There’s only one rivalry that I was required by law to write about in this book, and that rivalry is the Notorious B.I.G. vs. Tupac Shakur. (Or, if you happen to live on the coast, Tupac vs. Biggie. Tupac eternally rules the West.) I suspect that many readers will turn immediately to this chapter, as Biggie vs. Tupac is the most obvious example of my thesis. It might also make you want to put this book down immediately and never think about pop rivalries ever again. Contemplating Biggie vs. Tupac tends to make obsessing about pop rivalries seem silly to the point of recklessness. It stops being fun once you realize that taking this stuff too seriously can result in people getting killed.

You could call Biggie vs. Tupac the greatest rivalry in pop history, so long as “greatest” is understood to mean “saddest” and “most tragic.” I watched it unfold along with the rest of my generation; in retrospect, Biggie vs. Tupac stands as the logical extreme of the culture’s obsession with authenticity in the ’90s, even more than Kurt Cobain’s suicide. A suicide requires only the act of one person; Biggie vs. Tupac was a conspiracy that will probably never be fully unraveled.

It was predicated almost entirely on misinterpreted statements and misconstrued incidents: here were two hip-hop superstars portrayed in the media as mortal enemies, largely because they were situated on opposing coasts in the nation’s largest cities. One was a svelte, conventionally handsome, deeply philosophical Bob Marley figure, and the other was a fat, unconventionally handsome, persuasively suave James Bond–style hedonist. Because they looked the part of rivals, Biggie and Tupac were encouraged to play up their public animosities and reinforce their warring personas. Incredibly, horrifically, inevitably, they both wound up murdered within six months of each other. But they’ve lived on as bookending archetypes that practically every major rapper has emulated since—Biggie is the methodical fatalist determined to enjoy his empire in spite of mounting paranoia, and Tupac is the freewheeling messianic figure impulsively (knowingly?) creating his life’s work in a limited time frame. These are characters that other artists reboot again and again.

It’s impossible to properly explain to a person who wasn’t alive at the time how and why this happened. The Internet has made us accustomed to perceiving conflict as both unreal and omnipresent. Flame wars occur now as a matter of course, and they typically end with a barely acknowledged whimper. Biggie vs. Tupac wasn’t like that. It was very real and lasting in the most brutal way imaginable.

Nobody will ever take a pop-star rivalry that seriously ever again. Biggie vs. Tupac endures as a line of demarcation that cannot be crossed. This wasn’t immediately apparent: the first Beef documentary, released in 2003, ends with an ominous overview of the conflict between 50 Cent and Ja Rule, which seemed to be on the verge of a Biggie vs. Tupac–type reckoning. Outside of Eminem, Ja Rule and 50 Cent were probably the biggest rappers on the planet in the early aughts, and there were some minor parallels between their rivalry and that of Biggie and Tupac. Like Tupac, 50 Cent was famous for being shot numerous times and surviving; meanwhile, in Beef, 50 chides Ja Rule for wanting to be like Tupac while also expressing disbelief that anybody would want to be like Ja Rule.

The 50 Cent–Ja Rule feud did turn violent on a few occasions—50 Cent supposedly clocked Ja Rule in Atlanta in 2000, and soon afterward, Ja Rule’s associate Black Child claimed responsibility (and self-defense) for stabbing 50 Cent at a New York recording studio. But for the most part 50 Cent vs. Ja Rule was settled on the charts, and 50 Cent destroyed his antagonist. It got so bad for Ja Rule that he was reduced to proposing a détente moderated by Louis Farrakhan on MTV that was to take place right before the release of his album Blood in My Eye. It was part publicity stunt and part capitulation to 50 Cent’s enormous popularity in the wake of his 2002 debut LP, Get Rich or Die Tryin’. By virtue of his power in the market and the support of fellow superstars such as Eminem, Dr. Dre, and DMX, 50 Cent had neutralized Ja Rule via a bloodless takeover.

For all the hip-hop feuds that followed—enough to justify two other Beef films and a TV series—they never approached Biggie vs. Tupac in terms of stature or body count. It’s been said that John Belushi’s death was a wake-up call for other movie stars enjoying recreational speedballs in the early ’80s. I suspect a similar case can be made for Biggie vs. Tupac. It’s the ultimate example of “taking it too far”: on some level, Biggie vs. Tupac has probably saved countless lives, and not just those of rappers.

Everybody knows that Biggie vs. Tupac ended in gunfire, but the rivalry inadvertently began with gunfire, too. To rehash a well-worn story: In 1994, Tupac was robbed and shot several times in the lobby of Quad Recording Studios, in Manhattan. Shortly after the attack, Biggie released “Who Shot Ya?” as the B side to his single “Big Poppa.” Biggie and Sean “Puffy” Combs happened to be recording at Quad when Tupac was shot, and it’s long been theorized that they knew about the attack in advance, though Biggie and Puffy made a point of going on MTV to deny it. When Tupac heard “Who Shot Ya?” he interpreted the track as a taunt, even though it had supposedly been recorded before the shooting. (Biggie’s insistence on performing the song live after Tupac was shot didn’t discourage this interpretation.) “Who Shot Ya?” compelled Tupac to implicate Biggie and the owners of Biggie’s record label, Bad Boy—Combs and Andre Harrell—for ordering the hit.

Let’s pause for a moment. It’s crazy that this issue, at this specific moment, wasn’t nipped in the bud. If representatives from Biggie’s and Tupac’s camps had somehow been able to meet and hash out the beef, it seems possible (if not likely) that things would’ve turned out differently later on. Biggie vs. Tupac might’ve been a funny footnote discussed on I Love the ’90s TV specials. Instead, almost a year later, Tupac became an associate of Suge Knight, who posted $1.4 million in bail in order to spring Tupac from a Florida prison while Tupac’s sexual assault case was on appeal.

A former college football player who played two games in the pros as a replacement player for the Los Angeles Rams during the NFL’s strike-shortened 1987 season, Knight subsequently entered the music business as a promoter and bodyguard for artists such as Bobby Brown. Knight already had a reputation as a hothead—he was arrested twice during a single month in ’87, once for hitting his girlfriend and once for shooting a man three times while attempting to steal the man’s car. In 1989 Knight formed his own music-publishing company and made his first big score when he secured a percentage of Vanilla Ice’s hit “Ice Ice Baby” for his client Mario Johnson, the song’s cowriter. (It’s part of hip-hop lore that Knight threatened to throw Vanilla Ice off a balcony, though the involved parties deny it.) Two years later, Knight established Death Row Records with ex-N.W.A. member Dr. Dre, vowing that it would become the Motown of the ’90s. But Knight never fully left his violent past behind him.

When you start associating with Suge Knight, no matter the circumstances, you have reached the point of no return. Such was the case for Tupac.

Knight had his own beef with Combs. Knight’s friend Jake Robles had been fatally shot at a party in Atlanta hosted by Jermaine Dupri, and Knight blamed Puffy. It’s not clear to what degree this influenced Tupac, but it certainly didn’t improve the situation with Biggie. This was the setup for Knight’s infamous provocation of Combs and the East Coast rap elite at the 1995 Source Awards at Madison Square Garden’s Paramount Theater, which stoked the flames publicly.

“To all you artists out there who don’t wanna be on a record label where the executive producer’s all up in the videos, all on the records, dancin’, then come to Death Row!” Knight said from the stage, obviously referring to Puffy, in the town where Bad Boy was headquartered. It was practically an official declaration of war.

In his songs, Tupac took repeated shots at Biggie, including the claim in “Hit ’Em Up” that he slept with Biggie’s wife, Faith Evans. Some listeners believed Biggie responded in “Long Kiss Goodnight”—the lines “Slugs hit your chest, tapped the spine, flatline / Heard through the grapevine you got fucked four times” seem suspiciously pertinent—but it was never confirmed as an official diss.

The primary reason I didn’t want to write about Biggie vs. Tupac is that there is so much we still don’t know about how they died or what their true intentions were in going after each other. For instance, it’s still unclear whether their murders even resulted from their rivalry. It seems likely that they did, but the murders have never been solved or properly explained. The 2011 book Murder Rap, written by former LAPD detective Greg Kading, fingered Combs for commissioning the murders of Shakur and Knight, then accused Knight of paying for Biggie’s murder. Both the presumed triggermen were gang members who were later shot to death—Tupac’s alleged killer, Orlando Anderson, died outside a Compton record store in 1998, and Biggie’s supposed murderer, Wardell “Poochie” Fouse, was killed in 2003 after multiple shots were fired into his back while he rode a motorcycle through Compton. This goes beyond the usual pop-star feud. This is real-life Keyser Söze stuff.

As the murders of Biggie and Tupac drift deeper into history, it’s increasingly difficult to talk about them as real, tangible events. The mystery has only deepened; conspiracy theories about cover-ups and crooked cops on both sides of the investigation have made the truth more elusive, if not obscured it completely. It’s been theorized that Knight engineered Tupac’s death because he was upset that Tupac was about to leave Death Row. It’s been speculated that several LAPD officers—including Rafael Perez, David Mack, and Nino Durden, who were named in a wrongful death lawsuit filed by Biggie’s family in 2007 and dismissed from the force three years later—were enlisted by Knight to kill Biggie. In 2002, a Pulitzer Prize–winning reporter for the Los Angeles Times named Chuck Philips reported that Biggie visited several Crips gang members in Las Vegas on the night Tupac was shot, essentially overseeing the murder, even insisting that they use his gun. Six years later, Philips was forced to retract an article that advanced a theory about Biggie and Combs having prior knowledge of Tupac’s ’94 shooting, which had originally sparked the rivalry, when it was revealed that his reporting relied partly on forged FBI documents given to him.

Twenty years later, parsing all this is like trying to prove or disprove that JFK was really killed by Lee Harvey Oswald. Biggie vs. Tupac is so fucked-up it makes thinking like Oliver Stone seem reasonable.

What makes Biggie vs. Tupac a defining pop rivalry isn’t so much what actually happened but what we imagine happened. This applies to the media coverage of the rivalry, which arguably made the situation worse by intensifying the burgeoning mythology. But it also derives from the music and the way it was contextualized after both men were gone. Biggie and Tupac capped their careers by releasing brilliant double albums—Life After Death for Biggie, All Eyez on Me for Tupac—that balance party jams with relentless paranoia. (I suppose you could argue that Shakur’s true career capper is The Don Killuminati: The 7 Day Theory, which was recorded shortly before he was murdered and released under the stage name Makaveli two months after his death. But I prefer to go with the last record that Shakur actually signed off on.) It’s trite and borderline offensive to suggest that Biggie and Tupac made art that predicted their own demise: first and foremost, they were entertainers, and they constructed entertaining personas that were electric in the context of plush production and magnetic lyrical swagger. Those albums don’t play in the manner of Nirvana’s MTV Unplugged in New York, on which Kurt Cobain basically plays at his own wake four months early. Biggie and Tupac sound alive—powerfully, vividly, stubbornly—on their records, regardless of their preoccupation with their own mortality.

Biggie and Tupac were unlucky in that the fanciful worlds they brought to life on their records came true in real life. This typically isn’t an occupational hazard for musicians—Marilyn Manson has been singing about self-destructing on bad drugs and kinky sex for more than twenty years, yet he’s lived to see middle age and now looks strikingly like Nicolas Cage rolled in baking flour. Because Biggie and Tupac died in such a violent, public, and unfathomable manner, it was natural for listeners to merge the fantasy of their songs with the reality of their star-crossed lives.

Life After Death ends with a song called “You’re Nobody (Til Somebody Kills You),” a takeoff on the old crooner standard “You’re Nobody till Somebody Loves You.” All Eyez on Me concludes with a song with a similarly eerie title, “Heaven Ain’t Hard 2 Find.” Neither song is as prescient as it might seem. The lyrics of “You’re Nobody” read like an action-movie screenplay, vividly describing “gun-testing,” “coke-measuring,” and “spending chips at Manny’s,” the steak-house chain. It’s true that Biggie spent time in prison before he was famous—he was pinched in 1991 for dealing crack cocaine in North Carolina and served nine months. Before that, he was sentenced to five years’ probation in 1990 on weapons charges. But Biggie was hardly a kingpin. Very stupid people will hear “You’re Nobody” as scary, first-person nihilism, but it’s really just a young guy describing some incredibly cool shit he probably saw in a movie once. (Biggie refers to himself as Nicky Tarantino, alluding to Joe Pesci’s character from Casino and, presumably, Quentin Tarantino.)

The last song on All Eyez on Me is romantic in a different way—in “Heaven Ain’t Hard 2 Find,” Tupac is at his sweetest, asking, “Are you afraid of a thug? / And have you ever made love / With candles and bubbles sipping in your tub?” Does a man who expects to die talk about having sex in bathtubs? Isn’t sex in a bathtub the very essence of life, especially when you’re twenty-five and on top of the world?

  

As I write this, Justin Bieber is the most controversial pop star alive. Nobody seems remotely close. It’s possible to make a case for Miley Cyrus, but she’s a cultural provocateur. Outraging the public is supposed to be what her art is about; taking the bait integrates the listener into her music and iconography, as offended observers are as vital to Cyrus’s aesthetic as voluptuous backup dancers or Terry Richardson’s skeezy music videos are.

Bieber provokes the public with his personal life. I’m reluctant to delve into Bieber’s arrest record, as the statistics will be instantly outdated as soon as this book comes out. Every other week, Bieber is detained for doing something stupid. He drives recklessly and commits acts of vandalism like you and I take out the garbage.

Bieber has entered that rare zone for famous people where the public expects you to behave outrageously, which therefore empowers you to make even worse decisions. (The king of this zone is Charles Barkley, who could solicit oral sex from a prostitute during TNT’s pregame NBA show and receive only mild admonishment from Ernie Johnson.) Bieber once was caught on multiple videos using the n word, and it not only didn’t end his career, it was also forgotten after about a week. If I had to guess what Bieber is doing at this very moment, I would bet that he is smoking weed in the parking lot of a Carl’s Jr. If there’s a Carl’s Jr. in your town, call the police and ask that they do a quick sweep of the premises, just in case.

The consensus view of Bieber is that he is yet another victim of “too much too soon.” Becoming a superstar when he was a teenager who resembled a fetus has fixed him in perpetual adolescence. Bieber’s world has been set up to cater to his every whim, ensuring that his life will only get worse in ensuing years. Eventually he will succeed in alienating the public, damning him to a long life of irrelevance and the collateral damage of never having had a proper childhood.

If Bieber is headed down a bad road, he’s probably not pointed toward the worst destination. No matter how fucked-up he seems to be in terms of his interpersonal development, I doubt that Justin Bieber will die prematurely.

This might sound weird to point out, but pop stars don’t die like they used to. In the ’60s, ’70s, ’80s, and ’90s, pop stars died all the time. Many of the most popular and important artists of the twentieth century died in their prime: Elvis Presley, Buddy Holly, Otis Redding, Jimi Hendrix, Janis Joplin, Gram Parsons, Nick Drake, Cass Elliot, Jim Croce, Marc Bolan, Bob Marley, and Karen Carpenter all perished at an early age. Many of the most iconic bands had at least one member die before the age of forty: the Beatles, the Rolling Stones, Led Zeppelin, the Who, the Beach Boys, the Doors, the Allman Brothers Band, Lynyrd Skynyrd, AC/DC, the Sex Pistols, Joy Division, and the Minutemen all had significant casualties. During this time, so many famous musicians died from choking on their own vomit that it became one of the best jokes in This Is Spinal Tap. For a while it was relatively common for pop stars to be shot to death by people who presumably liked them: John Lennon was murdered by an obsessive fan, and Marvin Gaye was cut down by his own father.

In the early ’90s, major pop stars were still dying young at a steady clip. They died in plane crashes (Stevie Ray Vaughan), from overdoses (Johnny Thunders and Def Leppard’s Steve Clark), from AIDS (Freddie Mercury), from self-inflicted gunshot wounds (Kurt Cobain), from fan-inflicted gunshot wounds (Selena), and from living extremely gross lifestyles (GG Allin). Then, after the deaths of Biggie and Tupac, something changed. The death rate among iconic musical figures suddenly declined dramatically.

Below is a list of noteworthy pop-star deaths since Biggie vs. Tupac. It is not a list of every pop-star death—I haven’t included musicians who died of natural causes at an advanced age (such as Johnny Cash and James Brown) or who passed on in middle age from relatively common ailments (such as Warren Zevon and Levon Helm). I also tried to limit this list to noteworthy deaths—no disrespect to the bassist of Blues Traveler or the guy who designed the awesome soundscapes for the Mars Volta’s first record, but I’m only counting legends who died before their time.

Jeff Buckley, 1997, drowning

Michael Hutchence of INXS, 1997, suicide

Aaliyah, 2001, plane crash

Layne Staley of Alice in Chains, 2002, drug overdose

Lisa “Left Eye” Lopes of TLC, 2002, car accident

Jam Master Jay of Run-D.M.C., 2002, murdered

Elliott Smith, 2003, suicide

Dimebag Darrell of Pantera, 2004, murdered

Ol’ Dirty Bastard, 2004, drug overdose

J Dilla, 2006, lupus

Jay Reatard, 2010, cocaine toxicity

Amy Winehouse, 2011, alcohol poisoning

Scott Weiland, 2015, drug overdose

Now consider the list of people who haven’t died. With the exception of the Beatles, all the artists who put out the bestselling albums of the aughts are still alive: ’NSync, Norah Jones, Eminem, Usher, Linkin Park, Creed, Britney Spears, and Nelly. The same goes for the makers of the bestselling songs: Flo Rida, Lady Gaga, Jason Mraz, Timbaland and OneRepublic, the Black Eyed Peas, Soulja Boy, Coldplay, Taylor Swift, and Katy Perry. None of the major rappers of the modern era—Jay Z, Outkast, Master P, DMX, 50 Cent, Ludacris, Lil Jon, T.I., Kanye West, Lil Wayne, Drake, Kendrick Lamar—have died. All the most popular rock bands—including Radiohead, Green Day, the Foo Fighters, the White Stripes, Muse, Arcade Fire, the Black Keys, Vampire Weekend—have remained intact. Country superstars such as Kenny Chesney, Brad Paisley, Tim McGraw, and Eric Church might sing about drinking whiskey, but none ended up like Hank Williams.

There are four possible explanations for this.

(1) Pop Stars Are Healthier Now

Out of the thirteen deaths listed above, roughly 38 percent are drug-related. If you attribute suicide to untreated mental illness, that still means just under 50 percent of the list is made up of accidental demises. It seems generally true that pop stars these days are aware of the risks of abusing hard chemicals and will find a way to stop doing it before they are killed. The most obvious example is Ryan Adams. Throughout the aughts, Adams (along with that bozo from the Libertines) was among the most demonstrative consumers of drugs in popular music. Adams occasionally referenced his drug use in his songs, but more often he just appeared to be totally hammered. In another time, he might very well have died. Instead Adams moved to Los Angeles, started hiking, and married Mandy Moore (whom he later divorced in 2015). He’ll probably live to be 112 and release 1,012 albums.

(2) Pop Stars Are Luckier Now

Freakish, flat-out fucked-up pop-star deaths occur with less frequency now. R & B singer Johnny Ace mistakenly shot himself in the head with a gun he thought was unloaded in 1954. Chicago guitarist Terry Kath accidentally unloaded a bullet into his skull in 1978. Yardbirds singer Keith Relf was electrocuted by his own guitar in 1976. Acrobatic soul star Jackie Wilson had a heart attack onstage in 1975, went into a coma that lasted nine years, then died in 1984.

Now, Jeff Buckley, Aaliyah, Jam Master Jay, and Dimebag Darrell weren’t very lucky. Buckley drowned in a Memphis river. Aaliyah’s plane crashed while en route from a music-video shoot. Jam Master Jay was murdered in a recording studio. Dimebag Darrell was unfortunate to have a deranged fan who blamed him for the breakup of Pantera and retaliated by gunning him down while he was onstage in Ohio with his new band, Damageplan. But generally, rubbing a pop star for good luck is a solid policy.

(3) Pop Stars Are Under More Scrutiny Now, Which Makes Dying More Difficult

In 2011, Caleb Followill of the semishitty and periodically enjoyable rock band Kings of Leon appeared onstage in Dallas in a visibly intoxicated state. Near the end of the show he said the following: “I’m gonna go backstage, and I’m gonna vomit. [Then] I’m gonna drink a beer, and I’m gonna come out and play three more songs.” Then he proceeded to not come out, presumably because he got lost somewhere between “I’m gonna vomit” and “I’m gonna play three more songs.” Some version of this scenario has played out approximately 1.6 million times in rock-show history. And yet because Followill was caught on video and the incident was subsequently run through the Internet news cycle, tour dates were canceled, and Kings of Leon went on a short hiatus.

Kings of Leon is a cheesy rock band, and the members were caught on tape acting like buffoons. But this incident also illustrates how little patience the public has now for displays of decadence. Being too drunk to perform used to be considered the ultimate in rock-star cool; the mythology of the Replacements is based almost entirely on this idea. But now it’s perceived to be pathetic—which it is, but it always was: it just wasn’t always thought of that way.

Decadence is only acceptable in hip-hop, though even rappers are no longer allowed to enjoy the drug-taking, groupie-banging lifestyle. On the cover of Drake’s 2011 LP, Take Care, the Toronto rapper sits at a table in a gold-colored room covered in expensive-looking art. The table is ornamented with an elegant candleholder, and Drake is holding a motherfucking goblet. And Drake looks miserable, because motherfucking goblets now signify a depressing lifestyle.

(4) Pop Stars Have Subliminally Absorbed the Lessons of Biggie vs. Tupac, Which Has Made Them Safer

Let’s circle back to Justin Bieber. He has long claimed to be a Tupac fan. When Bieber appeared on the radio station Hot 97 in 2012, he said he could “spit” Tupac verses at age eight. (Bieber’s father, Jeremy, was a fan.) During a trip to South America in 2013 for his Believe tour, Bieber Instagrammed graffiti tags he spray-painted on buildings in Bogotá, one of which was “RIP Tupac.” As Bieber has gotten older, he has dressed more and more like Tupac, appropriating various Pac-like bandannas and tattoos.

What Bieber hasn’t done is participate in a rapidly escalating conflict with another superstar surrounded by a scary entourage. He hasn’t courted a violent lifestyle in a serious or authentic manner. He has not introduced Suge Knight into his inner circle. He has dabbled in Tupac’s iconography, but he hasn’t come close to approaching the void that swallowed Tupac whole. By the time Bieber was memorizing Tupac lyrics, Tupac had already been dead for five years. Tupac has always been a dead person as far as Bieber is concerned. He grew up in a world where a white Canadian could pretend to be Tupac without suffering the consequences of doing so.

Arguing that Tupac’s death indirectly spared Justin Bieber’s life is vaguely obscene, I know. I just want so badly for Biggie vs. Tupac to mean something. Overanalyzing pop rivalries is enjoyable escapism, because most of them are harmless. But thinking about Biggie vs. Tupac gives me no pleasure. I want to believe that Biggie vs. Tupac made subsequent generations smarter, but even if it did, that doesn’t change how pointless it was. I am pushing to find meaning when in fact there can be no meaning at all. Two young men died for no good reason, and their murderers will likely never be brought to justice. There’s nothing deep about it. It’s as empty as empty can be.