November 29, 2022 10:28AM

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

By ANDY GREENE

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

By late 1979, everyone from Rod Stewart to the Rolling Stones to Kiss had created enormous disco hits. The move may have alienated some of their original fans, but that hardly mattered when you have songs as big as “Miss You,” “I Was Made For Lovin’ You,” and “Da Ya Think I’m Sexy?” And so it’s easy to understand why Elton John, coming off a string of disappointing albums like A Single Man and Blue Moves, decided to team up with English producer Pete Bellotte and craft the disco LP Victim of Love. But it hit after the “Disco Sucks” backlash was in full force, and John made baffling choices on the LP, like turning Chuck Berry’s “Johnny B. Goode” into a dance track. Victim of Love was complete commercial bomb, and it wrapped up the most extraordinary decade of John’s career on a very sour note. “It didn’t do my career a lot of good,” John said, “but I don’t regret it.”

Glen Matock wasn’t just the bassist in the Sex Pistols, but also one of their key songwriters. Despite that, they fired him in early 1977 after months of tension between him and Johnny Rotten. The band could have survived and perhaps even thrived if they’d brought in a competent replacement capable of playing his parts and contributing to future songwriting sessions. Instead, they brought in a heroin addict that had no clue how to play the bass or write anything resembling a song. Sid Vicious may be an icon, but he didn’t do much in the band besides cause chaos and speed up the timeline of their inevitable breakup. “Maybe the chemistry would’ve sustained us to do another album if Matlock had hung around,” guitarist Steve Jones admitted in his memoir, Lonely Boy. “But it wasn’t in our destiny to have a progressive phase where we made a folk record and went on tour with Barclay James Harvest. The Sex Pistols were born to crash and burn, and that’s exactly what we did.”

The Grammys don’t have a great track record when it comes to picking the Best New Artist of any given year. The Beatles may have won in 1965, but they also gave it to the Starland Vocal Band in 1977 and to Debby Boone in 1978. Now let’s take a look at the nominees in 1979: the Cars, Elvis Costello, Toto, blues-rock guitarist Chris Rea, and disco duo A Taste of Honey, who topped the charts in 1978 with “Boogie Oogie Oogie.” The Grammys went with, of course, A Taste of Honey. We’re not knocking the group. “Boogie Oogie Oogie” is a fine song. But maybe, just maybe, the Cars or Elvis Costello deserved the award a little more.

Long before Maroon 5 frontman Adam Levine started sending cringe-inducing DMs to women on Instagram, we’d all seen many men ruin their marriage and careers over such acts. That didn’t stop him from writing horrifying notes like “Watching your ass jiggle on that table will permanently scar me” or “I may need to see the booty” to complete random women on Instagram. When they surfaced, the internet put aside all its differences to come together in making fun of him. “I used poor judgment in speaking with anyone other than my wife in any kind of flirtatious manner,” he wrote in a statement, “I did not have an affair, nevertheless, I crossed the line during a regrettable period in my life.” We have no idea how his wife feels about all this (she’s still with him and they’re often seen together in public), but the internet never forgets. He’ll be seeing jokes about “I need to see the booty” in his mentions until the end of Twitter.

By the end of the Sixties, Bob Dylan was so annoyed by a media that treated him as the “voice of a generation” and a fan base that saw him as a messiah that he decided to do something drastic. “I said, ‘Well, fuck it. I wish these people would just forget about me,’” he told Rolling Stone in 1984. “I wanna do something they can’t possibly like, they can’t relate to.” This led to Self Portrait, a double album of mainly cover songs he glooped up with strings, choirs, and horns. Greil Marcus spoke for many critics when he opened up his Rolling Stone review with the words, “What is this shit?” “The whole idea backfired,” Dylan said. “Because the album went out there, and the people said, ‘This ain’t what we want,’ and they got more resentful.”

Yes were not in a good place when the Seventies ticked over into the Eighties. “Prog rock was so wonderfully out of fashion,” keyboardist Rick Wakeman told Rolling Stone in 2019. “It was the equivalent of turning up at the Vatican and being like, ‘Can we put up some condom machines?’” They attempted to cut a new record in Paris, but the sessions went so poorly that Wakeman and lead singer Jon Anderson wound up leaving the band. That’s when their manager had the idea of simply folding Trevor Horn and Geoff Downes of New Wave band the Buggles, who he also managed, into Yes. They cut the LP Drama and tried to tour without making a big fuss about the whole “our singer and keyboardist are no longer in the band, but here’s the ‘Video Killed the Radio Star’ guys instead” thing. “[Bassist] Chris [Squire] told me later it was a nightmare,” Wakeman said. “He said, ‘We’d walk onstage and people would cheer and be like, “Hey, Steve! Hey, Chris! Hey, Alan! Who the hell is that?’ They had this fat, dumpy guy at the front singing and Geoff Downes. They’d be like, ‘That’s not Jon! That’s not Rick!’ Chris said it was an absolute nightmare from start to finish.” The group broke up when the tour ended. When they reformed in 1983, Jon Anderson was back in front.

Janet Jackson’s career was dealt a major blow in 2004, when her right breast was exposed at the Super Bowl halftime show in front of a global audience of countless millions. In the aftermath, her music was blacklisted by radio stations and her new LP Damita Jo suffered as a result. It was the start of a long free fall for Jackson after two decades of total pop dominance. The problem is she wasn’t the one that exposed her breast. Justin Timberlake did that when he ripped off her top. His true intentions behind the move will never be known. He says he thought she was wearing a bikini, while others feel it was a publicity stunt of some sort. Either way, his career continued to move seamlessly ahead. He was even invited back to perform at the Super Bowl halftime show in 2018. Janet has yet to be asked back.

As the ticket on-sales for Bruce Springsteen and Taylor Swift proved this year, something is deeply wrong with Ticketmaster. The ticket retailer’s use of dynamic pricing meant that Springsteen fans saw prices quadruple right in front of their eyes, and the whole system simply melted down when Swift put her tour on sale. This is partially because Ticketmaster has not found a way to effectively figure out how to deal with the ticket bots that jam their network and take all the best seats. They’ve also joined the scalpers at their own game by allowing resellers – who often use bots – to offer seats on the Ticketmaster platform for wildly inflated prices. Ticketmaster, of course, takes a cut each time the ticket is sold. The whole system is hopelessly broken. By this point, we’d be better off going back to 1985 when everyone just lined up at Tower Records.

In 1967, the Monkees were as big as the Stones and the Beatles and anyone else in pop music. They had a foolproof formula where their TV show promoted their music, and their music turned around and promoted the TV show. It led to huge hits like “I’m a Believer,” “Daydream Believer,” and “Pleasant Valley Sunday.” But the TV show was cartoonish and aimed almost exclusively at children. When it came time to make a movie in 1968, they teamed up with a pre-famous Jack Nicholson, got incredibly stoned, and cooked up the incomprehensibly psychedelic Head. All four Monkees die in the first scene, and it only gets stranger from there. The music is absolutely stellar, perhaps the best stuff they ever did, but kids bought tickets expecting to see something like the zany TV show — and adults stayed away completely. It was an absolute fiasco that marked the beginning of the end of the band.

Prince had every right to be frustrated with his Warner Bros. Records label in 1993. He was recording music at a furious clip, and the company simply wasn’t releasing it. He also felt the contract he signed with the label back in 1977 was unfair and essentially made him a “slave.” He decided the best way to fire back was to change his name to an unpronounceable symbol, thinking it would somehow nullify his contract. That’s not what happened. Warner Bros. wound up sending thousands of computer discs containing the symbol to media outlets so they could print his new name. They also referred to him as “the Artist Formerly Known as Prince.” The whole gambit confused his fans and did little to help with his flagging record sales. When his deal with Warner expired in 1996, he changed his name back.

When Tricky Stewart co-wrote “Umbrella” in 2007, he imagined Britney Spears singing it. They had worked together on her 2003 Madonna duet, “Me Against the Music.” But Spears was battling a lot of personal demons when the song was sent over to her team, and they decided it wasn’t worth recording. “Umbrella” ultimately made its way over to Def Jam and a young artist named Rihanna. It hit Number 1 all over the world and turned the singer into one of the biggest stars of her era. If Britney had recorded “Umbrella,” the last 15 years of pop-music history might have unfolded very differently.

On Weezer’s 2008 hit “Pork and Beans,” Rivers Cuomo complains about the pressure aging musicians faced to remain current. “Timbaland knows the way to reach the top of the charts,” he sang. “Maybe if I work with him, I can perfect the art.” Cuomo wasn’t serious and had no real intention of working with Timbaland, but Chris Cornell actually went through with it on his 2009 solo LP, Scream. It was seemingly a chance to appeal to both fans of hip-hop and Nineties rock, but it turned out that neither one of those audiences had the slightest interest in hearing this thing. The album was brutalized by critics, the singles all bombed, and within two years Cornell was reuniting with Soundgarden and acting like the whole thing never even happened.

When Roger Waters parted ways with Pink Floyd in 1985, he thought he was dooming the band forever. After all, he’d been their primary songwriter and creative force ever since Syd Barrett left the band in 1968. He figured they’d simply fold up shop and all their fans would follow him into his solo career. What he didn’t realize was that Pink Floyd was a significantly more famous “brand” than Roger Waters, and that the band’s remaining members could continue packing stadiums and even scoring new hit songs with the help of outside writers. When they both hit the road in 1987, Waters faced oceans of empty seats in many markets while Floyd were playing multiple nights in football stadiums. It drove him absolutely insane. “If one of us was going to be called Pink Floyd, it’s me,” he snarled to Rolling Stone in 1987. “That’s my pig up there. That’s my plane crashing … it’s their dry ice.” It would be more than another decade before Waters even attempted another tour, and by that point Pink Floyd were no longer a going concern. It was only then that he was able to finally launch himself as an arena headliner.

The Stones Roses self-titled 1989 debut LP is a flawless masterpiece set the stage for the entire Nineties Brit-pop movement. Songs like “I Wanna Be Adored,” “Fools Gold,” and “I Am the Resurrection” are a perfect fusion of dance, rock, and psychedelia that haven’t aged a day in the past three decades. These songs won over England and could have crossed over the Atlantic to America had they put in a little effort and worked the U.S. club scene. That’s not what happened though. The band instead got bogged down in a massive legal battle with their label, started squabbling internally, and took five endless years to cut their second record, 1994’s The Second Coming. As the title suggests, they felt they were Jesus at this point. The public didn’t agree. They’d already moved onto Oasis and Blur. The Stone Roses broke up in 1996 and wouldn’t reform until 2011.

When David Geffen signed Neil Young to a record deal in the early Eighties, he presumed he’d keep pumping out crowd-pleasing albums along the lines of Rust Never Sleeps and Comes a Time for the foreseeable future. But this was a very new musical era, and Young was distracted by the needs of his young son Ben, who was born with cerebral palsy. He started recording songs with a vocoder that distorted the sound of his own voice in an attempt to convey what it’s like communicating with a loved one that can’t comprehend language. The result was the Trans, an experimental LP that had more in common with Kraftwerk than anything Young had done up to that point in his career. It sold very poorly, but an undeterred Young kept releasing genre albums like the rockabilly-inspired Everybody’s Rockin’ and the country collection Old Ways. This enraged Geffen to the point that he actually filed a lawsuit against Young for making “unrepresentative” music. It led to a ridiculous legal battle that Geffen later acknowledged was a heinous mistake. If you sign Neil Young, you just gotta let him be Neil Young.

At the height of the hair-metal movement, Jane’s Addiction rose out of the Los Angeles club scene and gave hope to fans that rock & roll could say more than “Talk Dirty To Me.” Their success allowed groups like Nirvana, Pearl Jam, and Soundgarden to emerge onto the national scene, and they started the original Lollapalooza to give these bands an even bigger platform. But after recording just two proper albums, right at the moment that alt-rock started making real money, the group called it quits. “I was thinking about why exactly I would do something like that,” frontman Perry Farrell told Rolling Stone this year. “Looking back at it now, it seems like [one of] the dumber moves I’ve ever made in my life. We were on top of the world.” The band reunited in 1997, but they never regained the momentum they lost from the original split.

For one brief moment in 2013, Robin Thicke was on top of the world. After a decade of creating R&B-tinged tunes that never found more than a cult audience, he finally had a genuine monster hit with “Blurred Lines,” thanks to a risqué video featuring Emily Ratajkowski, Elle Evans, and Jessi M’Bengue. But a major backlash quickly hit since the song seemed to suggest there were “blurred lines” between consensual and nonconsensual sexual encounters. It was also the subject of a lawsuit by the Marvin Gaye estate, which felt it ripped off Gaye’s 1977 song “Got to Give It Up.” Throughout all of this, Thicke was using drugs and cheating on his wife, Paula Patton. When she filed for divorce in 2014, he tried to win her back by calling his next album Paula and writing song after song about his undying devotion to her. It’s a cringe-fest from start to finish that critics shredded and fans ignored. It also didn’t work. The divorce was finalized in 2015. He hasn’t had anything resembling a hit since Paula came and went, and he’s now a judge on The Masked Singer.

By the dawn of the Eighties, Kiss were tired of being seen as a band for children or stunted adults. They’d had huge success in recent years with their disco song “I Was Made For Lovin’ You,” but there were also epic flops, like their TV movie Kiss Meets the Phantom of the Park and the four solo albums they released on the same day in 1978. Bob Ezrin, the producer of their most beloved albums, had just helped Pink Floyd craft The Wall, and they decided to bring him back into the fold to create something just as ambitious. The result was Music From the Elder, a disjointed, confused concept record that adds a choir and an orchestra to the Kiss sound with predictably awful consequences. The plot involves a character known only as The Boy who joins forces with a wise guru named Morpheus to battle a shadowy group of villains at some indeterminate point in the future. (This may sound like The Matrix, but trust us when we say that would give this thing way too much credit.) It’s so astonishingly bad that the group didn’t even tour behind it, and they dropped all plans to take another page out of the Pink Floyd playbook by making a movie that tied into it. “That was the one time I would say that Kiss succumbed to the critics,” Gene Simmons said many years later. “We wanted a critical success. And we lost our minds.”

The New York Dolls self-titled 1973 debut didn’t just set the stage for the entire punk-rock revolution that followed, it was also a street-glam masterpiece that only improves with age. There isn’t a weak song on the whole thing. At the time, however, it was a massive commercial disappointment that peaked at Number 116. In a radical attempt to change up their image and generate attention after their 1974 follow-up fared even worse, they hired Malcolm McLaren and agreed with his crazy scheme to dress in red leather and play in front of the red flag emblazoned with a hammer and sickle. The provocation was meant to get them press attention, but it was mostly just ignored. The group broke up months later. Not long after, McLaren assembled the Sex Pistols and proved that basing your music on French situationism, not communism, was a much surer way to rocket up the charts.

Phil Spector produced some of the best songs of the early Sixties, and he had a major comeback in the early Seventies when the Beatles asked him to salvage their Let It Be project. This led to work on John Lennon’s Imagine and Geroge Harrison’s All Things Must Pass. You can’t blame Leonard Cohen for asking Spector to produce his 1977 LP, Death of a Ladies Man. Cohen was a decade into his career and yet to see an album rise higher than Number 63 on the Billboard Album Chart. Why not try out the most revered producer in rock history? What he didn’t realize was that Spector’s mental state had deteriorated to a frightening point, and he was then a paranoid, volatile, gun-toting maniac. “There were lots of guns around in the studio and lots of liquor,” Cohen said in 2001, “a somewhat dangerous atmosphere.” They managed to record a few genuinely great songs like “Memories” and “True Love Leaves No Traces,” but Spector absconded with the tapes at one point and simply finished the album on his own, using rough vocals that Cohen planned on perfecting at a later date. The result is a very compromised album that didn’t satisfy Cohen or his fans. It didn’t even dent the Billboard 200.

When rock historians look back at 1992, they often focus on the rise of grunge bands like Pearl Jam and Nirvana. But if you actually took a time machine back to the year and turned on MTV or the radio, you’d be bombarded with the Spin Doctors. Their singles “Two Princes,” “Little Miss Can’t Be Wrong,” and “Jimmy Olsen’s Blues” were inescapable that year. They all came from the group’s debut LP, Pocket Full of Kryptonite. It seemed like the start of a very long and promising career. But when it came time to launch their 1994 follow-up LP, Turn It Upside Down, they kicked things off with the single “Cleopatra’s Cat.” The song had a limp, lifeless jazz-funk groove and lacked anything resembling a memorable hook. But that was just the start. Singer Chris Baron literally scatted his vocals, which were packed with references to Mark Antony, Brutus, and centurions that went completely over the head of the Doctors’ teenage audience; MTV dropped the video within a day or two. “It was the wrong move,” Barron tweeted in 2022. “I was uneasy about it at the time. Our management thought it would be sort of a slow burn and we would get more mileage out of the record.” Good managing!

When Axl Rose let go of every single member of Guns N’ Roses in the mid-Nineties, he had a short window of time to prove the group could still move forward as a creative entity and not just a watered-down oldies act. If they produced another album even near the quality of Appetite for Destruction or even Use Your Illusion I and II, the haters would have been silenced and they could have marched forward. Instead, Axl and a rotating crew of new gunners spent nearly 15 years laboring away at Chinese Democracy, burning untold millions of dollars and an incalculable amount of fan goodwill in the process. The band’s label Geffen even offered Rose a million-dollar bonus to finish it by 1999, a deadline he blew by nine years. When it finally came out in 2008, few fans were still paying attention. A little patience is one thing. Nearly 20 years is something else.

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Van Halen was already fighting gravity in the mid-Nineties, after their LP Balance disappointed commercially and MTV essentially froze out every band from their era. The best way forward at that point was to either reunite with David Lee Roth for a tour or go into the studio with Sammy Hagar and make another killer album. They choose option C: Fire Sammy Hagar, tease a reunion with Roth at the MTV Video Music Awards, and then bring in former Extreme singer Gary Cherone to front the band for an underwhelming album and tour. “It was a bad time to be making that move,” Hagar told Rolling Stone earlier this year. “That was the biggest mistake the band has ever made.”

Elvis Presley made a handful of decent films, most notably Viva Las Vegas, King Creole, Blue Hawaii, and Jailhouse Rock. But the vast majority of them are pure schlock like Harum Scarum and Clambake — and he didn’t make a single one that has endured through the generations. That could have been different had Elvis appeared alongside Barbra Streisand in the 1976 remake of A Star Is Born. Presley was Streisand’s first choice for the role, and they met in person to discuss it. But Colonel Tom Parker insisted that Elvis receive top billing and an exorbitant salary. Parker also hated the script since it presented his character as washed up. This was more hassle than the producers could handle, and they wound up casting Kris Kristofferson instead. An acclaimed movie could have been a major comeback vehicle for Elvis, and it could have helped him right the course of his life during a very difficult period. Sadly, that’s not what happened.

Woodstock is the most famous festival in rock history, and acts like the Who, Santana, CSNY, and Joe Cocker benefited enormously by their association with it. Those performers all signed off on the contract to appear in the Woodstock movie, which was seen by a far broader audience than the hippies that schlepped to Bethel Woods, New York. “Mississippi Queen” rockers Mountain, however, didn’t agree to be in the movie despite playing an explosive set on the second day of the festival, sandwiched between Canned Heat and the Grateful Dead. “I don’t know what happened with my manager at the time, he probably didn’t get enough money,” Mountain frontman Leslie West said in 2015. “Who knows?” And who knows what could have happened to Mountain in the Seventies and beyond had they been in the movie.

It’s easy to understand why Warner Bros. felt that R.E.M. deserved an $80 million record deal in 1996 that called on them to record five more albums for the label. They were coming off a ridiculously successful run of albums that featured hits like “Losing My Religion,” “Everybody Hurts,” and “Man on the Moon,” and had been one of the most critically adored bands in the world for the past 15 years. This was the pinnacle of big money deals for icons like Janet Jackson and Metallica, and labels were swimming in profit thanks to $20 compact discs. But Warner Bros. didn’t know that founding drummer Bill Berry was about to leave the band. The company didn’t know their 1998 LP, Up, would be a commercial dud, and that the next albums would fare even worse. They didn’t know that Napster was going to hit within a few years and totally destroy their CD-based business model. They thought that 1996 was going to last forever, and it cost them a fortune. More than 25 years later, this is still regarded by many as the worst record deal of all time.

Dee Dee Ramone is an excellent bass player, lyricist, and songwriter. But he’s a very, very bad rapper. For proof, check out his 1987 single “Funky Man,” which contains lyrical gems like “I play the bass in a punk rock band/Been to all the world/Even to Japan/And nothing can surprise me man/I’ve seen it all/I had a ball/Someone should make a Dee Dee doll.” His Ramones bandmates were mortified when he began showing up to shows in full hip-hop regalia, and even less encouraging when he decided to record an entire rap album in 1989 under the moniker Dee Dee King. He quit the Ramones that same year. After the album fell down a commercial and critical mineshaft, he returned to punk rock.

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.

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 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.

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 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.

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.

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 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’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.

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.

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.

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.

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.”

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 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.”

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.

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.

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.

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.

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.

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.

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 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.

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