All Superstars Should Take Under the Cherry Moon-Sized Risks

All Superstars Should Take Under the Cherry Moon-Sized Risks
Image:Warner Bros. Pictures

Once upon a time, referring to a piece of mainstream art as a “vanity project” was a common dismissal. It may be hard to imagine the sting of such a critique now, when concocting, investing in, and selling identity is a viable career path to which many openly aspire. Vanity has become a project in and of itself.

But for better or worse, in the ‘80s, the idea of a pop star openly cultivating the cult of their personality could be interpreted as distasteful. Prince’s directorial debut, Under the Cherry Moon, was received as such—when it was received at all—after it hit theaters with a thud in the summer of 1986. The black-and-white musical melodramedy flop perhaps wouldn’t have been such a disappointment if it weren’t following Purple Rain, a movie-music one-two punch that sent Prince flying into the stratosphere just two years earlier. The critics consensus summary on Under the Cherry Moon’s Rotten Tomatoes page says it all: “Under the Cherry Moon may satisfy the most rabid Prince fans, but everyone else will be better served with this vanity project’s far superior soundtrack.”

Or does it? Labeling Under the Cherry Moon a vanity project implies that it existed as a thinly veiled excuse for Prince to jump in front of cameras. Now, jumping in front of cameras is one of the things that stars tend to do, so it hardly seems fair to admonish a pop star for using his image in an attempt to entertain. That’s like criticizing a duck for quacking or bats for hanging upside down (even in a restaurant, as they do in Under the Cherry Moon, as an absurd scene-ending device). Regardless, Under the Cherry Moon was no empty gesture. It allowed allowed audiences to see a smilier, sillier side of Prince, a self-styled enigma who had been cultivating mystique through his duration in the spotlight. He was practically a remote island of a man by 1986, refusing interviews and, for his preceding album, 1985’s Around the World in a Day, eschewing virtually all promotion. In the opening scene, in which his gigolo character Christopher Tracy plays piano and makes eyes with a mutually admiring woman at a bar, a Rudolph Valentino-channeling Prince expresses more with his face than his reliably cool countenance had allowed in public up to that point—perhaps cumulatively.

Image:Warner Bros. Pictures

Under the Cherry Moon found Prince at his most talkative and least understood (at that point, anyway). But the film was more than just a way to fill some blank spots in the persona Prince had been sketching. The plot concerns the attempt made by Christopher and his sidekick Tricky (Jerome Benton) to woo an heiress named Mary (Kristin Scott Thomas in her big-screen debut) who’s worth millions. It takes place on the French Riviera, and as a pair of happy-go-lucky hustlers, Christopher and Tricky surf a sea of white people for the seeming sheer exhilaration of it. The rich white people are often portrayed as unconsciously ridiculous and reflexively wack, like when Mary’s birthday-party drum solo encourages a rather prim and proper chanting of, “Planet rock, you just can’t stop,” by the crowd.

While Prince rolled his eyes at the melanin-deprived status quo, race was a subject right on the tip of Becky Johnston’s screenplay. Instead of an explicit interrogation or obvious monologuing on the subject, it’s mostly referred to with subtlety as a facet of Christopher and Tricky’s lived experience. The score-settling in Christopher’s pledge to Mary’s disapproving father—“You rich folks always take from people like me. That says what? That says now I’m gonna take something from you.”—is about as close to overt race commentary as Under the Cherry Moon gets (it’s also indicative of Prince’s tendency to treat women as objects in the public sphere). Otherwise, Under the Cherry Moon is content to show instead of telling, and this is most apparent in the “Wrecka Stow” scene, probably the most beloved moment in the film, in which Christopher and Tricky crack up over Mary’s inability to grasp African American Vernacular English.

Prince was a proud Gemini, who again and again throughout his career, explored simultaneous duality. There was Camille, his pitched-up alter ego who was maybe a female alter ego, maybe a manifestation of evil (maybe both!). His take on Batman lore involved him inhabiting a half-Batman/half-Joker character named Gemini. In Under the Cherry Moon, the opposing forces in one human vessel explored are those of the love of love and the love of money. The film could never be mistaken as a dissertation on sex work, but by making Christopher a gigolo, the film is able to explore the inextricable binding of love and sex in such a lifestyle. (This made explicit in the song “♥ Or $,” which plays during the Under the Cherry Moon, but instead of appearing on its soundtrack album, Parade, showed up as the b-side of the “Kiss” single.) Is Christopher’s love for Mary real? Could it ever be considered as such when he entered their relationship with designs on her fortune? Under the Cherry Moon doesn’t offer much by way of definitive conclusions on such matters, but unlike a lot of movies at the time (particularly those which have gone down as notoriously bad cinema), it has philosophical ideas about this stuff and is unafraid to pose questions.

Ambiguous duality also notably shows up in the relationship between Christopher and Tricky, two best friends who live together and share several homoerotic moments. Christopher and Tricky are so close as to openly flirt with queerness, and the overall effect is to display intimacy among ostensibly straight men. I don’t believe that representation is more of an end than a means, but it was simply revolutionary to unabashedly portray this sort of intimacy (particularly among two Black men) and to take its implications seriously while joking all the while.

Mostly inspired by ‘40s musical comedies (like those starring Fred Astaire) but in a contemporary setting, Under the Cherry Moon is both a joke and serious. I think that it’s unfair to dismiss it as only a “vanity project,” but the label wasn’t entirely off the mark either. The film is a showcase for Prince’s ego, which by the time of filming in late 1985, had ballooned considerably, according to those around him. In Alan Light’s Let’s Go Crazy: Prince and the Making of Purple Rain, Revolution member Lisa Coleman said that after the legacy-defining success of Purple Rain, Prince’s ego inflated and he “could just get mean” at times. “He was pretty confident about everything—almost too cocky, in a lot of ways, and he kind of burst the bubble a little bit,” his former bandmate recalled. “Like, ‘I can do anything,’ ‘Muthafuckas will buy anything.’” Watching Prince strut around on screen as though he was on a car lot and had enough cash in his pocket to drop on a Rolls right then and there, you get the feeling that even within its highly stylized world, Under the Cherry Moon is something of legitimate, honest expression.

There’s also the matter of his employment of Benton as his sidekick. Benton was initially Time lead singer Morris Day’s sidekick—he’s the guy who held up the mirror Day used to check himself out onstage, a trademark move. In Day’s you-have-to-read-it-to-believe-it 2019 memoir On Time, he wrote that he believed Christopher was based on the persona previously embodied by Day (a Prince creation—the Time was initially a Prince side project voiced by Day and a song on the act’s second album written by Prince was called “Gigolos Get Lonely Too”). Regarding the products of Prince’s theft, Day, who frequently addresses Prince’s hypothetical response to what Day just said so that much of it is written in the second person, writes:

With Purple Rain you’d had partial control. Its success gave you the confidence to take total control of Cherry Moon. You were gutsy. You were thinking, “Why shoot another movie in freezing-ass Minneapolis? Why not go to the south of France? Why not shoot it on the Riviera, the most glamorous spot in Europe? And why not make myself up to look like Rudolph Valentino?”
There’s a resemblance between you and Rudolph, I admit, but casting yourself as a gigolo hitting on European honeys got boring. Also got boring watching you go for the comedy routines I did with Jerome. I heard you saying, “I don’t need MD. I can do what MD did—and then some.”

Prince famously stole “Kiss,” as well. Originally an acoustic blues number that he gave to protege band Mazarati, when he heard the band’s skeletally funky arrangement of the song he took it back, deeming it “too good” for the band. The song went on to become his third No. 1 on the Billboard Hot 100 and one of the artist’s signatures.

Shady as this behavior may have been, none of it makes me appreciate Prince the artist less—it makes me understand Prince the person more. Funny how a project frequently lambasted for indulging Prince’s ego reveals so much about his humanity.

Under the Cherry Moon is hardly perfect. Its plot is so threadbare that its accoutrements are more impressive than its actual shape. The vintage look of the picture does not serve the giddily bizarre (and often kaleidoscopically sunny) funk-pop concoctions that Prince and the Revolution whipped up on Parade (some days, my favorite Prince album). It’s just too easy to get distracted by the musical brilliance. But has it aged well? I’d say so. A number of positive reappraisals have been published in the time since Prince’s 2016 death in outlets such as and Film Comment. It’s easier than ever to see what Prince was going for and ignore the bullshit, a process literalized in the meme-ification of some of the movie’s more striking visual moments, such as this one:

Image:Warner Bros. Pictures

Even if it’s just in seconds-long bits, Under the Cherry Moon lives on, which is more than you can say about most notorious flops.

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