When you reach the kind of dizzying aesthetic heights that would leave other artists happy to rest on their laurels but continue to challenge (and sometimes even top) yourself, you’re working on a Prince-like level. While the jury is still out as far as to whether or not Prince actually originated on this planet (he was ostensibly born in Minneapolis in 1958), most normal human beings would've probably been happy to ride the mega-success of an album like 1984's Purple Rain throughout the entirety of their career, that certainly wasn't the case here. He just kept on pushing every envelope he saw.

Less than a year after ascending to the peak of pop culture with multi-platinum Purple Rain (the soundtrack to his debut film of the same name), Prince touched on the realm of psychedelic pop in 1985 with the trippy Around the World in a Day. While the album didn't achieve the rampant success of Purple Rain, it helped establish that we should expect the unexpected from Prince. And the following year, he upped the ante again with another multimedia project: his second movieUnder the Cherry Moon, and its soundtrack, Parade.

In the film (the musician's directorial debut), Prince plays a gigolo who falls in love with the wealthy heiress he was trying to swindle. But where the movie Purple Rain was a bold cinematic statement full of verve and vitality, Under the Cherry Moon was decidedly not. Is the storyline reflected in the songs? Possibly. But (as the trailer below proves) it's probably better if you separate the movie from the music and enjoy Parade as a standalone album.

Despite Prince’s reputation for being a multi-talented control freak who prefers playing most of the instruments on his albums, he collaborated with one man whose contributions were crucial to the creation of Parade and the evolutionary step it represented. Jazz arranger Clare Fischer had been crafting arrangements for jazz, latin and R&B albums since the ‘50s, and his idiosyncratic style informs Parade more profoundly than anyone other than Prince.

Although Prince had never worked with a full orchestra before, Fischer’s presence is immediately felt with Parade's opener, “Christopher Tracy’s Parade,” named for the lead character Prince plays in the movie. Fischer's jazz orchestrations create a kaleidoscopic, slightly disorienting feel with a whirling panoply of tonal colors and bold use of avant-garde harmonies. The jazzy arrangements also transform the funky R&B grooves of songs like “I Wonder” and “Life Can Be So Nice” into something stranger, providing the perfect framework for the lush, piano-based jazz instrumental “Venus de Milo.” And when Prince ventures into a French-flavored café jazz stroll complete with fluttering accordion on “Do U Lie,” Fischer’s orchestrations are there to lend just the right continental touch. But this is still a Prince album, after all, and the lean, modernist funk of “New Position” and “Girls & Boys” drives that point home.

Then, of course, there’s “Kiss" – one of Prince’s greatest achievements. Funky, funny and presumably the only tune in his catalog to be covered by both Tom Jones and an animated penguin with the voice of Nicole Kidman, the song reached No. 1 on the Billboard Hot 100 in 1986 and, almost by its inclusion alone, made Parade a must-own album.

Fortunately, "Kiss" was far from the only innovative music on Parade. Even in the wake of Purple Rain and Around the World in a Day, the album traverses a thrilling variety of moods and modes from the spare, jazz-inflected bittersweetness of “Under the Cherry Moon” to the jubilant R&B explosiveness of “Mountains” and beyond.

And the album closes with its most unexpected stylistic leap of all: “Sometimes It Snows in April." Written with Wendy Melvoin and Lisa Coleman of his band, the Revolution, the song is a delicate, ethereal, folk-jazz ballad with a core of acoustic guitar and piano. The dreamy feel, sophistication and vulnerability underline the strong Joni Mitchell influence that Prince would eventually cop to. The song also reintroduces his character from Under the Cherry Moon, making for a nice conceptual bookend to the album’s opening cut. But even if you don’t give a rat’s posterior about the exploits of Prince's fictional gigolo, you’d be doing yourself a disservice if you never took part in his parade.

Prince’s Bandmates: Where Are They Now?

More From Ultimate Prince