Keith Richards is usually tenderhearted when it comes to women, despite his outwardly rugged appearance and membership in one of rock's most libidinous bands.

"There wasn't a predatory aspect to [Richards'] involvement with women," Anthony DeCurtis, author of The Rolling Stones: Unzipped, told ABC in 2010. "Beneath his stereotypical portrait – he's willing to embody a pirate-like role that's only part of the picture – there's a sweetness and sensibility towards the women he's been involved with."

Early in his career, Richards' sentimentality helped smooth the way for one of the Rolling Stones' most recognizable hits, "Ruby Tuesday," which appeared as the B-side to "Let's Spend the Night Together" in January 1967.

At the time, Richards was dating Linda Keith, a 20-year-old British Vogue model who he met at a party thrown by the Stones' producer and manager, Andrew Oldham. Keith was best friends with Oldham's then-girlfriend, Sheila Klein. (This same party featured another worthwhile meeting: that of Mick Jagger and singer Marianne Faithfull.)

"The first look was the deepest, watching her with all her tricks and movements, fearfully, from across the room and feeling that hit of longing, and thinking she was out of my league," Richards wrote in his 2010 autobiography, Life. "I was sometimes in awe of the women I was with at the start, because they were the creme de la creme, and I'd come from the gutter as far as I was concerned."

The couple fell for one another, finding common ground in their mutual love of blues music. Richards recalled Linda Keith as being "a blues purist, in fact, who didn't really approve of the Rolling Stones. She never did. She probably doesn't now."

She said Richards was a "blues aficionado, and that was why we got on so well. It completely counteracted his shyness and that's all I wanted to talk about anyway," Keith told the Guardian in 2013, noting that she didn't even allow him to play Rolling Stones records on her turntable. "He knew I was never a huge fan. I was hugely into black music, so they sounded a bit pale by comparison."

While the couple was together, they traveled frequently to America for Stones tours and concerts, where Keith first saw a then-relatively unknown Jimi Hendrix perform in New York City. Keith's initial thought, she recalled, was that Richards "must see this." (Keith even loaned Hendrix one of her boyfriend's guitars, a white Fender Stratocaster, for a showcase performance at Cafe Au Go-Go in New York's Greenwich Village. Hendrix smashed it onstage.)

Listen to the Rolling Stones' 'Ruby Tuesday'

Richards was less interested in getting to know Hendrix and more concerned that his girlfriend was hanging out with such raucous company and, in turn, had developed a dangerous drug habit that Richards himself had yet to pick up. "For me to disapprove then is an irony, but I did disapprove then," Richards later wrote. He called Linda Keith's father, who came to collect his daughter at the Cafe Au Go-Go as soon as he could.

Keith was initially upset at Richards, who met up with her when she returned to the U.K., though she later reconsidered. "There he was, looking rather smug," she told the Guardian. "I told him to fuck off. Keith did do a bit of the dirty on me. But he genuinely felt I was in danger and he could save me. And God bless him, maybe he did."

Linda Keith became, as Richards described it, "the one that first broke my heart." He said it took several years of "growing apart slowly" for the pair to officially call it quits. Richards then turned to music, writing the melancholic tune became "Ruby Tuesday" as a way to bid farewell to Keith: "When you change with every new day, still I'm gonna miss you."

Jagger sang a tender lead vocal, while Brian Jones added the distinctive recorder part. "It’s just a nice melody, really – and a lovely lyric," Jagger told Rolling Stone in 1995. "Neither of which I wrote, but I always enjoy singing it."

Where "Let's Spend the Night Together" begged a lover to stay — "I'll satisfy your every need / And now I know you will satisfy me" — "Ruby Tuesday" offered the gentler juxtaposition: acceptance of a woman's departure: "Don't question why she needs to be so free / She'll tell you it's the only way to be."

"Let's Spend the Night Together" was anticipated to be the bigger hit, but it lost airplay due to controversial lyrics: Ed Sullivan even insisted Jagger edit the lyric from "let's spend the night together" to "let's spend some time together," when they performed the song on his show.

That left room for "Ruby Tuesday" to rise in the charts. It reached No. 3 in the U.K. and became the Rolling Stones' fourth No. 1 hit in the U.S, appearing on the American version only of Between the Buttons. (Singles were often not included on British studio albums.)

For Richards, "Ruby Tuesday" was "one of those things. ... Some chick you've broken up with, and all you've got left is the piano and the guitar and a pair of panties," he said in 2003's According to the Rolling Stones. "It just comes out of that, and after that you just build on it. It's one of those songs that are easiest to write, because you're really right there and you really sort of mean it. And for a songwriter, hey break his heart and he'll come up with a good song."

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