The Purple Rain Tour was the Eras Tour of the 80s, the hottest concert ticket in the world. Between 1984 and 1985, Prince played sold-out shows for 1.7 million people in 34 cities across North America. Then just 26 years old, the Purple One had not only a Top 10 album with Purple Rain but also one of 1984’s highest-grossing films—his semi-autobiographical musical of the same name, which would win him an Academy Award for best original song score.

It came as a surprise to some, in a year dominated by mainstream blockbusters such as Ghostbusters and Indiana Jones and the Temple of Doom, that a musical about a defiantly androgynous, hypersexual young Black man who dressed like an 18th-century nobleman—with his kohl-rimmed eyes, tight patterned suits, and ruffly shirts—could achieve such resounding success. Studio executives at Warner Bros., doubtful of its chances, had asked if Prince would agree to being replaced by John Travolta in the lead role, but Prince rejected that idea.

Prince performs at Wembley Arena during the London stop of his Parade Tour, 1986.

As he crisscrossed the country on his Purple Rain tour bus, literally riding high, Prince liked to watch classic films on TV to unwind. He had always been a movie buff, and was especially a fan of Old Hollywood. “I sat with him on the bus and we would watch Humphrey Bogart and Bette Davis movies,” says Jerome “Tricky” Benton, a backup dancer on the Purple Rain Tour and Prince’s close friend from the beginning of his career in Minneapolis.

“Then Prince started coming up with this idea. He said, ‘We’re gonna do a movie and we’re gonna make it in black-and-white, and we’re gonna do it in France.’ He said, ‘We’re gonna start writing it.’ And I said, ‘Write a movie? I ain’t never written no movie.’” (Benton, now a writer, actor, and producer, was 22 at the time.) It almost sounds like it could have been dialogue between Prince’s and Benton’s characters in Under the Cherry Moon (1986), Prince’s second film and his directorial debut.

Prince wanted the relationship of the film’s two male leads to be like the funny, easy rapport he had with his buddy Benton in real life. In Under the Cherry Moon, they play a couple of grifters in the South of France who plan to scam a beautiful heiress—played by a 25-year-old Kristin Scott Thomas in her first feature film—until Prince’s character falls in love with her. Benton says, “Prince made me watch Some Like It Hot,” a 1959 black-and-white movie starring Marilyn Monroe in which Tony Curtis and Jack Lemmon play a couple of down-and-out jazz musicians on the run. “He made me do my homework.”

“Then Prince started coming up with this idea. He said, ‘We’re gonna do a movie and we’re gonna make it in black-and-white, and we’re gonna do it in France.’”

Under the Cherry Moon is a movie about movies; it’s a riff on the sort of frothy screwball comedies directed by Ernst Lubitsch and Preston Sturges. Its plot resembles the storylines of any number of films from the 1930s about rebellious heiresses who get into hot water with their controlling fathers when they fall for men considered to be beneath them (It Happened One Night and My Man Godfrey among them).

But while movies that pay homage to Hollywood’s golden age had been done before, Prince’s film is a more radical work that turns the screwball-comedy paradigm on its head—starting by casting a gender-bending, self-styled sexy motherfucker who happens to be Black as its romantic lead. “Prince always knew exactly what he was doing,” says Benton.

Jerome “Tricky” Benton, Prince’s friend and a backup dancer on the Purple Rain Tour, in Under the Cherry Moon.

It’s striking now to see how reviews of Under the Cherry Moon—almost all of them scathing; the Los Angeles Times called it “a dismal flop”—never mention race. This despite the fact that a major element of the plot involves the hatred directed at Prince’s character by the father of the white woman he’s secretly been seeing, an evil bastard played by that master of evil bastards, the British actor Steven Berkoff (who played the villains in Beverly Hills Cop and Octopussy).

In Under the Cherry Moon, Berkoff’s character is so filled with hate that he has Prince’s character killed—something you never saw happen to Clark Gable or Cary Grant in their romantic roles. But it was something that happened to thousands of Black men in America when they showed an interest in white women, and when they didn’t. What the critics missed is that Under the Cherry Moon isn’t just about race; it’s about white supremacy in Old Hollywood, which never cast men who looked like Prince as romantic heroes.

In the film, Prince plays a grifter who plans to scam a beautiful heiress until he falls in love with her.

I became a Prince fan in the 80s, but always avoided watching Under the Cherry Moon—I guess because I didn’t want to witness Prince’s biggest failure, according to critics. Gene Siskel, on his and Roger Ebert’s weekly TV show, At the Movies, said Under the Cherry Moon “insults our intelligence.” Ebert asked, exasperated, “What’s [Prince] doing in the South of France?” As if a place that fancy was not a fitting setting for someone like Prince—an attitude that exemplifies what Under the Cherry Moon is actually about.

The film received five Golden Raspberry Awards, including worst picture, worst director, and worst actor, for Prince. But when I finally streamed it, for a moment I wasn’t sure if I was having a flashback to a highly enjoyable trip. Under the Cherry Moon is a kind of wild Prince fever dream, a sumptuous, stylish production burning with the beauty of the South of France in almost every frame, full of stunning people, sets, and clothes by the French costume designer Marie France (given her start by Prince, with Purple Rain).

“It looks fabulous,” said France—who didn’t even like the film, in which she dressed Prince in a series of outrageously sexy looks: glossy tuxes, beaded jackets, crop tops and toreador pants, bejeweled turbans, and a very special white shoulder-padded duster made of the same cashmere used by the tailors who make religious garments for the Pope. As usual, Prince was crossing boundaries, daring anyone to say that a leading man couldn’t dress like a drag queen, or however he wanted.

Under the Cherry Moon was shot in color and later converted to black-and-white.

At the insistence of Warner Bros., Under the Cherry Moon was shot in color by the late German cinematographer Michael Ballhaus, who had worked with Martin Scorsese and Rainer Werner Fassbinder; later, the film was converted to black-and-white for the classic Hollywood look that Prince had originally envisioned and which the studio feared would render it commercially unviable. (While I understand what he was doing, you almost wish you could see the film in color, if only for the lush production design of Richard Sylbert, who had just won an Academy Award for 1984’s The Cotton Club.)

How did Prince ever get anybody to let him make this movie?, I wondered as I watched. It felt so ahead of its time, camp and weird in the best way possible.

“Prince always knew exactly what he was doing.”

“Mind you, we were just coming off a big hit with Purple Rain,” Benton says. The film had grossed nearly $70 million worldwide—around $200 million in today’s dollars—against a $7.2 million budget, so the studio was optimistic that Prince was going to work his magic again with Under the Cherry Moon, and gave him something close to carte blanche to do it. In 1985, Prince’s then management team—Robert Cavallo, Joseph Ruffalo, and Steven Fargnoli, who had also produced Purple Rain (and with whom Prince later had a very public falling-out)—secured a budget of $12 million, around $33 million today. Without a script.

A 25-year-old Kristin Scott Thomas on set. Under the Cherry Moon was her first feature film.

Prince was a believer in young talent, so the producers agreed to hire an inexperienced screenwriter, Becky Johnston, based on a test screenplay she’d written. (Johnston went on to receive an Academy Award nomination for best adapted screenplay, for 1991’s The Prince of Tides.) Prince’s own notes on the film—which he’d recorded in longhand in a blue spiral Mead notebook—laid the groundwork for the story.

In these pages you can also see the dialogue for one of the film’s best-known scenes, in which Prince’s and Benton’s characters tease Kristin Scott Thomas’s character for essentially being so white that she can’t catch on to the fact that they’re talking about a place where records are sold when they say “the wrecka stow.” Here, Prince is turning the tables again, with the Black characters laughing at the white one instead of the other way around, as was so often seen in racist films from Old Hollywood where Black actors were used as comic relief.

Prince wanted the relationship of the film’s two male leads to be like the funny, easy rapport he had with Benton in real life.

In June of 1985, a couple of months after the Purple Rain Tour ended, Prince, Fargnoli, and a few others went to France to scout locations. Prince decided that he wanted to shoot Under the Cherry Moon primarily in Nice and St. Tropez, as well as at Les Salons de la Rotonde, a glittering 1904 salon in Beaulieu-sur-Mer.

Prince’s management rented a château in the hills above Nice, belonging to celebrity novelist Jackie Collins, as a place for him and his entourage to stay during filming. “We’d ride scooters down the hills to town,” remembers Benton. “Or we’d be riding around in a big ol’ American limousine that takes 10 minutes to turn a corner. All of it was glamorous—the clothes, the cars, the people.”

“I remember we were doing a scene at one of those big beachfront houses with a garden,” says Steven Berkoff, who took over for Terrence Stamp after Stamp quit early in the production for undisclosed reasons. “I was sitting on the terrace with Alexandra Stewart”—the Canadian actress and longtime partner of Louis Malle, who played Berkoff’s wife in the film—“and I suddenly thought, Here I am on this gorgeous, sunny day in one of the most beautiful seaside cities in the world, being directed by Prince. And I had to pinch myself to make sure this was all real. I had that feeling quite a few times on this film. It was absolutely the most glamorous experience.”

In September of 1985, 16 days into filming, Prince took over from the original director, Mary Lambert, then known for directing music videos for Prince and Madonna (and now as a TV director and singer-songwriter); Prince never discussed their differences. He had first asked Scorsese to direct, but Scorsese declined, reportedly joking, “There can’t be two geniuses on set.”

The film is a kind of wild Prince fever dream, a sumptuous production burning with the beauty of the South of France.

“When Prince started directing, it was nothing new,” Benton says. “We’d done videos with Prince; we’d taken direction from him at band rehearsals. He made an amazing leader.”

“He was a very precise director,” says Berkoff, “because he came from music, where you have to get the notes just right. I remember I was doing a scene with Kristin Scott Thomas where I was chastising her, warning her not to see this man, and we hear ‘Cut!’ and the next sound we hear is this tapping as Prince comes down the corridor, having watched the scene on a monitor in another room. It was the sound of his high heels. I’d hear this tap-tap-tap-tap after every scene and I could always tell, depending on the rapidity of the tapping, what kind of notes he was going to give.”

Because Prince was a perfectionist, and because he wanted to be taken seriously as a director, there wasn’t a lot of partying during the shoot, according to Benton. “Or let’s just say it was low-key,” he says. “Prince knew he needed to protect himself and his people. But, sure, we had parties—great parties—they just weren’t wild, crazy parties. We partied with Prince Rainier and Adnan Khashoggi, the biggest arms dealer in the world. We were floating around on the weekends on 100-plus-foot yachts.”

Some of that partying was to songs from Parade, the soundtrack of Under the Cherry Moon, which was called a masterpiece by some at the time of its release, a few months before the film’s premiere. “Nobody would guess it was a soundtrack for a (sub-par) film,” side-eyed The Guardian. The album’s moody mix of pop, rock, jazz, and funk—which included the mega-hit “Kiss”—was a departure for Prince, who was always re-inventing himself musically.

Thomas and Prince in a scene from the film.

Prince never saw Under the Cherry Moon as a musical, though in it he does perform two songs: “Girls & Boys” and “Mountains,” which he sings “from heaven” as the outro. “Love will conquer if you just believe (oh yeah!),” he sings, interjecting a note of hope after his character is murdered.

“I remember I was doing a scene with Kristin Scott Thomas … and we hear ‘Cut!’ and the next sound we hear is this tapping as Prince comes down the corridor.... It was the sound of his high heels.”

Before filming got under way, Prince had also replaced his leading lady, his then girlfriend, Susannah Melvoin (who was the sister of his bandmate, guitarist Lisa Melvoin). Kristin Scott Thomas, then in France performing in a play, was called in to audition for a smaller role and snagged the lead, which so surprised her she later described it as “an out-of-body experience.” Prince’s interest in Thomas was piqued when she started ad-libbing in character at a dinner on the night of her audition, Benton says. “We were talking, laughing, drinking wine, and we started conjuring up some dialogue Prince liked—that and her amazing presence.”

“The whole thing was just a miracle,” Thomas said on The Graham Norton Show in 2021. “That was the summer of Around the World in a Day”—Prince’s 1985 album, featuring “Raspberry Beret”—“and I had been listening to it over and over on my Walkman … and [after the audition] they said, can you come back at six to meet Prince? And I had to keep reminding myself that this was real.”

While paying homage to Hollywood’s golden age, Under the Cherry Moon also turned the screwball-comedy paradigm on its head.

“I brought my mother to the premiere,” Thomas went on, “and [afterward] Mummy … patted my knee and said, ‘Don’t worry, darling, it’ll be better next time.’” Thomas was nominated for two Golden Raspberries for her work in Under the Cherry Moon, for worst supporting actress and worst new star, which seems crazy when you watch her arresting, fiery performance. (She would later be nominated for an Academy Award for best actress, for 1996’s The English Patient, among many other accolades throughout her career.)

But clearly, Under the Cherry Moon wasn’t for everybody—including some of the citizens of Sheridan, Wyoming, the small, mostly white cowboy town that hosted the premiere. Sheridan was picked as the unlikely spot for the event after one of its residents, a 20-year-old hotel worker named Lisa Barber—a Prince fan who had seen Purple Rain 13 times—was the lucky 10,000th caller in an MTV competition called “Win a Date with Prince.”

Prince and super-fan Lisa Barber arrive at the premiere of Under the Cherry Moon.

“While the Centennial Theater audience cheered Prince on in several scenes, there didn’t seem to be overwhelming enthusiasm for the film itself,” sniffed the Los Angeles Times. Prince already seemed to know at the premiere that Under the Cherry Moon was in trouble, but he just shrugged and smiled and, putting his arm around Barber, said, “I got a cute date.”

Though an estimated two million people watched that premiere live on MTV, Under the Cherry Moon lost money at the box office, earning just over $10 million. Was Prince upset about the terrible reviews? “Prince never cared what people said,” says Benton. “Think people wanted to change Mona Lisa’s smile? He wrote in his song [“D.M.S.R.”], ‘I don’t care to win awards.’ Prince was confidence. Prince was Prince. And nothing could touch that.”

Under the Cherry Moon is available for streaming on Amazon Prime Video and Apple TV+

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Nancy Jo Sales is a journalist whose 2010 article for Vanity Fair “The Suspects Wore Louboutins” inspired the Sofia Coppola film The Bling Ring. She is the author of American Girls: Social Media and the Secret Lives of Teenagers and Nothing Personal: My Secret Life in the Dating App Inferno