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


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


MC Hammer goes gangsta, “Hammer Time” comes to a screeching halt

MC Hammer was the most commercially successful rapper of the early Nineties, but the scene rapidly shifted once Dr. Dre dropped The Chronic in 1992 and gangsta rap made songs like “U Can’t Touch This” and “2 Legit 2 Quit” feel hopelessly dated. Hammer responded by dropping the MC from his name and trying out his own version of G-funk with his 1994 album, The Funky Headhunter. The video for lead single “Pumps and a Bump” showed Hammer in a disturbingly tight speedo surrounded by women in minuscule bikinis. It was so raunchy that MTV refused to put it in heavy rotation, and the album wound up selling a fraction of his previous records. Would America have accepted Hammer as a gangsta? Probably not. But Hammer as a gangsta in a speedo was definitely a bridge too far.


Mötley Crüe fire Vince Neil and make an industrial album

The dawn of the alternative-rock revolution in the early Nineties was essentially a death sentence for most of the hair-metal bands of the Eighties, but there might’ve been a scenario in which Mötley Crüe somehow survived. They were the biggest band from that scene, Nikki Sixx was (and technically still is) a very gifted songwriter, and their 1989 LP, Dr. Feelgood, was their most popular release to date. If they’d stuck together, worked hard, and built on the momentum of Dr. Feelgood, hanging in there alongside Nirvana wouldn’t have been unthinkable. Instead, they fired frontman Vince Neil, hired journeyman singer John Corabi to replace him, and decided to make an alt-rock album. This process ate up a very long five years, and by the time they reemerged with a self-titled LP in 1994, grunge was already on its way out. They seemed like visitors from another eon, and their tour to support the album played to oceans of empty seats. They reunited with Vince Neil three years later and attempted to plow forward, but by then the number of people who didn’t care had ballooned even more.


Scooter Braun pisses off Taylor Swift

Scooter Braun had no idea who he was messing with in 2019 when he bought Big Machine Label Group, which included Taylor Swift’s master recordings. The music manager behind Justin Bieber, Ariana Grande, and Usher may have thought he could simply scoop off the masters and squeeze them for money, but he didn’t count on Swift going public with her rage over the situation — and rerecording all of her old albums so she’d own the new “Taylor’s Version” masters. He also became public enemy number one to the Swiftie army overnight. “I regret and it makes me sad that Taylor had that reaction to the deal,” he said in 2021. “I don’t know what story she was told. I asked for her to sit down with me several times, but she refused.” Swift says that none of that is true, but it doesn’t really matter at this point. Braun’s reputation has never been worse.


Suge Knight addresses the 1995 Source Awards

In August 1995, Suge Knight took the stage at the Source Awards to accept the award for Motion Picture Soundtrack of the Year alongside Danny Boy for their work on the soundtrack to Above the Rim. “Any artist out there that wants to be an artist or stay a star — and don’t want to worry about an executive producer trying to be all the videos, all on the records, dancing — come to Death Row.” This was a direct shot at Puff Daddy for his work with the Notorious B.I.G. It was also the start of the East Coast/West Coast rap war that some people feel indirectly led to the deaths of Tupac Shakur and Biggie by inflaming tensions between the two camps. Knight did many worse things in his life than this quick moment onstage, but none had consequences quite as tragically awful. 


The Beach Boys skip the Monterey Pop fest

The Monterey Pop Festival was designed to showcase exciting new acts like the Who, the Jimi Hendrix Experience, Grateful Dead, the Mamas & the Papas, and Big Brother and the Holding Company. Brian Wilson served on the board of the festival, and the Beach Boys were booked to play on the second evening. It seemed to make a lot of sense since they were the quintessential California band and “Good Vibrations” had just hit the previous year. But they were in the middle of a very difficult time due to Brian’s deteriorating mental state, his failure to complete his ambitious Smile project earlier in the year, and Carl Wilson’s battle with the U.S. government over the Vietnam War draft. They’ve given many excuses over the years as to why they pulled out of Monterey Pop at the last minute, but fear they’d look lame alongside the hip, new bands was certainly a big part of it. In retrospect, the decision was a major turning point in their career.They’d go on to make plenty of great music, but they weren’t ever really part of the rock mainstream again.


David Bowie sort of suggests he’s cool with Nazis

Cocaine is one hell of a drug. The white powder is responsible for a great many bad decisions in rock history, and led to epic disasters like the 1997 Oasis LP, Be Here Now, and much of Elton John’s Eighties output. David Bowie somehow thrived on the drug, and it fueled his 1976 masterpiece Station to Station. But it took a tremendous toll on his mental health, since he was staying awake for days on end. His unique sleep schedule may have been one reason he offered up this notorious gem to a Playboy interviewer in 1976. “I believe very strongly in fascism,” he said. “Adolf Hitler was one of the first rock stars.” Right around this time, he was also photographed giving what appeared to be a Nazi salute at London’s Victoria Station. Bowie has denied this, of course, and it does seem like Salutegate was simply an unfortunately-timed photograph of a wave to fans, but it added up to some very toxic press. Here are some lessons: Don’t do cocaine, don’t publicly pontificate about the glories of fascism, and don’t wave to fans in a way that looks anything like a “Heil Hitler” salute. It’s just never a good look.


<strong>The Bee Gees and Peter Frampton make a film version of ‘Sgt. Pepper’s Lonely Hearts Club Band’</strong>

There were no bigger music acts on the planet in 1978 than the Bee Gees and Peter Frampton. Their latest albums, Frampton Comes Alive! and the soundtrack to Saturday Night Fever, sold a combined 10 zillion copies and made them into stadium-caliber superstars. For their next act, they decided to team up for the jukebox-musical monstrosity Sgt. Pepper’s Lonely Hearts Club Band, alongside Steve Martin, George Burns, Alice Cooper, Aerosmith, Donald Pleasence, and Sandy Farina. Directed by Michael Schultz, it takes the music of the Beatles and turns it into a psychedelic fever dream mixed with a Donny & Marie-style Seventies variety show. “Kids today don’t know the Beatles’ Sgt. Pepper,” Robin Gibb said at the time. “When ours comes out it will be, in effect, as if theirs never existed.” Um, nope. In fact, it ended up being one of the biggest flops in movie history up to that time, and the Bee Gees and Frampton were severely hobbled by its failure.


Metallica takes on own fans over Napster

Metallica weren’t wrong to see Napster as an existential threat to the record industry as it had existed up until that point in time. They weren’t wrong to be horrified that their 2000 song “I Disappear” leaked onto the file-sharing platform before they were ready to release it. They weren’t wrong to be upset that fans were sharing their entire catalog for free. They weren’t even wrong to sue Napster. But in the eyes of many fans, they crossed a huge line when they delivered the names of over 30,000 Metallica fans to Napster and asked them to be banned by the service. The backlash was almost universal, and it dogged them for years. “Maybe not the smartest PR move of all time, but at least we won the argument,” Metallica drummer Lars Ulrich said years later. “Listen, as they say, that and a quarter will get me on the bus, but it seemed like a really good idea at the time.”


Ashlee Simpson plays ‘SNL’ when she probably should’ve called in sick

Ashlee Simpson’s career was exploding when she was booked on an October 2004 episode of Saturday Night Live as the musical guest, alongside host Jude Law. She delivered her kickoff song “Pieces of Me” without any issues, but when she came back for “Autobiography,” prerecorded vocal tracks from “Pieces of Me” began playing. A mortified Simpson briefly did a little jig before running offstage as the show cut to commercials. The moment went as viral as possible in those primitive days of social media, and everyone assumed Simpson was a Milli Vanilli-like fraud. Simpson has offered a number of explanations for why she decided to use a vocal track, including acid reflux. The world would never have known had SNL pressed play on the right song, but that fateful error hobbled her career in ways that reverberate to this day.


The Beatles: “We’re bigger than Jesus”

In February 1966, John Lennon was speaking to Maureen Cleave, a reporter for London newspaper The Evening Standard, when he began pontificating about religion. “Christianity will go,” he said. “It will vanish and shrink. I needn’t argue about that; I’m right and I’ll be proved right. We’re more popular than Jesus now; I don’t know which will go first – rock & roll or Christianity.” The comments didn’t provoke much of a stir in England, but things were very different in America once they crossed the Atlantic. Radio stations all across the South banned the Beatles’ music, and there was even an event in Waycross, Georgia, where Beatles records were burned in a bonfire. When the Fab Four came to America a few months later, they faced massive protests outside some of the shows and empty seats in some markets. It was a miserable time for the entire band, and they never toured again.


Garth Brooks becomes Chris Gaines

Country megastar Garth Brooks was at the peak of his fame in 1999 when he decided to confuse the living fuck out of his fans by taking on the persona of fictional Australian rock star Chris Gaines, complete with a mock episode of Behind the Music, a Don Was-produced LP of new songs, an awful wig and soul patch, and even the promise of a Gaines biopic. Brooks hosted Saturday Night Live as himself, with Gaines as the musical guest, which just meant he threw on a wig during the commercial break. The bizarre move was a seemingly clever way for Brooks to experiment with new sounds, and the single “Lost in You” was indeed a minor hit, but the album sold a tiny fraction of his previous ones, and the biopic never materialized. Country fans really, really love country music, and they worship Garth Brooks. Chris Gaines, however, they could live without. Brooks returned to his classic sound in 2001 with Scarecrow, but he never quite managed to regain the career momentum he had pre-Gaines.


The guys in CCR who aren’t John Fogerty want to start writing songs

Most rock bands would have been thrilled to have John Fogerty as a member. He’s not only a stellar vocalist and guitar player, but he’s a uniquely brilliant songwriter whose classic run of Sixties hits includes “Proud Mary,” “Fortunate Son,” “Bad Moon Rising,” and “Who’ll Stop the Rain.” But his bandmates Doug Clifford, Stu Cook, and Tom Fogerty were resentful of the attention he generated and that most people saw them as his mere support musicians. The tension caused Tom Fogerty to quit in 1971, and the next year John agreed to a democratic album where Clifford and Cook would be allowed to write and sing their own songs. The result was the disastrous Mardi Gras, which Rolling Stone writer Jon Landau described as, “the worst album I have ever heard from a major rock band.” It proves that democracy may be a great form of government, but it’s not always best for bands. The group split up not long after Mardi Gras came out.


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.”


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.”


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.”


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.


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.


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.


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.


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.


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.


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?”


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.