His second movie, "Under the Cherry Moon," had just bombed at the box office. His engagement to singer Susannah Melvoin had ended. And Prince had dismissed his longtime backup band, the Revolution.
"You're turning 30, your reign has ended, the world is changing, the current styles of music are not what you do. And you've got this new band coming in," said Susan Rogers, his personal recording engineer from 1983 to 1987. "There was doubt in the room. Prince is not used to doubt. He didn't have the experience or the tool kit for understanding."
So Prince did what he always did - expressed his feelings in song. Lots and lots of songs.
In March 1987, exactly one year after trotting out the "Parade" LP, the international superstar delivered "Sign o' the Times." Rogers called it "a transitional album." Critics called the Purple One's ninth studio project his best album to date, superior to the blockbuster "Purple Rain."
The subject of a new super-deluxe reissue featuring 92 tracks, "Sign o' the Times" still holds up as the Minneapolis musician's masterwork 33 years later.
With its 16 original tunes, the wildly adventurous double disc embraced Prince's broadest musical palette, everything from new wave and gospel to funk and pop. Moreover, it proffered a wide range of messages, from entreaties to dance and incisive social commentary to sexy seductions of love and shout-outs to the Lord.
In this new reissue, dozens of previously unreleased tracks from his storied Paisley Park vault further illustrate his unstoppable explosion of creativity in this period.
"Sign o' the Times" was actually an outgrowth of several projects he recorded and shelved in the post-"Purple Rain" heyday - "Dream Factory," "Crystal Ball," "Black Album" and "Camille."
"'Dream Factory' and 'Crystal Ball,' they were made out of leftovers," said Lisa Coleman, who played keyboards with Prince from 1980 to 1986. "He didn't really talk about the concepts. The songs would come first and then he'd decide where they should go."
In fact, 11 tracks on the original "Sign o' the Times" were written and first recorded with the Revolution.