Prince's 1987 double-LP Sign O' the Times is undeniably a masterpiece and arguably the best album he ever released. Below you'll read the stories behind all of its songs and two B-sides, as well as links to our longer pieces about each of the tracks.

1. "Sign O' the Times"

The title track from Sign O' the Times, the album's first single, is one of his strongest pieces of social commentary. He updates Marvin Gaye's "What's Going On," Stevie Wonder's "Living for the City" and his own "America" in depicting the bleak state of urban life — AIDS, drugs and gangs — as the country entered the late '80s. But where Prince would have previously advised partying the troubles away, here he suggests finding love and starting a family as the cure.

Read the full story: Prince Pushes Back Against Societal Ills on "Sign O' the Times"

 

2. "Play in the Sunshine"

After the bitter pill of "Sign O' the Times," Prince offers the spoonful of sugar in "Play in the Sunshine." The song breaks through the bleakness of the opener with a jolt of ecstasy — although not the drug, for which he has no use — that evokes "Let's Go Crazy" both in spirit and tone.

Read the full story: Prince Makes a Joyful Noise in "Play in the Sunshine"

 

3. "Housequake"

"Housequake" is the first glimpse we get of Camille, the alter ego he created by speeding up his vocals to sound more like a woman. Four of the tracks on Sign O' the Times, along with the B-side "Shockadelica," are sung in the voice of that character, for whom he had recorded an entire album that was eventually scrapped. (All the tracks did eventually wind up seeing the light of day in some fashion.)

Read the full story: After Firing the Revolution, Prince Starts a One-Man "Housequake"

 

4. "The Ballad of Dorothy Parker"

Prince opened up his home studio on Galpin Blvd. in Chanhassen, Minn., by recording "The Ballad of Dorothy Parker." Although there was a technical problem with the new console that removed the high-end, Prince kept on creating through one of his typical 24-hour recording sessions until it was completed, at which point engineer Susan Rogers was able to address the glitch. Rather than redo the song, Prince kept it as is.

Read the full story: Happy Accidents Abound in 'The Ballad of Dorothy Parker"

 

5. "It"

For a guy who famously didn't have any problem using sexually explicit language for much of his career, Prince stuck with the colloquial "it" here, even though he was as horny as ever. "It" also forms one of the highlights Sign ‘O’ The Times: The Motion Picture, where the song comprised a medley with "Forever in My Life," unleashing a funky workout that even saw Dr. Fink come out from behind his keyboards.

Read the full story: Prince Admits He Thinks About "It" All the Time

 

6. "Starfish and Coffee"

"Starfish and Coffee" was based on a story that Susannah Melvoin, then Prince's fiancee, told him about a girl she knew in grade school who told colorful tales, including that her breakfast consisted of "starfish and pee pee." Prince removed the urine and replaced it with the similar sounding "coffee" and gave Melvoin a co-writing credit.

Read the full story: Prince Turns a Young Girl's Images Into "Starfish and Coffee"

 

7. "Slow Love"

Sign O' the Times' other co-write is "Slow Love," composed with his friend Carole R. Davis. The lyrics here take a back seat to the work by the horn section of saxophonist Eric Leeds and trumpet player Matt “Atlanta Bliss” Blistan. “He’d sing [the parts] to us,” Blistan said. “It was just incredible to be with him and see the creativity sparking just right there.”

Read the full story: Prince Makes "Slow Love" With Carole R. Davis

 

8. "Hot Thing"

Leeds again is given a spotlight on "Hot Thing," blowing his sax over a techno groove. While the song, a No. 14 hit in the U.S., contains plenty of his trademark come-ons, lyrics like "are your smiles for me?" hint at some of the romantic discord between he and Melvoin that would work its way into other songs.

Read the full story: Prince's Sharp, Minimalistic "Hot Thing" Provides Needed Release

 

9. "Forever in My Life"

As with "The Ballad of Dorothy Parker," one of the unique elements of "Forever in My Life" came about by mistake. Rogers placed the background vocals before the lead vocal instead of directly underneath it. But Prince liked the result, and it stayed in the final version.

Read the full story: Prince Makes the Silly Love Song Cool on "Forever in My Life"

 

10. "U Got the Look"

Camille returns for "U Got the Look," a duet with Sheena Easton. But the Scottish singer didn't realize what she was in for when she agreed to record with him. "He said, 'Do you want to just come in and sing some backup vocals on the choruses?'" Easton recalled in 2012. "So, I went into the studio, and because I didn't know I was singing against him, I was all over the place – and he said he kind of liked that, so he expanded it into a duet."

Read the full story: Sheena Easton and Prince Hit a High Point With "U Got the Look"

 

11. "If I Was Your Girlfriend"

"If I Was Your Girlfriend," with its sophisticated, subtle lyrics and the gender-bending of Camille, became Prince's lowest-charting single since the Controversy era, reaching only No. 67. That said, it's the most sensuous song on Sign O' the Times, with Prince exhibiting a rare degree of vulnerability.

Read the full story: When Prince Got Deliriously Weird on "If I Was Your Girlfriend"

 

12. "Strange Relationship"

Prince's famed work ethic meant that he didn't often have to reach back into his past for material, but he did with "Strange Relationship." The song was written in 1983, reportedly after he caught Denise "Vanity" Matthews cheating on him. He revived it in 1985 with Wendy & Lisa for the Dream Factory project and reworked it for Sign O' the Times, removing or mixing down their contributions and putting it in the voice of Camille.

Read the full story: The Long, Strange Trip of Prince's "Strange Relationship"

 

13. "I Could Never Take the Place of Your Man"

The fourth and final single from Sign O' the Times, "I Could Never Take the Place of Your Man" features Prince in a rare mindset: turning down the possibility of sex because he realizes that she needs more than just a one-night stand. As with "Strange Relationship," the song wasn't written for the album, with Prince first recording it in 1982.

Read the full story: Prince Goes Full-On Power Pop With "I Could Never Take the Place of Your Man"

 

14. "The Cross"

In an album filled with carnal delights, Prince delivers the sacred towards the end, reminding us of Jesus Christ's sacrifice. After the singer's conversion to Jehovah's Witnesses, he changed the lyric to "The Christ" because his faith told him that Jesus was crucified on a single stake, as opposed to the commonly taught two-beam cross.

Read the full story: When Prince Preached Redemption on "The Cross"

 

15. "It's Gonna Be a Beautiful Night"

Unlike every other song on Sign O' the Times, "It's Gonna Be a Beautiful Night" didn't begin in the studio, but rather during a show at Le Zenith in Paris in the summer of 1986. Prince took the recording and overdubbed horns, a sample of "The March of the Winkies" from The Wizard of Oz and Sheila E. rapping the Edward Lear poem "The Table and the Chair" over the phone.

 

16. "Adore"

On Sign O' the Times' closer, Prince draws blurs the line between the sacred and profane, with the six-and-a-half-minute slow jam showcasing his gospel-inflected falsetto vocal. Although it was never commercially released as a single, it received considerable urban radio airplay, drawing upon both the "quiet storm" genre of adult contemporary R&B as well as the classic Memphis soul of Al Green.

Read the full story: "Adore" Is the Love Song to End All Love Songs

 

17. "La, La, La, He, He, Hee"

The B-side to "Sign O' the Times" was another collaboration with Easton. But unlike her vocal-only contribution to "U Got the Look," she earned a co-writing credit thanks to her (admittedly silly) lyric additions to "La, La, La, He, He, Hee." "See, I have six cats. It was about a cat up in a tree teasing a dog," she said. "I was actually being sarcastic. He said, 'Yeah, that could be a song,' and I was like 'Oh yeah, like what do you want me to sing? La La La, He He He — I love you, you love me? That's how talented I am?'" Prince told her to write exactly that.

Read the full story: Prince and Sheena Easton Get Funky Silly on "La, La, La, He, He, Hee"

 

18. "Shockadelica"

Prince wrote "Shockadelica" for a solo album of the same name by former Time guitarist Jesse Johnson. But Johnson declined the track because he wanted to forge an identity of his own, so Prince told Johnson that he would put it out himself, thereby claiming the titular word for himself in the public's imagination. It wound up as the B-side to "If I Was Your Girlfriend" and was later transformed by Ween into "L.M.L.Y.P.," which brought the song into more sexually explicit territory.

Read the full story: The Strange, Three-Sided History of "Shockadelica"

 

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