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The Andy Warhol Museum announces the public presentation of 10 rarely seen Andy Warhol "Screen Tests" on Times Square's electronic billboards from 11:57 p.m. to midnight each night in May 2015. The screenings are part of the ongoing project "Midnight Moment," a monthly presentation by The Times Square Advertising Coalition (TSAC) and Times Square Arts. Among the "Screen Tests" shown are those of Bob Dylan, Allen Ginsberg, Lou Reed, Harry Smith, and Edie Sedgwick.

Between 1964 and 1966, Warhol created almost 500 of these three-minute film portraits of famous and anonymous visitors to his studio, filming his subjects using a stationary Bolex camera loaded with 100-foot rolls of black and white 16mm film.

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Bob Dylan’s career as a painter is soured by the fact that many people first encountered his brushwork on the cover of his worst album, 1970’s Self Portrait; it features, appropriately, a self-portrait. His head appears to be floating in the pale blue ether and his nose and mouth are exaggerated blobs resting on his face. The lines are otherwise hard-edged and coarse, adding to the painting’s dubiously caricaturelike style, which borders on incompetence. The word “worst” is not used lightly.

In his 2004 autobiography, Chronicles, Mr. Dylan himself admitted, in so many words, how powerful a failure Self Portrait was. His description of recording the album could just as easily pass for an account of painting its cover: “I just threw everything I could think of at the wall and whatever stuck, released it, and then went back and scooped up everything that didn’t stick and released that too.”

Give a celebrity a canvas and you often end up with a disaster. Artwork by stars gives rise to a paradox: audiences would likely not care about the work if it hadn’t come from the hand of someone famous, but the final conclusion is typically “Don’t quit your day job.” As always, Mr. Dylan is a different kind of beast. His first exhibition of paintings in New York, “The Asia Series,” opened this week at the uptown branch of Gagosian, the largest gallery in the world. On view right now at Gagosian’s other locations are solo shows by the likes of Richard Serra, Andy Warhol, Dan Colen and Robert Rauschenberg. Mr. Dylan is no Rauschenberg, but the pairing of the singer with Gagosian makes sense, in a kind of Warholian sense of celebrity. It is a union of two men—roughly the same age—who are at a point in their careers where they can do anything they want with little risk to their reputations. Mr. Dylan can paint scenes, heavily influenced by Gauguin’s Tahiti works, of his misadventures in Japan, Korea, China and Vietnam that cast his subjects as radically other, and Larry Gagosian can show them.

Opium, for instance, which Mr. Dylan painted in 2009, is quite simply perverse. A young woman lounges in a cluttered bedroom, eyes shut in a loopy opiate haze. Scattered about the scene are a fan, a vase with what appears to be bamboo, containers of makeup and a large pipe. The woman rests angelically, framed in a come-hither pose that is directed entirely at the male artist. The Gagosian exhibition is being touted as “a visual journal of his travels” and comprises “firsthand depictions of people, street scenes, architecture and landscape.” Presumably, Mr. Dylan was in this opium den, gazing at this young woman, approaching her but never arriving for the sake of his art. Whether or not that is true does not matter. For years, people believed Mr. Dylan grew up in a traveling circus and hoboed his way across the country in freight train boxcars because he lied to a publicist at Columbia Records back in the ’60s.

Perversity and possible inauthenticity aside, Opium is not a bad painting, but one wonders how much of its interest rests on the person making it rather than on the quality of the work itself. It is not just a depiction of a young woman on drugs, it is a depiction of a young woman on drugs made by the man who wrote “Like a Rolling Stone.” It is all the more tempting to draw connections between Mr. Dylan the singer and Mr. Dylan the painter because the styles overlap—he is, at once, effortless and portentous. Opium showcases the same strange interplay of universality and narcissism that is also at stake in much of his music, especially the later songs. The oversexualized image recalls the opening line of Mr. Dylan’s 2006 Modern Times album, a line so specifically about Mr. Dylan himself that it somehow taps into an identifiable desire: “I was thinking ’bout Alicia Keys/I couldn’t keep from crying/she was born in Hell’s Kitchen/I was living down the line.” Few people could get away with such a lyric. No matter what one thinks of Alicia Keys, he manages to turn the humorous sexual pining of a dirty old man into a gloomy commentary on the inevitability of age and impotency. But would we care if that line was sung by, say, Paul Simon? Looking at his artwork, it is hard not to consider the very real possibility that we forgive Mr. Dylan a certain level of mediocrity because when he is good he is so much better than anyone else.

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