend most Dead studio albums, they were never known as album artists the way Dylan had been. Yet, in 1987 the Dead had a huge single and video hit with "Touch of Grey," got a whole new generation of fans, and started playing in the largest venues of their career. "Touch of Grey" is one of their great songs and the album it comes from, In the Dark, is fine, however what is fascinating is that it's no less dated in its sound than Empire Burlesque and Knocked Out Loaded. Additionally, Dylan had Tom Petty and Arthur Baker working with him--an artist and producer who were very popular at the time--whereas the Dead were working within their organization, not attempting to reach out to any audience younger than their already established one. 

So while a decade earlier the Dead and Dylan would have been on equal footing as support for one another should they have toured together, when the Dylan and Dead tour took place in 1987, and an album from the tour was released in 1989, it could have seemed as if the Dead were helping their old friend/mentor Dylan out at a low point in his career as they ascended. A lot of people dislike Dylan and the Dead. A lot of people will tell you that there are better shows from which they could have drawn (check out the show from Autzen Stadium in Eugene, OR) and both groups have strong arguments. Dylan seems very checked out on these shows. The Dead clearly want to do what the Dead do best: jam. However, every time Jerry's about to go into a flying solo, Dylan steps on his playing and moves on to the next rote rendering of whatever verse or chorus the song requires of him. Also, "Joey?" Really? That said, the stuff from the gospel period is performed really well ("Serve Somebody" "Slow Train Coming") and the song that sounds as if it should have come from the gospel period ("Knocking on Heaven's Door") is great as well. 

Under the Red Sky

In 1994 Dylan released Greatest Hits Vol. III, an almost inexplicable Greatest Hits compilation for which no one asked. Brief history of the Dylan greatest hits series: In 1967 Columbia Records released Greatest Hits, a stop-gap cash grab the label put together while Dylan (ostensibly) was recovering from his motorcycle accident. The only reason anyone needed this record in 1967 was for the until then unreleased "Positively 4th Street." That said, this was the first Dylan record I ever heard (from my mom's long-forgotten vinyl collection back in my grandparent's apartment), commencing my life-long love of Dylan, and I guess, as a starting point, you could do much worse. Greatest Hits Vol. II made more sense: unreleased songs, deep cuts, "Quinn the Eskimo" "rescued" from Self-Portrait, I don't own a copy but people generally like it and some of the then new songs "When I Paint My Masterpiece" and "Watching the River Flow" have become staples of Dylan's live show for years. 

Dylan didn't release another Greatest Hits record for twenty-three years. Arguably he didn't need to: other than a few songs here and there breaking through, Dylan didn't really have hits the way he did in the mid-to-late 60s. He had, essentially, become a cult artist and cult artists don't really have "hits." In the mid-1980s Dylan released Biograph, a box set of well-known songs, unreleased songs that would serve as a new paradigm for how artists like Dylan would present their entire careers beyond just the "greatest hits" (think Bowie's Sound + Vision or Lou Reed's Between Thought and Expression box sets). 

There really was no need for a Greatest Hits Vol III in 1994, but, somehow, the collection of songs transcended that need. Indeed, it was odd to think that neither "Knocking On Heaven's Door" nor "Tangled Up in Blue" had been on a Greatest Hits set before this point. Both those songs as singles had made the top 30. So would "Hurricane" and "Serve Somebody." So, depending on how far you wanted to stretch the word "hit," there was some justification for the compilation. However, it wasn't the hits that made the record special for me: "Changing of the Guards" was an amazing Dylan song I had never heard because of the low opinion critics had of Street Legal. I stayed away from the born-again records (again because of low opinions) but "Groom Still Waiting at the Alter" (a b-side from Shot of Love) was one of the best Dylan rockers I had heard since the 60s. No "Tight Connection," (which charted slightly below the top 100) but the ugliest records are proudly represented by both "Silvio," which I fondly remembered from my 1988 concert, and "Brownsville Girl," which was an absurdist, self-referential western complete with female backing greek chorus that was a hoot and proved that Dylan could be very funny when he wanted to be.

Sandwiched between "Brownsville Girl" and the closing "Knocking On Heaven's Door" was the inexplicable choice of "Under the Red Sky." It wasn't a single, as mentioned before that was "Unbelievable" from Under the Red Sky, I don't think it was a fan favorite and the impression I had listening to it for the first time was, with reference to and reverence for Greil Marcus, "what is this shit?" A weird-ass song about homeless children, the moon, said children getting baked in a pie and, eventually, environmental devastation. There seemed to be an oblique Paul Simon reference--"a diamond as big as your shoe"--and the whole thing stuck out like a sore thumb (plunged into a children pie) along side of the other forgotten "hits" of the compilation. I hated it, and, by extension, I hated Under the Red Sky having never listened to the album. I wasn't alone in having a low opinion of the record: with the exception of rock critic Robert Christgau and Dylan scholar Clinton Heylin almost everyone thinks it's one of Dylan's worst. 

This essay was inspired by the Jokermen podcast, which recently did a re-evaluation of Under the Red Sky (after a similar re-evaluation of Down in the Groove). It's clear now that Under the Red Sky has at least one of Dylan's great songs of the period: "Born In Time," a song we later found out had been written during the Oh Mercy sessions. I would argue that "God Knows," a song Dylan regularly played on Sunday while touring in the early 90s, including his famous Woodstock '94 performance, deserves to be ranked highly as well. I can appreciate the humor of songs like "Handy Dandy" and "Under the Red Sky" now that Dylan's 21st century career has more bizarrely humorous songs. "Cats In the Well" is a good rocker that plays well live. I wouldn't say it's my favorite of the ugliest albums period, more like the second ugliest girl in the world.