Bob Dylan’s catalog teems with landmark albums, many of which are ranked by experts among the finest of all time. That wouldn’t be the case if Dylan didn’t have a knack for picking the perfect songs to close out these records and send people out wanting more.
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Narrowing the list of the best Dylan album-closers is no easy feat, but we gave it a shot anyway. Prepare to argue, and prepare to marvel at some of the songs that did make the cut.
5. “Sugar Baby” from Love and Theft (2001)
Most of Love and Theft is reserved for rollicking, blues-based ramblers. But as this list will make clear, Dylan has always liked to ease back on the pace a bit on the closing tracks for solemn rumination. “Sugar Baby” allows him to do just that. Framed by a series of thudding guitar notes that seem to signify a kind of sad resignation, the song features lyrics that follow in kind with those emotions. Starting out with the evocative line I got my back to the sun ’cause the light is too intense, “Sugar Baby” then goes on to capture the price paid for staying too long in that darkness.
4. “It’s All Over Now, Baby Blue” from Bringing It All Back Home (1965)
You can read this song a few different ways, and it works fantastically no matter your interpretation. It could simply be a song about one half of a couple deciding to leave the other behind, while giving them the advice that they’ll need to carry on. Or it could be Dylan’s coded message to his fans that his music was in the process of changing drastically, and they could either follow along or find another spokesman for a generation. In any case, the narrator shows no rancor toward those he’s leaving behind, even as he makes it abundantly clear he’s already onto the next phase.
3. “Every Grain of Sand” from Shot of Love (1981)
A few of the songs on this list not only ended albums, but they also signaled an end to a certain style of music that Dylan was about to shed. In the case of “Every Grain of Sand,” it was the last song on the last overtly religious album within his “born again” period. With this track, he sent that stretch out on a towering high point. Whereas some of the other songs in this time frame pointed the finger at non-believers, Dylan used “Every Grain of Sand” to look inside himself and assess the difficulties of holding on to his faith. As such, the song unforgettably combines honesty and beauty.
2. “Desolation Row” from Highway 61 Revisited (1965)
It’s easy to talk about this song and get carried away with the lyrics, which are undeniably monumental. But let’s not forget that “Desolation Row” is one of the prettiest songs in the Dylan catalog, thanks to the effortlessly stunning guitar work of Charlie McCoy and Dylan’s mesmerizing singing. With that foundation in place, you really don’t feel like this song takes up 11 minutes of your time. You just get lost in Dylan’s name-dropping and wry observations, all of which seem like a way for the narrator to cover up a deep personal sadness.
1. “Sad Eyed Lady of the Lowlands” from Blonde on Blonde (1966)
Here is another case where Dylan seemed to be giving hints with an album-closer about where he was heading. In the case of “Sad Eyed Lady of the Lowlands,” the sauntering, mammoth love song to then-wife Sara seemed to suggest that domesticity was waiting, and the hyperactive pace he had kept in the previous years had run its course. The recording was notable because of how Dylan kept the players in a state of nervous energy, waiting for the signal the song was going to end. You can almost picture them all with the narrator, serenading her while waiting at the Sad Eyed Lady’s gate.
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