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The 50 Worst Decisions in Music History

Horrible business moves, artistic blunders, deeply questionable moral judgment — with appearances by Adam Levine, Kiss, Kanye West, and many more

Kanye West, Justin Timberlake, Janet Jackson, Ashlee Simpson, Adam Levine, Taylor Swift IMAGES IN COMPOSITE BY CHRIS HASTON/NBCU PHOTO BANK/GETTY IMAGES; KMAZUR/WIREIMAGE; DANA EDELSON/NBCU PHOTO BANK; JEFF KRAVITZ/FILMMAGIC; ZHENGSHUN TANG/GETTY IMAGES

IN THE WORDS of the 18th-century poet Alexander Pope, to err is human. But most of us regular humans make mistakes on pretty small scales, like leaving our house keys at work or forgetting to order fries in the drive-through. When rock stars screw up, they do it in epic, spectacular ways, with consequences that are often catastrophic.

They can lead to decades of bitter questions: “What if I didn’t wear that pink tank top in the music video? What if I didn’t say we were bigger than Jesus? What if I hadn’t given the Nazi salute at that British train station?”

But there’s no take-backs in life. Rock stars, like the rest of us, have to live with the consequences of their actions forever. In this list, we look back at the long history of rock stars’ fuckups and call out the 50 biggest ones. To be clear, we limited this largely to professional decisions that impacted careers. Many rock stars have done horribly destructive things when it comes to drugs or their treatment of women, but that’s a whole other list.

From Rolling Stone US

11

Steve Van Zandt quits the E Street band just before ‘Born in the USA’ tour

Steven Van Zandt’s friendship with Bruce Springsteen goes all the way back to their teenage years in the mid-Sixties, and they played together in numerous bands in the early Seventies. Van Zandt joined the E Street Band shortly after Born to Run was recorded in 1975, and the years that followed were marked by a lot of tours and not a lot of money. The real cash wouldn’t come until Born in the USA finally gave the band the sort of pop success that could elevate them to stadiums, but Van Zandt quit before it came out to devote himself fully to his solo career. “It’s the one defining moment of my life,” Van Zandt told Rolling Stone in 2020. “It was a mistake I’ve never recovered from. Financially, it was apocalyptic. That said, we did take years off the life of the South African government [Van Zandt created Artists United Against Apartheid in 1985]. But is that worth losing all of my friends, all of my power base, all my juice, all my celebrity capital to save a few lives? And you’ve got to say, ‘Yeah, sure. It was.’ But I look back and think, ‘Jeez, if only I could’ve done those things and stayed.’ I would’ve had the perfect life.”

10

Billy Squier obliterates his career with one cheesy music video

The early days of MTV were a dangerous time. Acts were shooting videos on shoestring budgets over the course of a few hours, not realizing they were creating indelible images that would define them forever. A great video like Duran Duran’s “Rio” could elevate a group and make them eternally cool, but then there’s the case of Billy Squier’s “Rock Me Tonite.” Directed by choreographer Kenny Ortega, the video shows Squier prancing around a pastel bedroom in a pink tank top. “When I saw the video, my jaw dropped,” Squier said. “It was diabolical. I looked at it and went, “What the fuck is this?” The whole thing is painfully awkward, and it turned off young fans all around the country. It virtually ruined his career and was a very sore subject for several years, but he’s finally come to terms with it. “The wounds have healed and the scars aren’t that deep, because my life has evolved in a good way. I left the music business when I was forty-three. I don’t have to work. Look who’s smiling now! That video is a bad part of a good life.”

9

U2 give their new album away for free in iTunes

U2 moved from clubs to arenas to stadiums over the course of just a few years by thinking big. It was a mentality that served them quite well throughout the Eighties, Nineties, and early 2000s, but they took it a bit too far in 2014 when they linked a deal with Apple in which their album Songs of Innocence would show up for free to every single Apple user’s personal devices. We’re talking about a non-insignificant percent of planet Earth here, and it was quickly revealed that not everyone who owned a phone was by definition a U2 fan. The backlash was swift and brutal, especially since Songs of Innocence wasn’t exactly another Joshua Tree or Achtung Baby in terms of quality. Before long, Apple was forced to create a tool that allowed users to delete the record with a single click. They even set up a support website to guide users through the process. “I’d thought if we could just put our music within reach of people, they might choose to reach out toward it,” Bono said later. “Not quite.”

8

Ja Rule invests in the Fyre Festival

There are all sorts of places Ja Rule could have invested his money back in 2017. He could have gone with real estate, the stock market, or even Bitcoin and probably made a lot of dough. He decided instead to invest in Billy McFarland’s Fyre Festival. Working together, they booked Pusha T, Tyga, Desiigner, Blink-182, Major Lazer, Disclosure, and many others for an exotic festival on the Bahamian island of Great Exuma. The only problem was they didn’t have nearly enough time or necessary resources to pull off the event. They also had no clue what they were doing at all. In the end, the festival became an Escape From New York-style hellscape for the fans that made it to the island, which didn’t even have adequate food or shelter. Rich hipsters found themselves living in tents instead of luxury cabanas and subsisting on cheese sandwiches while they desperately waited to get the hell out of there. “I truly apologize as this is NOT MY FAULT,” Ja tweeted as the fiasco unfolded. He and McFarland were pummeled with lawsuits, including a $100 million class-action suit. In his defense, when all was said and done, Ja was cleared of any wrongdoing.

7

Blood, Sweat & Tears do a tour sponsored by the U.S. government at the height of the Vietnam War

At the dawn of the Seventies, Blood, Sweat & Tears were one of the most successful groups in America. Hits like “You’ve Made Me So Very Happy” and “Spinning Wheel” were inescapable; they played Woodstock; and they won a Grammy for Album of the Year over the Beatles’ Abbey Road. At the peak of their success, they made the inexplicable decision to go on a State Department-sponsored tour of Poland, Romania, and Yugoslavia. The idea was to bring American culture to the Soviet-controlled Eastern Bloc. But mistrust of the U.S. government was at an all-time high due to the Vietnam War, and Blood, Sweat & Tears couldn’t help looking like government propaganda pawns — which is, more or less, what they were. The band was never able to recover its reputation. Five decades later, they even agreed to participate in a documentary called What the Hell Happened to Blood, Sweat & Tears? that goes deep into the saga.

6

Kayne West kicks off his “total asshole” era by interrupting Taylor Swift at the VMAs

When future music historians try to pinpoint the exact moment that Kanye West started moving from hero to villain, they’re likely to pinpoint the 2009 MTV Video Music Awards. That’s the night he stormed the stage while Taylor Swift was delivering her Best Female Video acceptance speech for “You Belong to Me.” “Yo, Taylor, I’m really happy for you,” he said. “I’ma let you finish, but Beyoncé had one of the best videos of all time! One of the best videos of all time!” West was thrown out of the show, and even President Obama called him a “jackass” for the stunt. This seems like a minor incident considering all the madness that would follow, but the long, dark, winding road to the Trump hat and “def con 3 on Jewish people” and showing  porn to his employees and everything else begins here.

5

Woodstock Organizers celebrate event’s 30th anniversary with a horrific riot

In theory, a 30th-anniversary celebration of Woodstock in 1999 made a lot of sense. The 25th commemoration in 1994 was a huge success, and there simply weren’t many festivals in America at that point. Why not gather up some of the biggest bands on the planet and hold a three-day party? It turns out that there’s a lot more to a successful festival than booking bands and selling tickets. You need adequate toilet facilities. You need a way to get water to everyone that doesn’t involve selling them $4 bottles. You need trained security guards. You need places where people can find shelter or even just shade if it’s extremely hot. You need to find a better location than an old, grim disused Air Force base in upstate New York. Woodstock 1999 didn’t have any of those things. It’s not surprising it ended with riots, bonfires, and horrific stories of sexual abuse. The organizers tried to put together a 50th-anniversary event in 2019, but it imploded after they announced a lineup with great fanfare at a New York City press conference.

4

Eric Clapton goes all-in on vaccine conspiracy nonsense

Up until 2020, Eric Clapton had a pretty sterling reputation in the rock community. Detractors pointed to his shockingly racist onstage tirade in 1976, but that was largely swept under the rug or dismissed as the product of way too much cocaine. But then the pandemic hit, and Clapton joined the chorus of loons spouting ridiculous lies and conspiracy theories about Covid vaccines. He even recorded songs about the matter. “This has gotta stop,” he sings on “This Has Gotta Stop.” “Enough is enough/I can’t take this BS any longer/It’s gone far enough/If you wanna claim my soul/You’ll have to come and break down this door.” It’s the single worst song in Clapton’s vast catalog, and many fans will never look at him the same way again.

3

Decca Records passes on signing the Beatles

The decision by Decca records to turn down the Beatles after an audition in January 1962 has been written about so many times that it’s hard to separate myth from fact. Beatles manager Brian Epstein said he was told by Decca head Dick Rowe that “guitar groups are on their way out,” but Rowe insisted this was a complete fabrication. What’s known for sure is that the Beatles put down 15 songs on tape for Decca on Jan. 1, 1962 — and that Decca rejected the fledgling group. The label signed Brian Poole and the Tremeloes instead. This was obviously an enormous blunder that cost Decca countless millions, but let’s be happy it happened, since it put the Beatles on a course that led them to George Martin and all the music they made together.

2

Jerry Lee Lewis marries his underage cousin

When Jerry Lee Lewis traveled to England for his first overseas tour in 1958, he decided to bring his new wife. When he landed at Heathrow airport, a reporter asked the young woman to identify herself. “I’m Myra,” she said. “Jerry’s wife.” The reporter then turned to Jerry and asked how old she was. “Fifteen,” he said. The press dug into the story and quickly found out that she was actually 13, and she was his cousin. The shock sparked headlines all across the globe. The tour was largely canceled, and Lewis found himself unable to book more shows or land more hits on the charts. He eventually restarted his career as a country artist, and he made good money on the Fifties nostalgia circuit, but the scandal followed him for the rest of his life no matter how many times he tried to explain it away. “I plumb married the girl,” he told one reporter. “Didn’t I?”

1

The Rollings Stones hire the Hells Angels as security guards for their rock festival

The Rolling Stones made a lot of mistakes when they decided to end their 1969 American tour with a huge, Woodstock-esque free concert in California. They messed up by initially trying to book it at Golden Gate Park without having enough time or manpower to make that happen, forcing them to move it at the last minute to Altamont Speedway. They messed up by not bringing in enough toilets or food to accommodate the crowd, and by building a stage just 39 inches off the ground. The last mistake required them to hire a security detail to surround the stage, and this led to the biggest mistake of all: Bringing on the Hells Angels to provide that security. The decision has been blamed on the Grateful Dead or Jefferson Airplane, but the Stones signed off on it. This led to the death of fan Meredith Hunter at the hands of the Angels, and roughly 50,000 essays about how the incident marked the end of the Sixties dream.