1987年，Prince发行了又一张具有轰动效应的经典专辑《Sign o' the Times》，这张专辑在商业和评论界都再次获得了巨大的成功，从这张专辑里诞生出了《I Could Never Take The Place of Your Man》《If I Was Your Girlfriend》《U Got The Look》等经典的冠军单曲。虽然在这张专辑的音乐风格上，Prince没有再次做出什么令人大跌眼镜的举动，但这次在歌词创作方面却颇为闪光。尽管整张专辑的主题内容是性以及其他一些相对消极的内容，但是这张专辑里的多首单曲以及其紧凑的歌词内容，也再次让人们为Prince的创作才华感到由衷的赞叹。在这张非常成功的专辑发行之后，Prince的变得更为野心勃勃，不过这种野心勃勃却让他开始和唱片公司发生了矛盾。

这张专辑在滚石杂志选出的500张历代最强专辑中排名第93位。

Fearless, eclectic, and defiantly messy, Prince's Sign 'O' the Times falls into the tradition of tremendous, chaotic double albums like The Beatles, Exile on Main St., and London Calling -- albums that are fantastic because of their overreach, their great sprawl. Prince shows nearly all of his cards here, from bare-bones electro-funk and smooth soul to pseudo-psychedelic pop and crunching hard rock, touching on gospel, blues, and folk along the way. This was the first album Prince recorded without the Revolution since 1982's 1999 (the band does appear on the in-concert rave-up, "It's Gonna Be a Beautiful Night"), and he sounds liberated, diving into territory merely suggested on Around the World in a Day and Parade. While the music overflows with generous spirit, these are among the most cryptic, insular songs he's ever written. Many songs are left over from the aborted triple album Crystal Ball and the abandoned Camille project, a Prince alter ego personified by scarily sped-up tapes on "If I Was Your Girlfriend," the most disarming and bleak psycho-sexual song Prince ever wrote, as well as the equally chilling "Strange Relationship." These fraying relationships echo in the social chaos Prince writes about throughout the album. Apocalyptic imagery of drugs, bombs, empty sex, abandoned babies and mothers, and AIDS pop up again and again, yet he balances the despair with hope, whether it's God, love, or just having a good time. In its own roundabout way, Sign 'O' the Times is the sound of the late '80s -- it's the sound of the good times collapsing and how all that doubt and fear can be ignored if you just dance those problems away.