When I Paint My Masterpiece

The crime novelist James Ellroy, who is known for giant and intricate novels such as L.A. Confidential and American Tabloid, opens his public appearances book readings with a hyperbolic self introduction. Here’s one version:

“Good evening peepers, prowlers, pederasts, panty-sniffers, punks and pimps. I’m James Ellroy, the demon dog with the hog-log, the foul owl with the death growl, the white knight of the far right, and the slick trick with the donkey dick. I’m the author of 16 books, masterpieces all; they precede all my future masterpieces. These books will leave you reamed, steamed and drycleaned, tie-dyed, swept to the side, true-blued, tattooed and bah fongooed.”

Having witnessed a different version of this spiel in person, the introduction works as a way to knock the audience back on its heels, but also to draw the crowd into his world with his unique prose stylings. Another version of this intro, Ellroy says that all of his books can cure cancer and A.I.D.S. It’s over-the-top nonsense, but at the same time, the boastful arrogance is endearing in a way because he’s talking about books. The literary world is usually filled with appearances of hand-wringing and modesty. Instead, this guy says that all of his books are masterpieces; everything he will write will be a masterpiece.

Bob Dylan takes a different angle when considering his own artistic output and the concept of “masterpieces,” commenting on it in the 1971 song “When I Paint My Masterpiece”:

“When I Paint My Masterpiece” is a sister song of “Watching the River Flow” as both were recorded on the same day with the same band assembled by pianist and producer of the session Leon Russell. Both songs find Dylan contending with his own art, upheld by the playing of a shit-hot band. “When I Paint My Masterpiece” highlights the electric guitar and piano in the intro before settling into an easy, engaging groove. Dylan’s vocals are warm throughout as he is comfortable and relaxed within the instrumental setting of the song.

The lyrics depict the narrator’s adventures in Rome and Brussels. A cynical take would be that Dylan wrote the song as a way to write off a trip to Europe on his taxes for fiscal year 1971. Taking away this angle, the European scenes allow Dylan to consider the output of Old World classical artists widely accepted as masterpieces in comparison with his own artistic creations. Dylan sings that in Rome, “Ancient footprints are everywhere.” Any contemporary artist has to walk in the ubiquitous footprints of the masters that come before. The song’s narrator even has “a date with Botticelli’s niece.” Sandro Botticelli was a painter from the Italian Renaissance, and Tony Attwood speculates that Dylan’s line either is a reference to Botticelli using his own niece as a model or that it is Dylan playing off of the name “Venus” in the title of Botticelli’s masterpiece Birth of Venus. Dylan’s next line is “She promised that she’d be right there with me” which could mean that the narrator is promoting the beauty of his traveling companion, one who has the aspect and traits of a female figure from a Botticelli painting. 

Dylan has a vastly dissimilar view of his own work than James Ellroy. As the title of the song suggests, Dylan expresses that he hasn’t produced a masterpiece, so there’s uncertainty about his own production thus far. Though for Dylan, it’s only a matter of time — when I paint my masterpiece. What will happen when the masterpiece is completed? Dylan has two answers. The first — “Someday, everything is gonna be smooth like a rhapsody” — is delivered by Dylan in such a way that matches the words; he sings it smoothly as if the line is from a rhapsody! The second response is: “Someday, everything is gonna be different.” There’s a sense that Dylan can put things behind him when he finally achieves mastery. He’s chasing a high that will bring a sense of finality. I will be a different person; I will feel fulfillment. Like chasing any high, it’s a sucker’s game because as soon as the high wears off, you want it again. This one is a masterpiece. No wait, this one is my masterpiece. 

Dylan had a similar interpretation of “When I Paint My Masterpiece” when asked about the song by Douglas Brinkley during an interview for the New York Times in June 2020:

“I think this song has something to do with the classical world, something that’s out of reach. Someplace you’d like to be beyond your experience. Something that is so supreme and first rate that you could never come back down from the mountain. That you’ve achieved the unthinkable. That’s what the song tries to say, and you’d have to put it in that context. In saying that though, even if you do paint your masterpiece, what will you do then? Well, obviously you have to paint another masterpiece. So it could become some kind of never ending cycle, a trap of some kind.”

As stated above, “When I Paint My Masterpiece” was recorded at the same session for “Watching the River Flow” with the same band. There’s a connection between the messages of the two songs. Taken together, both songs are Dylan contending with his standing as an artist. What do I do with this talent I have? To what end? While considering deep questions about his vocation, “When I Paint My Masterpiece” is also a witty song. The juxtaposition of asking those questions about his own work within the context of the Old Masters is rather audacious and cheeky. Furthering the gag, Dylan does not release “When I Paint My Masterpiece” as a single. Instead, it is included in a compilation later in the same year, Bob Dylan’s Greatest Hits Vol. II. Dylan says in the song that he hasn’t produced a masterpiece yet, but then he includes the song on a greatest hits collection; the second one released in four years, for that matter. A lotta chutzpah there!

Dylan commentator and author Jochen Markhorst commented on the Recliner Notes post about “Watching the River Flow,” sharing fascinating interviews with Leon Russell that were published in Judas! #9 in April 2004. According to Russell, the impetus of the recording session with Dylan was wanting to witness first-hand and learn about Dylan’s process for writing in the studio. As Russell said:

“I begged him and begged him, and after a little while he agreed to show me. So I called my guys…and we went up to Blue Rock Studios in the Village, and I cut these two tracks for Bob. It took about 30 minutes. Then Bob came down, and I said, ‘Let me see you write songs to these.’”

As Markhorst points out, this suggests that Russell wrote the music for both “Watching the River Flow” and “When I Paint My Masterpiece” without receiving a co-writing credit. Russell goes on to say:

“They put the tracks on the tape machine, and Bob got his pad out and started walking around, writing stuff down. I followed him round the room, watching him as he was writing. When it got to the end, they’d rewind the tape and play it again, and he kept writing. And then when he’d got the words the way he liked, he cut the vocals…The key line on the other one was ‘You’ll be right there with me, when I paint my masterpiece’; and I WAS right there with him. It was amazing to watch him do that. I don’t think he normally worked that way. But he endeavored to give me that, as I’d asked to see it happen.”

In 2013, Dylan put out The Bootleg Series Vol. 10: Another Self Portrait (1969–1971) which included a version of “When I Paint My Masterpiece”:

It’s a gorgeous piece as Dylan playing and singing alone at the piano is almost always special. This demo includes a number of lyrical variations from the released version, including a bridge that is not heard on Bob Dylan’s Greatest Hits Vol. II:

Sailin’ around the world in a dirty gondola
Sure wish i hadn’t sold my old victrola
Ain’t nothin’ like that good old rock ‘n’ rolla.

Besides the audacious only-Dylan-would-go-there rhymes, it’s a delightful conceit connecting the European sensibility represented by the gondola with old-timey music as symbolized by the victrola while also encompassing Dylan’s first love, true art, and calling as a rock ‘n roll star.

Knowing that the original performance of “When I Paint My Masterpiece” did not include a bridge and Dylan was writing to a piece of music already composed and recorded by Russell, the best guess is that this demo was recorded after the Blue Rock sessions.

The Band performed their own version of “When I Paint My Masterpiece” on 1971’s Cahoots:

Sung admirably by Levon Helm, the musical accompaniment includes a mandolin and Garth Hudson’s wonderful accordion, suitable instrumentation choices for the European sensibility of the lyrics. Speaking of lyrics, there are different variations in this version from Dylan’s demo as well as the Greatest Hits Vol. II version. For example, rather than “Botticelli’s niece,” Levon sings “pretty little girl from Greece” which suits his specific vocal delivery well. There’s also a lyrical change in the bridge as Levon sings:

Sailin’ around the world in a dirty gondola
Oh to be back in the land of Coca Cola!

This couplet simplifies the meter of the bridge from the demo’s slightly awkward rhythm and adds a wrinkle to the song not found in Greatest Hits Vol. II version: a longing for America. These lines allow Dylan to break out of the Old World sensibility of Europe. Robbie Robertson of The Band recently discussed how Dylan was inspired to write the bridge of “When I Paint My Masterpiece,” saying that it was after Robbie offered Dylan something to drink – “Do you want a Coke?” Add this anecdote to the Dylan legend, but, as with all of Robbie’s stories, we should accept it with a dump truck load of salt. Either way, it shows that Dylan was still playing with the song’s lyrical content even after recording it with Leon Russell in March 1971.

The Band closed out 1971 with a series of concerts at the Academy of Music in New York, concluding with a performance on New Year’s Eve. Dylan joined his old backing band onstage for the encore, which included a rendition of “When I Paint My Masterpiece.” It was included on the 2000 expanded edition of The Band’s peppy and refreshing live album Rock of Ages:

This performance comes only a few months after the recorded versions of both Dylan and The Band. The tempo here is slower, and, unfortunately, we don’t have Garth’s appropriate accordion. Instead, we are treated with his usual masterful organ playing along with Robbie replicating the mandolin part on electric guitar. We also get a taste of Rick Danko’s gorgeous harmony vocals with Dylan. Despite the lyrics’ supposed uncertainty about the timing of the next masterpiece, Dylan doesn’t seem worried as he sounds like he is having a ball playing and singing with his old pals.

Moving forward a few years, during the fall 1975 leg of the Rolling Thunder Revue, Dylan used “When I Paint My Masterpiece” as an opener of his set:

During this tour, Dylan sings the song as a duet with his old running mate Bob Neuwirth which may have contributed to the lyric switch from “You can almost think that you’re seeing double” to “You can almost think that you’re seeing your double.” Two old friends named Bob dueting, why not make that alteration? The song is a perfect selection for the Rolling Thunder Revue because the flexibility of the band’s instrumentation allows for a European flavor to the song’s presentation. Additionally, the lyrics depict scenes from a journey — “A plane ride so bumpy that I almost cried” and “Train wheels runnin’ through the back of my memory” — that resonate well with the traveling circus presentation of the Revue.

The Grateful Dead added “When I Paint My Masterpiece” into their regular repertoire in the late 80s as can be heard in this performance from March 29, 1990 at Nassau Coliseum in Uniondale, NY:

The Dead and their fans are road dogs so the touring aspect of the song certainly resonates, especially the words, “Oh the hours that I spent inside the coliseum.” Since they are playing in a coliseum, the line gets a roar of approval from the audience. The Dead certainly had to contend with “Dodging lions and wasting time” during their years on the road that it’s no wonder it became a favorite. Jerry Garcia’s ragged yet perfect harmonies and his nifty mid-song solo are highlights of the performance.

Dylan never left “When I Paint My Masterpiece” far behind in his own song rotation. Once during a concert in 1991, he said after performing the song:

“It’s my foreign language song! That’s what you asked for? All you art lovers out there!”

Like its sister song, Dylan included the song in the 2021 pandemic concert film called Shadow Kingdom: The Early Songs of Bob Dylan. He rewrote the lyrics to the song again, including these lines from the opening verse:

Oh, the streets of Rome are filled with rubble
Ancient footprints are everywhere
You can almost think that you’re seein’ double
On a cold dark night by the Spanish stairs
Got to hurry on back to my hotel room
Gonna wash my clothes, scrape off all of the grease
Gonna lock the doors and turn my back on the world for a while
Gonna stay right there ’til I paint my masterpiece.

With these new lines, Dylan doubles down on the painter references in the song, still playing with how to present the concept behind the song. Here he is at the age of 80 after writing hundreds of songs, receiving acknowledgements and awards from the media and peers, including the Nobel Prize of all things, still considering and contending with the external and self-imposed pressures of artistic creation. 

Many thanks to Jochen Markhorst for his assistance and contribution to this post.

Image: Sandro Botticelli, circa 1485, The Birth of Venus, tempera on canvas, Public domain, via Wikimedia Commons.