Every few years, when an up-and-coming musician releases an album after their high-profile breakup is splashed across the front pages of tabloids, people are surprised to re-learn that the inspiration for songs sometimes comes directly from the lives of people who wrote them. This has happened virtually since the beginning of songwriting itself, but contemporary music has become a constantly expanding repository of classics whose origins sprung up from their most painful and profound experiences, the relationships that dominated portions of the artists’ lives, or just chance encounters that lodged in their memories and touched their souls. In some cases, these artists intended to memorialize these important individuals, calling them out by name. But more often, their identities faded into obscurity while the songs about them became a part of the cultural firmament.
Mental Floss already made a list about one of music’s most famous muses, Pattie Boyd, whose relationships with George Harrison, Eric Clapton, and then-future Rolling Stones member Ronnie Wood led to no fewer than 10 different songs. But scanning the recent (and not-so-recent) history of popular music, there are many men and women whose exploits, and their impact, became the basis for some stone-cold classics across many different genres. We’ve collected just a few of the biggest hits to reveal the real-life people now immortalized in art.
1. Johnny Cash // “I Walk The Line” (1956)
In the Johnny Cash biopic of the same name, the iconic country-western singer created the track as a defining moment in his musical career, which later became an interlude to woo June Carter. But a more detailed history of the song reveals that it was actually written specifically for and about his first wife, Vivian, in a powerful declaration of fidelity since he’d just married her a few years prior.
2. Astrud Gilberto with Joao Gilberto and Stan Getz // “The Girl From Ipanema” (1964)
Few songs have set off a wave of interest in a previously unknown genre more fervently than this song did for bossa nova, the Brazilian form of jazz that become a worldwide phenomenon. The composers wrote it about 17-year-old Heloisa Eneida Menezes Paes Pinto, the woman described so attractively in the song, who would pass by—and occasionally pop in to buy cigarettes for her mother—at the Veloso cafe where they would work. She later became a model and a swimsuit store owner in São Paolo, but she was best immortalized with this timeless standard.
3. The Beatles // “Something” (1969)
The aforementioned Pattie Boyd was, by all accounts, a powerful inspiration for rock artists of the 1960s and 1970s, beginning with George Harrison, her first husband. Boyd confirmed her influence on the song in an autobiography, recalling a conversation where he admitted as much, but Harrison later denied it, suggesting it reflected his encroaching interest in Indian culture and the Hindu deity Krishna. Nevertheless, it became one of The Beatles’s most beautiful and famous songs.
4. Johnny Cash // “A Boy Named Sue” (1969)
With a title this conspicuous, Johnny Cash’s famous tune had to have been about somebody real, right? Well, it was, but first of all: he didn’t write the song himself. Where The Sidewalk Ends author Shel Silverstein did—about his friend and fellow writer Jean Shepherd (the narrator of A Christmas Story, which is based on his stories), who endured endless teasing as a child because of his feminine-sounding name.
5. The Rolling Stones // “Wild Horses” (1971)
Originally written as a lullaby for Keith Richards’s two-month-old son, Mick Jagger took the song and rewrote it to focus on his then-relationship with fellow performer Marianne Faithfull. This led to two versions of the song, one by Gram Parsons, but it became a staple of their discography and one of the most delicate love songs ever recorded.
6. Carly Simon // “You’re So Vain” (1972)
Although Carly Simon has declined to publicly name all of the individuals who inspired this song that famously calls out a subset of the Hollywood glitterati for their narcissism, she admits that the second verse is actually about Warren Beatty, a famously attractive (and perhaps justifiably self-obsessed) movie star who was one of her former lovers.
7. Roberta Flack // “Killing Me Softly” (1973)
Before Lauryn Hill covered the song as a member of The Fugees, and even before Roberta Flack made it her signature song, “Killing Me Softly” was first co-written and performed by Lori Lieberman in 1971, about songwriter and performer Don McLean. McLean, famous for “American Pie”—his tribute to early rock ‘n’ roll legends Buddy Holly, The Big Bopper, and Richie Valens, who died in a 1959 plane crash—performed at a club where Lieberman was attending. She was so stricken by his music that she began jotting down lyrics, which were fleshed out by veteran songwriter Norman Gimbel and given music by Charles Fox. Fox and Gimbel later attempted to take credit for the song, minimizing Lieberman’s contributions, but there were too many accounts from all three in print by that point, ensuring that the young singer would remain attached to the mesmerizing tune for good.
8. Dolly Parton // “I Will Always Love You” (1974)
Many people associate this song singularly with Whitney Houston after she recorded one of the barn-burner covers of all time for The Bodyguard soundtrack, but Dolly Parton was actually the author of this song a decade and a half earlier. Parton has since revealed that she wrote this and her signature song “Jolene” in the same night, but this single, which quietly and elegantly says goodbye to a former partner, was inspired by her mentor Porter Wagoner after the two ended a seven-year collaboration.
9. Fleetwood Mac // “Go Your Own Way” (1976)
Few subgenres feature more direct inspiration for their content and lyrics than breakup songs, and few acts have mined that territory for more musical gold than Fleetwood Mac. Not one but two songs on their 1977 album Rumours came from the romantic turmoil of its members, particularly Lindsey Buckingham and Stevie Nicks. Though their relationship had soured by the recording of their eleventh album, the duo managed to get through the recording process in the best way they could: by recording all of its parts separately and overdubbing them in the studio.
10. Phil Collins // “In The Air Tonight” (1981)
Many stories have been associated with Phil Collins’s leadoff single from his solo career after working as the drummer for Genesis, including the supposition that it’s about a suicidal friend he rescued. But if the inspiration is slightly less specific, Collins has indicated its bleak tone was inspired by his divorce from his first wife, Andrea Bertorelli, which additionally prompted him to go on hiatus from Genesis and led to his hugely successful solo career.
11. Journey // “Don’t Stop Believin'” (1981)
Karaoke singers and drunk barflies know this iconic Journey song by chapter and verse, but its conception was inspired by failure. Not long after keyboardist Jonathan Cain moved to Los Angeles to pursue his musical dreams, he would call his father for advice and a pep talk. His father would repeatedly tell him, “don’t stop believing, or you’re done.” He eventually turned those words of wisdom into the hook for one of the most famous songs ever recorded about perseverance.
12. Billy Joel // “Uptown Girl” (1983)
This doo-wop song from piano man Billy Joel is one of the few examples from our list that’s kinda-sorta about two different people, not just one. Although Joel originally wrote it about supermodel Elle Macpherson, who was his girlfriend at the time, it eventually became about Christie Brinkley, whom he later married.
13. Peter Gabriel // “In Your Eyes” (1986)
Rosanna Arquette was a muse for more than one musical artist, with at least one song directly named after her—Toto’s “Rosanna.” But she was living with Peter Gabriel at the time this song was released, and it was later her influence that convinced the singer to license it to Cameron Crowe for the movie Say Anything…, which re-popularized it three years later.
14. Alanis Morissette // “You Oughta Know” (1995)
With the release of her third studio album Jagged Little Pill, Alanis Morissette made a stark transition from the bubblegum pop that established her in Canada to gritty, honest alt-rock, starting with this first single. Like her musical successor Taylor Swift, Morissette isn’t one to kiss and tell—she has never publicly confirmed who the song is about—but comedian and Full House star Dave Coulier has said in interviews that not only do details in the lyrics correspond to circumstances in their relationship, but that she later told him it was about him. (Though he has also denied that the song is about him, so …)
15. No Doubt // “Don’t Speak” (1996)
No Doubt frontwoman Gwen Stefani has not only inspired some great songs, but written them herself, and this Grammy-nominated mid-tempo ballad may be among the best. Although she and her brother Eric originally wrote it as a love song, Stefani modified the lyrics to reflect her relationship with No Doubt bandmate Tony Kanal after their seven-year relationship came to an end.
16. Amy Winehouse // “Me & Mr. Jones” (2006)
Amy Winehouse frequently spun hay into gold with her personal relationships, most frequently with her one-time husband Blake Fielder-Civil. But she also drew generously from the music and good experiences in her life, as on this tune that came out of a Nas concert she attended in Brixton in 2005. Nas has since confirmed that the song is about him, but the clues are there in the lyrics, even if she never mentions the rapper by name—instead referencing his daughter and the bit of trivia that they all share the same birthday.
17. Pink // “So What” (2008)
No one would mistake this track from Pink’s album Funhouse for a romantic tribute, with lyrics like “I guess I just lost my husband / I don’t know where he went.” But during a particularly strained moment in their relationship, the performer carved out this song about her husband, motocross racer Carey Hart. They were estranged at the time, but he appeared in the music video for the song. After they later reconciled, Pink—who described the tune as a “vomiting of truths” about their relationship—invited him to appear in the song’s music video, which he reportedly didn’t realize was about him until he showed up and started listening to the lyrics.
18. Taylor Swift // “Dear John” (2010)
Taylor Swift is frequently targeted by critics for turning her tumultuous love life into fodder for the pop charts—as if hundreds of artists before her haven’t done the same. But this track from her 2010 album Speak Now was written about and inspired by John Mayer, who she dated a year prior. Swift never officially confirmed that the song was about him, but Mayer did it for her, as the narrator sings about a troubled relationship with an older man. In 2012, Mayer told Rolling Stone that he was “really humiliated” by the song. “It made me feel terrible, because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”
19. John Legend // “All Of Me” (2013)
John Legend has always been a balladeer, but this Grammy-winning, piano-driven song ranks among his most memorable, about his then-fiancée (and soon-to-be-wife) Chrissy Teigen. Legend has undoubtedly written more about his wife in the years since, but Teigen told HuffPost which lyric confirmed that this was a big one: “The first line of it is ‘What would I do without your smart mouth,’ so if that’s not about me I don’t know what is,” she said.
20. Ariana Grande // “Thank U, Next” (2018)
In her short career, Ariana Grande has been associated with several famous exes, and she mentions them all on this song of empowerment and liberation. Delightfully, Grande succinctly characterizes her time with each—rappers Big Sean and the late Mac Miller, soccer player Ricky Alvarez, and comedian Pete Davidson—while encouraging her fans to seek grace in dealing with their romantic pasts, even if the goal is simply to let go and move on to the next one.
21. Blake Shelton // “Turnin’ Me On” (2018)
Decades after she penned the iconic breakup song “Don’t Speak,” Gwen Stefani became the subject of a tribute by her then-boyfriend (now-fiancée) Blake Shelton. Shelton doesn’t mention Stefani’s name, but in true media conglomerate fashion, he name-drops the company with which she has a cosmetics endorsement deal, singing, “She’s Revlon red in the blackest night.”
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The Biggest Song From Every Year in the 1960s
From “Surfin U.S.A.” to “Hey Jude.”
ByEden Gordon|Oct 16, 2026, 10:00 AM EDT
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The 1960s saw the rise of the Beatles, the ascension of the Beach Boys and their California dreams, and many cultural sea changes. The biggest songs from each year of this decade include some iconic tracks that remain beloved today, but others might surprise you. From pro-war hits to songs by fictional rock bands, the biggest songs in the U.S. in the 1960s according to Billboard magazine’s year-end Hot 100 rankings are as varied as the decade itself.
- 1960 – “Theme from A Summer Place” // Percy Faith and His Orchestra
- 1961 – “Tossin’ and Turnin’” // Bobby Lewis
- 1962 – “Stranger on the Shore” // Acker Bilk
- 1963 – “Surfin U.S.A.” // The Beach Boys
- 1964 – “I Want to Hold Your Hand” // The Beatles
- 1965 – “Wooly Bully” // Sam the Sham and the Pharaohs
- 1966 – “The Ballad of the Green Berets” by SSgt. Barry Sadler
- 1967 – “To Sir With Love” // Lulu
- 1968 – “Hey Jude” // The Beatles
- 1969 – “Sugar, Sugar” // The Archies
1960 – “Theme from A Summer Place” // Percy Faith and His Orchestra
The biggest song of 1960 was “Theme from A Summer Place,” a track from the 1959 film A Summer Place starring Sandra Dee and Troy Donahue. Interestingly, the song is not actually the film’s theme; instead, it soundtracks numerous romantic scenes between the two protagonists. A staple of the “easy listening” genre with music by Max Steiner, the tune spent nine weeks atop the Billboard Hot 100 charts during the first year of the 1960s.
1961 – “Tossin’ and Turnin’” // Bobby Lewis
Indianapolis-born R&B singer Bobby Lewis recorded the original version of this 1961 megahit, which spent seven weeks at the top of the Billboard Hot 100 in 1961. The song sold three million copies and was later covered by the likes of the Supremes and the Marvelettes. It was also memorably featured in several films. “When it came out in Animal House, I took my tape recorder to the theater. I wished I had a video camera. I taped it off the screen. What a beautiful scene—John Belushi in a garage all by himself, just sittin’ and listenin’ to ‘Tossin’ and Turnin,’” the late Lewis recalled in a 2011 interview with NJ.com. “They never stopped playing it. They haven’t stopped yet. They’re still playing it.”
1962 – “Stranger on the Shore” // Acker Bilk
Two years before the Beatles had their first No. 1 hit in America, a UK-based clarinetist named Acker Bilk took that very same prize. Bilk, who spent most of his time working in the UK’s live jazz scene, came up with the melody of “Stranger on the Shore” while in a taxi and originally named the tune “Jenny” after his daughter.
When asked to compose the theme song for a BBC TV children’s show, Bilk offered “Jenny.” It was accepted, but the program asked him to change the song’s title to match the show’s name: Stranger on the Shore. The tune became a massive hit in both Britain and in America and spent a week as No. 1 on the U.S. Billboard Hot 100, and was covered by the likes of Santo & Johnny, Duke Ellington, and Herb Alpert. “Stranger on the Shore” has also been extensively sampled and remixed over the years, and certainly has kept cash flowing into Bilk’s pockets. But when asked about it in 2012, Bilk appeared to have tired of the song, telling the BBC, “It’s all right, but you do get fed up with it after 50 years.”
1963 – “Surfin U.S.A.” // The Beach Boys
Brian Wilson drew inspiration for this immortal, sun- and sand-soaked hit directly from rock-and-roll legend Chuck Berry. “I started humming the melody to [the 1958 Chuck Berry single] ‘Sweet Little Sixteen,’ and I got fascinated with the fact of doing it,” Wilson said in Keith Badman’s 2004 book, The Beach Boys. “I thought to myself, ‘God! What about trying to put surf lyrics to ‘Sweet Little Sixteen’s’ melody?’” Berry may have been in prison at the time and Wilson didn’t actually surf himself, but what emerged from their one-sided collaboration was “Surfin’ U.S.A.,” a song that cemented a vision of California as a sunny paradise in the minds of millions of listeners. The track became the Beach Boys’ first top-five hit, and while it never reached No. 1 on the Billboard Hot 100, it spent a total of 25 weeks on the chart in 1963.
1964 – “I Want to Hold Your Hand” // The Beatles
At 21, Paul McCartney was living with his girlfriend, Jane Asher, and her family. It was there that he and John Lennon crafted their first track to reach No. 1 in America. “In ‘I Want to Hold Your Hand,’ I remember when we got the chord that made the song,” Lennon said in 1980. “We were in Jane Asher’s house, downstairs in the cellar playing on the piano at the same time. And we had, ‘Oh you-u-u…got that something…’ And Paul hits this chord and I turn to him and say, ‘That’s it!’ I said, ‘Do that again!’ In those days, we really used to absolutely write like that—both playing into each other’s nose.”
Asher was the first to hear the track, which became the band’s third British No. 1. “We were booked to go to America directly after the Paris trip, so it was handy to have a No. 1,” George Harrison recalled. “We’d already been hired by Ed Sullivan, so if it had been a No. 2 or No. 10, we’d have gone anyway, but it was nice to have a No. 1.” It stayed at the top of the Billboard Hot 100 for seven weeks before being replaced by another Beatles hit: “She Loves You.”
1965 – “Wooly Bully” // Sam the Sham and the Pharaohs
“Wooly Bully” was musically inspired by the 1952 track “Hully Gully Now” by Big Bo and Little Smitty, but Domingo Samudio—also known as Sam the Sham—put his own Tex-Mex spin on it. Recorded in Memphis’s Sun Studios, the track became a smash.
Urban legend holds that the song was named after Samudio’s cat, but the famously hearse-driving, turban-wearing musician has denied this. “People make up all kinds of stories when they don’t have the right answers,” Samudio said, according to the Memphis Music Hall of Fame. Regardless, the song became the first American tune to sell a million copies during the British Invasion, and while it never hit No. 1 on the Billboard Hot 100, it spent 18 weeks on the chart that year, the longest of any song in 1965. Per Samudio, “We kicked The Beatles’ butt!”
1966 – “The Ballad of the Green Berets” by SSgt. Barry Sadler
The ‘60s and the ‘70s might be best remembered for the legendary anti-war music that emerged during this time, but the biggest song of 1966 was actually a rare pro-war hit. “The Ballad of the Green Berets” was written and performed by Barry Sadler, who was an active-duty Green Beret medic when he debuted it on the Ed Sullivan Show. The song was deeply controversial at the time due to rising anti-Vietnam War sentiment, but also managed to spend five weeks atop the Billboard Hot 100.
Sadler would go on to have one other hit song before leaving music to write fiction. The remainder of his life was marred by violence; he shot and killed the country singer Lee Emerson Bellamy in 1978 and spent 30 days in prison for that, then moved to Guatemala, was shot in the head, came back to America, and spent the rest of his life in a hospital bed until his death in 1989.
1967 – “To Sir With Love” // Lulu
Glasgow-born musician Lulu played a student in Sidney Poitier’s character’s class in the film To Sir, With Love, and was also slated to sing the title track. Dissatisfied with the songs the producers were considering, Lulu suggested that her friend Mark London try writing one. London initially declined, thinking he had no shot, but came up with a composition in five minutes at Lulu’s behest. That became the basis of “To Sir With Love,” the biggest hit of 1967. Lyricist Don Black penned the words the next day. “I was over the moon,” Lulu said. “I just knew it was going to be a great song.” The tune was never released as a single, but it still soared to the top of the charts and stayed there for five weeks.
1968 – “Hey Jude” // The Beatles
In June 1968, Paul McCartney was driving to meet with John Lennon’s wife, Cynthia, and her son, Julian. John and Cynthia were in the middle of a divorce, and McCartney wanted to find a way to comfort the child he had become close to.
“I thought, as a friend of the family, I would motor out to Weybridge and tell them that everything was all right: to try and cheer them up, basically, and see how they were. I had about an hour’s drive,” he said in the documentary Anthology. “I would always turn the radio off and try and make up songs, just in case…I started singing: ‘Hey Jules—don’t make it bad, take a sad song, and make it better…’ It was optimistic, a hopeful message for Julian: ‘Come on, man, your parents got divorced. I know you’re not happy, but you’ll be OK.’”
What emerged was the resounding, expansive classic “Hey Jude.” “I eventually changed ‘Jules’ to ‘Jude,’” McCartney added. “One of the characters in Oklahoma! is called Jud, and I like the name.”
When McCartney played the song for Lennon and Yoko Ono, he shared that he was thinking of changing the line, “The movement you need is on your shoulder,” but Lennon forbade him from doing so. “John said, ‘You won’t, you know. That’s the best line in it!’ That’s collaboration. When someone’s that firm about a line that you’re going to junk, and he said, ‘No, keep it in,’” McCartney continued. “So of course you love that line twice as much because it’s a little stray, it’s a little mutt that you were about to put down and it was reprieved and so it’s more beautiful than ever. I love those words now…”
Lennon, for his part, felt that the song had been written for him. “The words ‘go out and get her’—subconsciously he was saying, Go ahead, leave me. On a conscious level, he didn’t want me to go ahead,” he said to David Sheff in 1980. “The angel in him was saying, ‘Bless you.’ The devil in him didn’t like it at all because he didn’t want to lose his partner.”
“Hey Jude” has remained widely beloved ever since it was released and frequently tops rankings of best songs of all time. It also spent nine consecutive weeks at the top of the Billboard Hot 100.
1969 – “Sugar, Sugar” // The Archies
Closing out this list of the biggest songs of the ‘60s is a song by a fictional pop band. “Sugar, Sugar” was written by Jeff Barry and Andy Kim. It was performed by The Archies, a band from The Archie Show, a cartoon based on the Archie comics. Ron Dante sang the lead vocals, and Toni Wine provided the female backing vocals. The song was the group’s third single and remains one of the biggest bubblegum pop songs of all time.
“We went into the studio. Jeff and Andy Kim, who had hits on his own as a writer and singer, Jeff and Andy wrote ‘Sugar, Sugar,’ Ronnie was Archie, and I was Betty and Veronica,” Wine later said of the process of creating the song. “We went in, we did the record. It was a fun session, it was a blast, and at the session we just knew that this was something, and something huge was going to happen. We didn’t really know how huge, but it was huge.” It spent four weeks at the top of the Billboard Hot 100 chart.
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