The Four Most Disappointing Bob Dylan Albums

When you create dozens upon dozens of albums, it’s inevitable that some of them will end up, in a word, disappointing. That’s true even if you’re 10-time Grammy-winner Bob Dylan.

One thing to know about Dylan is that he’s never shied away from making the album he wants, regardless of what his fans, colleagues and essentially everyone else might wish of him. In many cases, this works out just fine, landing the songwriter near the top of the charts or at the very least earning praise from critics. But in other instances, the resulting LP is simply a let down, a collection of songs that doesn’t feel like much of a collection at all.

Ultimately, this says less about Dylan’s talent as it does his ability to continue evolving his career, but for the purposes of this article, we’re taking a look at the Four Most Disappointing Bob Dylan Albums.

Self Portrait (1970)

It stands to reason that if you purposefully set out to make a bad album, it will be received poorly, which is exactly what happened with 1970’s Self Portrait.

By that point, Dylan was just about fed up with the swarms of people hoping to catch a glimpse of the person they viewed as the “spokesman” of the ’60s. Dylan was over it, eager to move on both personally and professionally.

“There’d be crowds outside my house,” he explained to Rolling Stone in 1984. “And I said, “Well, f*** it. I wish these people would just forget about me. I wanna do something they can’t possibly like, they can’t relate to. They’ll see it, and they’ll listen, and they’ll say, ‘Well, let’s go on to the next person. He ain’t sayin’ it no more. He ain’t givin’ us what we want, you know? They’ll go on to somebody else.”

The resulting album was tremendously disjointed and, frankly, weird. Dylan’s singing is hard to listen to, the arrangements absurd and the lyrics practically nonsensical. Dylan’s plan to disappoint his fans worked like a charm, and to really drive the point home, Self Portrait was a double album.

“Well, it wouldn’t have held up as a single album – then it really would’ve been bad, you know,” he said in 1984. “I mean, if you’re gonna put a lot of crap on it, you might as well load it up!”

Listen to ‘Woogie Boogie’ From ‘Self Portrait’

Dylan (1973)

To be clear: we’re not saying that just because an album is disappointing that it’s also objectively bad. But when an album is released by an artist, one expects the artist to be involved in that process, which was not the case with 1973’s Dylan.

Dylan was organized and put out by Dylan’s record label, Columbia, with zero input from Dylan himself. It consisted of outtakes from two of his earlier albums, Self Portrait and New Morning — six covers, three traditional songs and no original compositions.

From our perspective, the songs themselves on Dylan are pretty interesting and worth listening to. There’s a fun rendition of Joni Mitchell’s “Big Yellow Taxi,” for example, but the obvious problem is that none of the recordings were ever meant to be released into the world, not to mention sequenced into album form. But we can’t blame Dylan for this, only Columbia.

Is Dylan a bad album? Not exactly. Disappointing though? Yep.

Listen to ‘Big Yellow Taxi’ From ‘Dylan’

Saved (1980)

Some people might argue that Dylan’s entire trilogy of Christian-influenced albums in the late ’70s into the early ’80s were disappointing. Fair enough. We’re a bit more lenient — there are strong spots, in terms of songwriting and also production, on 1979’s Slow Train Coming and 1981’s Shot of Love.

Our primary disappointment is with 1980’s Saved, which continued the overtly religious lyrical themes of Slow Train Coming but suffered from losing Mark Knopfler as a producer and generally feels much weaker. (We must, however, acknowledge that “Pressing On” is quite a stunning track.) And it’s not that Dylan could be described as insincere in his belief, and his singing on Saved is rather good. But like Dylan, Saved isn’t necessarily a “bad” album, but it’s not one Dylan fans return to often and it wasn’t greeted warmly when it was released.

Dylan was not concerned about that.

“Saved didn’t have those kind of numbers [on the charts, compared to Slow Train Coming] but to me it was just as big an album,” he said in a 1981 interview. “I’m fortunate that I’m in the position to release an album like Saved with a major record company, so it would be available to people who would like to buy it.”

Listen to ‘In the Garden’ From ‘Saved’

Down in the Groove (1988)

Many Dylan fans found 1986’s Knocked Out Load awfully disappointing, and they have a point, though it has the saving grace that is “Brownsville Girl.” What we find even more disappointing is that album’s follow up: 1988’s Down in the Groove.

Sure, Down in the Groove has some stellar musicians on it — Eric Clapton, Jerry Garcia, Steve Jordan, Paul Simonon, Ronnie Wood and more — and yet there’s very little that can be considered cohesive about this release. The high moments, such as “Silvio” do stand out, but the lows are too regrettable to ignore. With Down in the Groove Dylan achieved his lowest-charting album since his 1962 debut failed to chart at all.

To be fair, Dylan was struggling at this time to find his sound after not one but three albums of Christian-inspired music, not to mention the fact that the ’80s weren’t exactly kind to many of the rock musicians who first found success in the ’60s and ’70s. Dylan would eventually straighten things out, but Down in the Groove was a significantly disappointing stepping stone along the way.

Listen to ‘Silvio’ From ‘Down in the Groove’