9 min read

Counting Down Bob Dylan’s Music Videos

A Comprehensive Ranking
Counting Down Bob Dylan’s Music Videos
Tight Connection to My Heart (Has Anybody Seen My Love), dir. Paul Schrader

This week, I’m working on a book chapter concerning Bob Dylan’s music videos, an eclectic and odd collection of work. But as I work on this chapter, I’ve come to notice that there’s very little writing on these videos out there on the internet. So today, I thought I’d contribute what—based on the increasingly useless Google—might be one of the few attempts to comprehensively rank Dylan’s music videos. Plus, I love thinking about these, and it’s fun to do so casually on a day when I'm not writing about them in an academic parlance.

Before we get to the countdown, there are a couple of

Videos I’m Ruling Out

These are both collage-style videos made to accompany archival tracks. They’re cool! Visions of Johanna was directed by John Hillcoat, of all people! But they’re not necessarily worth discussing in the same breath as the balance of the videos.

Bringing in these videos would just be too much to wrangle. Plus, every Wilburys video is essentially a variation on the same theme (Hey, look! The Traveling Wilburys!) so they’d all sit clumped in the middle of the list.

This iconic piece of work features Bob prominently but it’s certainly not “a Bob Dylan video.”

Speaking of “not a Bob Dylan video”, there would be no reason to consider this in a ranking, but I just need to mention–for the sake of comprehensiveness–that Bob did make a brief and silent cameo in this video. It’s bizarre in its incongruity, but it’s delightful.

Honorable mention

  • Most Likely You Go Your Way (And I’ll Go Mine) (Mark Ronson Remix) (2007)

Now this isn’t necessarily “a Bob Dylan video” so much as a Mark Ronson one, but it’s really cool. This is one of a variety of videos designed to draft off the iconography of Dylan, this time showing a faceless Dylan stand-in moving semi-magically through the iconography of the man’s life and times, from Greenwich Village to the ‘66 world tour to the motorcycle crash to Rolling Thunder and beyond. It’s really well done, and it’s sort of thrilling to see the decades stream by in one sustained flow, but it also feels a little tangential to “the Bob Dylan video project.”

  • Subterranean Homesick Blues

There’s not much of an argument that this is a music video—it’s the opening scene of a movie, D.A. Pennebaker’s Dont Look Back—but there are those who credit it as a forerunner of what we now call the music video, so it’s worth nodding at. Also, it’s just cool.

Now for

The Official Ranking

20. Beyond Here Lies Nothin’ (2009)

Dylan has collaborated on four videos with Australian director Nash Edgerton (brother to Joel). This one initially seems perfectly promising, a man arriving home to his rundown apartment. But within moments it’s clear he’s been holding a woman captive—and she’s escaped. The remainder of the video is a brutally graphic brawl between the two of them, one that climaxes when she hits him with her car, then hops out to begin making out with him. How unpleasant is this video? It’s competently made, but it’s just ugly from top to bottom.

19. Little Drummer Boy (2009)

The lesser of two videos for Christmas in the Heart, this is an animation exercise, and a lovely one, but it’s not necessarily a compelling music video, let alone one for Bob Dylan.

18. Jokerman (1985)

This video was co-directed by Larry “Ratso” Sloman, a frequent hanger-on of Dylan’s over the years. When he got his crack at a video, Ratso presented a more or less random assemblage of imagery—Hitler; the atomic bomb detonating; a Picasso. In between, we occasionally get glimpses at Bob in his Miami Vice finest—white tee under cream blazer—but it’s all about the montage, and the montage is nothing.

17. Not Dark Yet (1998)

A real video in search of a concept—Bob is distorted; there are seemingly random street shots. It never coheres, and you really feel the six-and-a-half minutes.

16. When the Night Comes Falling From the Sky (1985)

A lot of Dylan’s ‘80s videos are pretty low concept—just stick Bob on a stage and hit record—and this one most of all. There are some real iMovie-type video effects, but  that’s about as lively as things get.

15. ‘Cross the Green Mountain (2003)

This one is a tie-in with the largely forgotten movie Gods and Generals, and in between battle shots from the film (free production value!) we see Bob in Civil War drag walking among the dead and wounded, offering sympathy, and finally posing for a portrait photo. It’s a dreary affair, though there’s something perversely compelling in the obviousness of Bob’s wig, and the intensity of focus he brings to the role.

14. Don’t Fall Apart On Me Tonight (Version 2) (1983)

This video has an exciting pair of directors in legendary documentarians Albert and David Maysles. Accordingly, this is a documentary-style video, just capturing Bob and his musicians in the studio. There’s nothing to dislike here—there’s just not all that much to like, either, give or take your interest in ‘80s recording studios.

13. Emotionally Yours (1985)

Like When the Night Comes Falling From the Sky, this video is co-directed by Markus Innocenti, and it functions as something of a companion piece—monochrome, a simple focus on Bob doing his work—but there are a few touches that elevate it, including the evocative empty-theater backdrop, and an eerie effect created by using an actress to recreate a picture of Elizabeth Taylor. There’s an incongruously bizarre moment in which Bob watches a woman hang from a trapeze that dangles from a tree only for her to run off, leaving him despondent. It doesn’t all hang together, but there’s enough there to like.

12. Blood in My Eyes (1993)

This video is sort of an illustration of the cover of World Gone Wrong—Bob, wearing the top hat that he sports on that album, strolls down a street, meeting and entertaining passersby, while intercut we see him singing the song through various distorted effects. It’s simple, but it’s watchable.

11. When the Deal Goes Down (2006)

One of the few videos on this list to not feature Bob at all, this one is helmed by Foxcatcher director Bennet Miller, who shoots Scarlett Johansson in a variety of idyllically romantic contexts through an 8mm lens. It’s all rather lovely, even if it doesn’t build to anything in particular.

10. Sweetheart Like You (1983)

Bob Dylan’s first MTV-era video (it premiered two years after the network did) is another low concept affair—Bob and his band perform in a restaurant after closing time; a woman holding a broom watches them appreciatively. There’s a pleasant atmosphere to the proceedings, and for an early example of the form, it’s low-key pleasant.

9. Things Have Changed (2000)

Another tie-in video, this one attached to Curtis Hanson’s Michael Chabon adaptation Wonder Boys, for which Bob wrote this song, winning an Oscar for his trouble. As movie tie-ins go, this is a pretty good one. Bob represents something like the spirit of Michael Douglas’s character, being dropped into scenes from the movie alongside the actors (Robert Downey Jr, Tobey Maguire, and Katie Holmes), while we cut periodically back to Bob capering in the dark in front of a diner clad in a straw boater. It’s got more momentum and imagery than a lot of these videos, even if it’s largely culled from another source, and Bob’s performance is committed and lively, which you certainly can’t say for every entry on this list.

8. Political World (1989)

From director John Mellencamp, we have a pretty straightforward late-’80s music video: a group of high-powered operatives sit around a baroque table presumably discussing world-shaping events, and who is their entertainment? Bob Dylan, of course. Bob’s outfit is really remarkable—seemingly a long-sleeved white T under a short-sleeved white T—enlivening what’s otherwise a bit of a one-note video.

7. The Night We Called It a Day (2015)

Another Nash Edgerton project, with Bob this time starring in a noir pastiche. There’s guns, molls, double crosses, the works. It’s all appealingly shot as a tribute to classic gangster fare, but if I’m being honest, it’s also a little indistinct—there aren’t many images that linger in the mind, with the whole thing just fading into a generalized noir haze by the time it ends.

6. Unbelievable (1990)

This is pure, uncut chaos, and I love it. One of the few Bob Dylan videos that feels like a classic MTV video, we see several threads braided together—a man experiencing various trials while driving around a convertible; Bob chauffeuring a pig in a limo. It’s joyous, even if it’s impossible to get your hands around before it slips into some new image and idea.

5. Most of the Time (1990)

Bob collaborated with his son, Jesse, on this one, with Jesse getting his first directing credit before going on to direct movies like American Wedding and Kicking & Screaming (the Will Ferrell one). Bob is styled to evoke the ‘65/’66 firebrand, even if, by 1990, that guy was pretty definitively in the past. This isn’t the album version of the track, but rather what sounds to be a live recording. It’s thrilling.

4. Series of Dreams (1991)

On the one hand, this is a pretty low-concept video–it’s a montage of footage mostly culled from Dont Look Back, and Dylan’s own directorial efforts, Eat the Document and Renaldo and Clara. We see imagery from the movies streak by with various effects applied, all while the song’s lyrics appear on the screen.

So what’s exciting about that? Well, if you’ve been immersing yourself in this stuff like I have, it’s very exciting to consider that in 1991, Eat the Document and Renaldo and Clara were basically impossible to see. So you’re getting glimpses at footage most people aren’t familiar with at all, and it’s depicting Dylan at a couple of creative peaks. The song, which describes exactly what the title says—a series of dreams the singer has experienced—is a beautiful match for this central idea that Bob is dozing on a train during the ‘65 tour, dreaming the ‘66 and ‘75 tours. It’s corny, it’s cheesy, it’s one for the Dylan heads. I’m a corny, cheesy Dylan head. I think this video is really effective.

3. Duquesne Whistle (2012)

Nash Edgerton is back in the saddle, and this video is just charming as all hell. It’s like a mini Jacques Demy movie, with a man dancing his way through the process of wooing a pretty lady, only to find his attempts thwarted by various violent digressions. There’s a buoyant charm to the central performance, and this one actually has some ideas and momentum. A joy all around.

2. Tight Connection to My Heart (Has Anybody Seen My Love) (1985)

When Bob Dylan met Paul Schrader. Kind of three videos going on at once here–in Japan, Bob is enmeshed in some kind romantic intrigue, while simultaneously roaming the streets, while simultaneously performing onstage–but the location photography is evocative, and you absolutely have to give it up for Bob’s attempt at choreography in the closing moments.

1. Must Be Santa (2009)

Look, I have mixed feelings about putting this video here. More than anything, it’s probably a testament to the fact that Bob has never made a truly great video. Putting Must Be Santa at the top of any list is damning the whole list with faint praise.

But hear me out.

Nash Edgerton is Bob Dylan’s most fruitful collaborator, so it should be one of his. The best Bob Dylan video should feature Bob Dylan prominently, which means it’s between this, Duquesne Whistle, and The Night We Called It a Day, and neither of those really sits comfortably at the top of a list.

And so we have Must Be Santa.

Yes, this is essentially a novelty video for a novelty song off a novelty album. On the other hand: has any video so effectively captured Bob Dylan the prankster? Bob Dylan the guy who wanted to make an HBO sitcom for a time? Bob Dylan the absolute top-to-bottom weirdo we all love so much? I look at Must Be Santa, and I look at a bunch of people having a great time making something with pretty solid production values. This video is a delight. It’s one of the more gonzo music videos ever produced by a classic rock artist. And it’s the best Bob Dylan music video.