As the Rolling Stones' contentious post-Dirty Work hiatus got underway, Mick Jagger appeared to be moving on. Primitive Cool arrived on Sept. 14, 1987, with many of the same collaborators from his first album. Though there remained a few key reminders of his best days with the Stones, the music his new group made together – both in tone and feel – was quickly modernizing.

The results represented something bigger than a second solo project. Primitive Cool felt like a death knell for one of rock's sturdiest bands.

"I wanted to keep the same core of musicians throughout the album," Jagger told the Chicago Tribune in 1987. "I switched keyboard players, and on some tracks that I wrote with [co-producer] Dave Stewart of Eurythmics, the two of us played rhythm guitars. But I tried to keep the basic group somewhat tighter, to get a consistent feel and establish a bit of an identity. I think I've moved away from the Rolling Stones sound on this record, but I hope I've retained some of the best parts of that sound."

Jagger's career appeared to be building momentum, after he released a pair of Billboard Top 20 songs in 1985 – "Just Another Night," which climbed to No. 12, and the No. 7 "Dancing in the Street" with David Bowie. Little surprise then that he chose to focus elsewhere after the lightly regarded Dirty Work quickly faded. But something happened on the way to the solo coronation.

Primitive Cool was preceded by "Let's Work," a sleek and overtly commercial single that barely cracked the Top 40 in either the U.S. or the U.K. At the same time, the album's subject matter hews more toward home and hearth rather than the typical Stonesy hedonism.

On the title track, Jagger addresses what his children might think of his legacy: "Did you walk cool in the '60s, Daddy?" he sings. "Did you fight in the war? Or did you chase all the whores on the rock and roll rumble?" "Say You Will" displays a strikingly mature approach to relationships, while in "Throwaway" Jagger admits that he "used to play the Casanova" – but now openly pokes fun at a youthful predilection for "cheap champagne, brief affairs and backstage love." "War Baby" closes the album with a stark message about violent conflict.

There were moments when he seemed to be taking direct aim at Keith Richards too. "Did you listen to 'Shoot Off Your Mouth?'" Jagger asked in a 1987 talk with the Los Angeles Times. "Now, who do you think that is about?"

Listen to Mick Jagger Perform 'Throwaway'

As these fissures very publicly widened, a Rolling Stones reunion couldn't have seemed more remote.

Still, Jagger had to admit that he loved this newfound autonomy – whatever its implications. "You don't sort of sit down and say, 'This song is for a Rolling Stones album,' and 'This one is for my own album,'" he told the Times. "You just write songs – though some of them may not fit the Rolling Stones, either musically or lyrically. So, the solo albums give you a bit more freedom. I couldn't imagine the Stones, for instance, doing a song like 'Primitive Cool,' because that song just isn't [what they are about]."

In another clear indication of his solo intentions, Jagger debuted the core group of musicians – including the then-somewhat reclusive Jeff Beck – during a performance-based video for "Throwaway," filmed in hopes of goosing the single along. "This is the first time we've ever appeared in public," Beck told MTV in 1987. "It's quite a moment, really. To watch people's faces, they love [Mick] so much. It takes the strain off me."

Nothing worked, as "Throwaway" never got past No. 67, and neither "Saw You Will" nor the title track managed to chart at all. Perhaps it was a bridge too far for his oldest fans, or maybe the creeping realization that the Rolling Stones' future was in the balance had finally been made clear. Primitive Cool stalled outside the Top 40 in the U.S., a far cry from the platinum sales of Jagger's debut, She's the Boss. A subsequent tour never got past Japan and Australia.

Even his former bandmates were dismissive of Jagger's solo work. “What did he have, two albums? She's the Boss and Primitive Cool?" Keith Richards asked NME in 2015. "They had something to do with ego. He really had nothing to say."

To this point, Jagger seemed resolved to remain out on his own. "My feeling is that I'd very much like to do more Stones projects," he told the Tribune in 1987. "It should happen; I don't see why not. I enjoy doing this, though. It's interesting creating your own vision and creating your own way. With a band, it's a kind of democratic thing, so there's a lot of compromising. The songs go through a lot of changes between the writing and the finished record. When it's your album, you can try something and if it doesn't work, well, it's your fault. I like doing it both ways, really."

The Rolling Stones didn't get back together again until after a debut solo album by Richards was released to wide acclaim in 1988.

Rolling Stones Solo Albums Ranked

They didn't necessarily become huge commercial or critical hits, but some produced career-changing moments anyway.

You Think You Know the Rolling Stones?

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