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Ten Perplexing Mysteries in Pop Music

by MIchael Atkins-Prescott
fact checked by Darci Heikkinen

Pop culture is for everyone. In a world where we expect 24/7 access to entertainment, pop culture is the air that we breathe. The pop that we consume is frequently an identity marker, and for that reason, people devote inordinate amounts of time to learning everything there is to know about their favorite celebrities, TV shows, movies, and rock bands.

This has been made all the more effortless by the internet, which has created a world where we’re just not used to information that’s unknowable and out of our reach. This makes the truly unsolved mysteries both frustrating and tantalizing. So, let’s look at 10 mysteries that have perplexed music lovers for years. While some have seen movement toward being solved, others still leave us stumped!

Related: 10 (Un)Popular Opinions on the Mysteries of The Sopranos

10 “Like the Wind”–The Most Mysterious Song on the Internet


The most mysterious song on the internet, most commonly dubbed “Like The Wind,” should be an open-and-shut case; if a song was played on a commercial radio station, then surely someone should know it, right?

In or around 1984, a teenager named Darius S. made a mixtape of songs he’d recorded off the radio. He listed all the track names on the insert slip, but for “Like the Wind,” he just put a question mark. In 2004, his sister, Lydia H., put the song on the internet in an attempt to identify it. Two decades later, we are still no closer to an attribution, despite Internet sleuths putting ridiculous amounts of effort into the search.

Forensic analysis has narrowed the original broadcaster down to the German station NDR 1. However, no one at the station has been able to offer any other information. Many other possible leads have turned out to be hoaxes. If one were to write a song designed to launch such a mystery, one could not do much better than “Like the Wind.”

“Like the Wind” sounds eerily like it was beamed in from a parallel dimension. It’s an absolute banger. The lyrics are impossibly garbled by tape distortion (another tantalizing mystery). They are sung in an unearthly baritone reminiscent of Joy Division’s Ian Curtis and are accompanied by highly strung major key new wave guitar work. “Like the Wind” is unforgettable because it sounds like every ’80s new wave song, while also sounding like nothing else.[1]

9 Who Is Carly Simon’s “You’re So Vain” About?

Carly Simon – You’re So Vain

As possibly pop culture’s greatest mystery, “You’re So Vain” is one of those songs whose lyrics are so clear, concise, and cutting that any question they leave unanswered is beguiling. The song contains so many specific details that it must be about a single identifiable person, right?

At first, Carly Simon claimed the song was not about one man but about men plural, a compound character. But she later claimed it was three men. Since two of these identities have been confirmed—actor Warren Beatty and author Nick Delblanco—we are on the hunt for just one man.

In 2009, Simon gave us our biggest break when she said that the name was hidden in a new rerecording of the song. A day later, reports came out that the name “David” was backmasked on the track. Vanity Fair investigated all the Davids in Simon’s life and produced some compelling theories, but nothing conclusive.[2]

8 What Happened to Richey Edwards of the Manic Street Preachers?

La Tristesse Durera (Scream to a Sigh) (Remastered) [Official HD Video]

In February 1995, when alt-rock icon Richey Edwards disappeared, it was less than a year after the death of Kurt Cobain. As Edwards’s car was found near the Severn Bridge, a notorious suicide spot, the parallel was hard to miss. Both men famously battled depression and mental health issues, and both are members of the infamous “27 Club.”

But unlike Cobain, Edwards never left a suicide note, and no body was ever found. Where Cobain’s death was unambiguously a suicide, Edwards’s disappearance raises more questions. Fans have supposedly spotted Edwards in Goa, India, and the Canary Islands. Edwards’s family has criticized the investigation into his disappearance, and though they had the option of having him declared “presumed dead” in 2002, his status remained “missing” until 2008.[3]

7 Who Murdered Tupac and Biggie?

2Pac vs Biggie: From Friends To Enemies

The murders of Tupac Shakur and the Notorious B.I.G., almost exactly six months apart and suspiciously similar, are pop culture’s most infamous cold cases. But it’s Tupac’s murder that gets the most attention, as the popular narrative that Biggie was killed in retaliation for Tupac’s murder makes the Biggie case seem a little less mysterious. We may not know who pulled the trigger in the Biggie case, so the narrative goes, but the biggest question, “why,” is an open and shut case.

But that narrative was turned on its head in September 2023 when Duane “Keefe D” Davis was indicted by a grand jury for Tupac’s murder, making it plausible that the case may actually be solved. This throws into relief all that we don’t know about Biggie’s murder and the alternate narratives, such as the possibility that notorious Death Row Records founder Suge Knight conspired with a corrupt LAPD officer to make the murder appear to be the result of a hip-hop beef.

Biggie’s mother, Violetta Wallace, has twice sued the city of Los Angeles for the wrongful death of her son based on this theory.[4]

6 Publius Enigma, Pink Floyd’s Unsolvable Puzzle

Pink Floyd – Keep Talking (Publius Enigma)

Have you ever wondered what would happen if there was a promotional puzzle competition that no one solved?

That puzzle would go from being an insignificant commercial promotion to being a mystery for the ages. In 1994, as Pink Floyd was promoting their album The Division Bell, a user going by the name Publius posted a message on the then-very-nascent internet that read…

“My friends. You have heard the message Pink Floyd has delivered, but have you listened? Perhaps I can be your guide, but I will not solve the enigma for you. All of you must open your minds and communicate with each other, as this is the only way the answers can be revealed. I may help you, but only if obstacles arise.”

The legitimacy of the message was confirmed when, at a concert in East Rutherford, New Jersey, lights at the front of the stage spelled out “Enigma Publius.”

A further message added that clues were hidden in the lyrics and artwork of The Division Bell—the requirement that one buy the album raised suspicions that the Publius Enigma was a ploy to sell records. Drummer Nick Mason and guitarist David Gilmour both confirmed these suspicions.

It may be that Publius Enigma remains unsolved because Pink Floyd fans were too cynical to play along with a publicity stunt. If that’s the case, then it’s ironic that a genuine mystery has such a cynical origin, considering the record label or ad men or whoever was behind Publius Enigma probably gave up on providing further clues, making the puzzle literally unsolvable, like a jigsaw with missing pieces.[5]

5 What Happened to Q Lazarus?

Goodbye Horses – Q Lazzarus

The fate of Q Lazarus is the only mystery on this list that’s been conclusively solved, but I don’t think any solution will ever feel satisfactory. In a world where one can find out any celebrity’s BMI with a Google search, the thorough disappearance of an up-and-coming star from the public eye seems impossible. Yet, after her songs were featured in a string of critically acclaimed box office hit movies, Q Lazarus disappeared from the public eye for nearly twenty years while internet speculation about her whereabouts grew to a fever pitch.

In the ’80s, Q—real name Diane Luckey—was working as a taxi driver when she picked up film director Jonathan Demme while a demo tape of her music played on the stereo. As a result of that chance encounter, her song scored the most iconic scene in Demme’s most iconic film The Silence of the Lambs. The song “Goodbye Horses” became a cult hit. She was also featured in Demme’s next Oscar-winning film, Philadelphia.

In 2015, the New York Post reported that a licensed bus driver named Diana [sic] Luckey was the lead plaintiff in a class action lawsuit against a Staten Island bus company for refusing to hire female drivers. Four years later, documentary filmmaker Eva Aridjis confirmed this was Q when the two became friends after a chance meeting while Q was working for a car service.

Q Lazarus passed away in 2022, and Aridjis is working on a documentary about her late friend to be released this year. But regardless of how many questions the documentary answers, the story of the rock star who wasn’t, who was discovered and then rediscovered thirty years apart in almost identical ways, will always be mysterious.[6]

4 The Curse of the Grateful Dead

Friend of the Devil (Live at Radio City Music Hall, New York, NY 10/27/80) (2018 Remaster)

In 2014, Todd Matthews, national director of the National Missing & Unidentified Persons System (NamUs), made a strange observation. One “commonality,” as he called it, linked a startling number of the cold cases in the database—they were all associated with psychedelic folk survivors The Grateful Dead. He compiled a list of twelve missing, unidentified, or murdered Grateful Dead fans on a website devoted to solving their cases.

The earliest of the cases on Matthews’s website is the case of Bonita Mara Bickwit and Mitchel Fred Weiser, who disappeared while hitchhiking to a Grateful Dead concert in 1973. The latest is an unidentified woman whose body was discovered by a fisherman in Isleton, California, in 2008, wearing a Grateful Dead jacket.

In between, there was the case of Bridget Lee Pendell-Williamson, who disappeared in 1996 while following the Dead; Douglas Simmons, who went missing at a Grateful Dead concert in 1993; an unidentified man who died in a car accident in 1995 with Grateful Dead concert ticket stubs in his pocket; and an unidentified woman discovered in New Jersey in 1991 with Jerry Garcia’s iconic crouching tiger emblem tattooed on her thigh.

In 2020, podcasters Jake Brennan and Payne Lindsay discovered another apparent case of the Grateful Dead curse. Mary Gioia and Greg Kniffin were murdered at a Deadhead fan encampment in 1985. A 31-year-old Black man was sentenced to death for their murder and died in prison shortly after his conviction was overturned.[7]

3 The Death of the Rollimg Stones’ Brian Jones

The Rolling Stones – No Expectations (Official Video) [4K]

Brian Jones was not just one of the founding members of The Rolling Stones; he was the founding member, recruiting the others and giving the band its name. However, as the band’s sound developed away from Jones’s vision, he developed drug issues and became increasingly unreliable. In 1969, he was dismissed from the band and passed away less than a month later from drowning.

However, there is a theory that Jones was murdered by a construction worker working on his home in a payment dispute. The Stones’ infamous fixer Tom Keylock claims that the construction worker, Frank Thorogood, confessed on his deathbed. The murder scenario was profiled on the British crime reenactment show Crimewatch in 1994 and in the book Who Killed Christopher Robin? by journalist Terry Rawlings. Jones’s daughter, Barbara Marion, also believes he was murdered.

Frustratingly, if Keylock is to be believed, then Jones’s murder was covered up by the police to conceal mistakes they’d made in their investigation.[8]

2 Was David Bowie’s Blackstar a “Farewell” Album?

David Bowie – Lazarus (Video)

In 2016, David Bowie passed away from liver cancer two days after releasing his final album, Blackstar, an album full of arcane references to death. It seemed as if there was only one way to interpret the album—as a farewell to his fans and a confession of the illness he’d kept secret from the public. It seemed inconceivable that Bowie did not intend Blackstar to be about his own death. The video for Blackstar’s second single, “Lazarus,” shows Bowie on his deathbed ascending to heaven as he sings the chilling opening line, “Look up here, I’m in heaven.” How could this not be a message, one might ask?

However, according to Johan Renck, who directed the “Lazarus” video, Bowie did not learn that his treatment would be stopped until partway through shooting the video and that he, not Bowie, came up with the video’s concept. While Ivo Van Hove, with whom Bowie collaborated on an off-broadway production in his final months, even after treatment was stopped, Bowie was not resigned to death and was determined to continue making music.

If Bowie had survived, there’d be no reason to link Blackstar’s morbidness with Bowie’s own mortality. If Bowie expected he’d survive, then the obvious interpretation of Blackstar is not so obvious after all.[9]

1 Who Is the Model on the Cover of Small Change by Tom Waits?

Tom Waits – “Invitation To The Blues”

The cover art for Tom Waits’s unlikely 1976 breakthrough shows Waits looking glamourously disheveled in a go-go dancer’s dressing room while a glamourously bored-looking go-go dancer in pasties and a g-string mopes in the background. The model is said to be Casandra Peterson, better known as Elvira Mistress of the Dark, host of Elvira’s Movie Macabre.

But according to Peterson, there’s at least a possibility it’s not her. In 2009, she told the AV Club, “I don’t remember having done it. But of course, I don’t remember a lot of stuff I did in the ’70s. I went straight from the ’60s to the ’80s; I don’t know what happened to that decade. But it looks like me! I’ve stared at it really, really hard, and I’m pretty sure it’s me…. But I don’t remember that one.” She later added, “I just look and look and look at it and go, ‘It doesn’t look exactly like me.’” and “I would just think that I would remember modeling for the cover of an album with Tom Waits, who I’ve always loved.”

When asked if she’d ever reached out to Tom Waits to seek clarification, she expressed doubt that he’d remember that period either.[10]

fact checked by Darci Heikkinen