Hip-Hop’s 10 Most Painful Breakups: A Valentine’s Day List

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Valentine’s Day is almost here, and while much of the attention paid to the festivities focuses on the positive side of romance (or its commercial manifestations, at least), no celebration of love can be entirely separated from our knowledge of what happens when it ends: The Breakup.

In hip-hop, there’s still plenty of attention paid to who is dating whom, who cheated on whom with who, and the more specific but no less popular topic, “ladies that Kanye has sexed.” But for our money, the most interesting relationships are the creative ones, and when they implode, it is often spectacular, resulting in more art and more entertainment. That being said, when shit gets too real, it can end in tragedy more permanent than any romantic heartbreak.

When rappers break up, they’re going to let you know about it, so there’s no shortage of material. So for Valentine’s Day this year, here’s a look back at ten of the most memorable hip-hop breakups; partnerships that generated great art, controversy, gossip, and heartache.

Gucci Mane and Young Jeezy

This friendship was probably doomed from the start. When the pair recorded the hit single “Icy,” Young Jeezy assumed that the collaboration would appear on his debut album, Let’s Get It: Thug Motivation 101. Instead, it appeared on Gucci Mane’s 2005 LP Trap House, helping drive Mane’s ascendance and infuriating Jeezy, who claims he was never even paid for his appearance. Jeezy then put a $10k bounty on Gucci’s chain, and Gucci was charged (and acquitted) with the murder of a Jeezy associate. The feud stretched on for years, with many diss songs, brawls, even a (broken) truce thrown in for good measure.

Jim Jones and Max B

This beef has cooled recently, mostly because Max B is serving what is effectively a life sentence in a New Jersey prison. But back when Diplomats associate Jim Jones was starting his new label/crew ByrdGang, Max B was a rising producer/rapper in the crew. They were successful, playing shows and selling records with the momentum from Cam’ron’s Diplomats success, but it didn’t take long for money to come between them. Max B, salty that he was writing hits for the crew but only taking home $300 from shows with $15,000 guarantees, decided it was time to cut ties. In a jailhouse interview with Complex, he said: “Once I knew I had the buzz, I went in the studio, stole a few more records, my records, and I started something I knew the city, the Rap game, was gonna eat up. I started a beef. I had to. It was me against the world.”

Andre 3000 and Big Boi

More of a separation than a breakup, one of hip-hop’s greatest duos hasn’t made an album together since 2000’s Stankonia, the odd stay-together-for-the-kids double LP Speakerboxxx/The Love Below notwithstanding. It’s clear that they can still make magic, as the above track, a cast-off from the sessions for Big Boi’s debut solo album, proves. But that track was never officially released due to “contractual obligations,” and they couldn’t even make it through their reunion tour without squabbling. We’re not sure what it will take to reunite one of hip-hop’s most powerful artistic marriages, but we’re hoping for a reconciliation.

The Notorious B.I.G. and 2Pac

One of the more tragic breakups on this list, Biggie and Pac’s feud was better known than the budding friendship that was left in its wake. Despite working on opposite coasts, Pac had New York ties, and the two respected each other’s talents. But after he was shot in the elevator at a New York recording studio in which Biggie and his entourage were also present, Pac never forgave his rival, convinced that he was somehow responsible. The subsequent war on wax, its rabid media exploitation, and the tragic conclusion changed the way rappers beef forever.

Meek Mill and Drake

If you want evidence of the most obvious legacy of the Biggie/2Pac beef in contemporary hip-hop, look no further than the beef that launched a thousand memes. Beefs generate attention, which drives sales, so they’re never going away; but no one wants to die, either, so now they’re much tamer and involve a lot more GIFs. All you really need to know is that these two broke up over a tweet: Meek was incensed that Drake didn’t tweet out a link to their collaboration “R.I.C.O.,” the third single on his second album, Dreams Worth More Than Money. The rest is well documented; Meek accuses Drake of using ghostwriters, Drake claps back with some diss tracks, Meek keeps tweeting, etc etc. At the end of the day, Meek’s claims were backed up by evidence, but no one cared. A rap beef settled by a Klout score.

Eric B. and Rakim

These two seemed unstoppable in the late ’80s; the God MC with one of the illest producers in the game. They made classic after classic from ’87-’92, but when their MCA contract expired, and Eric B. refused to sign the new deal, things got sticky. Each wanted to go solo, but secretly worried about his future without the other. The legal wrangling around the contract dispute got so ugly that the partnership dissolved, with Eric B. independently releasing a solo album, and Rakim putting out The 18th Letter on Universal. Rakim has had a middling career since, and we have no idea where Eric B. is these days.

Jay Z and Damon Dash

One of hip-hop’s most famous couples, the tag team dominated mainstream hip-hop in the late ’90s, as their record label Roc-A-Fella leveraged Jay Z’s chart successes into a small music empire. While Jay Z’s ascendance has been steady, Dame’s story has been more of a roller-coaster ride. Most of the true story of what exactly drove the acrimony between the two is not public, but Dash is a legendary asshole, and it’s likely his demeanor didn’t fly as smoothly in corporate settings as Jay Z’s. With the Roc going more and more corporate by the day, the relationship was doomed. When Island Def Jam bought out the controlling stake in Roc-A-Fella, the two split for good, and haven’t been on good terms since. At least we’ll always have that double-fist champagne dance, Dame.

Lil Wayne and Baby

The story of Lil Wayne and Bryan “Baby” Williams is way too thick to properly dig into here, but here’s the CliffsNotes version: Baby (also known as Birdman) took in Wayne, whose biological father was absent, as a youngster. He introduced him to the rap lifestyle at an early age, with Wayne admitting that his first sexual experience was at 11 years old, when he was raped in front of a kitchen full of people by a female associate of Baby’s. It was all smiles for years, though, with the Cash Money conglomerate Baby built serving as a launching pad for Wayne’s mainstream career, which then gave way to Wayne’s Young Money imprint, which in turn helped launch the careers of Drake and Nicki Minaj. Things devolved into a messy lawsuit, with Wayne claiming Young Money was stiffed for stacks of cash. It appears they’ve kissed and made up — “This my motherfucking son and Ima die for him,” Baby was recorded saying on stage — so hopefully they’ve squashed the beef for good.

Ice Cube and NWA

Ice Cube was always unquestionably the star MC of NWA. Eazy-E may have been the frontman, the group’s de facto leader, but it was Cube who was writing rhymes for his fellow members, and Cube who had the most to gain by going solo. In hindsight, it was inevitable, but in 1990, Eazy was still running the group like a gang, and he was definitely not cool with Cube leaving the gang due to royalty disputes with the group and its manager, Jerry Heller. Naturally, Cube struck with his greatest weapon, his raps, releasing the scathing diss track “No Vaseline,” a curious breakup record that suggests forcible anal sex as punishment. Cube’s solo career would prove quite successful, and Dre would leave shortly afterwards to pursue his own endeavors, free of Eazy and Heller.

Dr. Dre and Eazy-E

While Cube’s diss track was so foul it had no chance of mainstream success, Dre was a bit smarter with his middle-finger salute to his former bosses at NWA, Eazy-E and Jerry Heller. He didn’t even give them the respect of an entire track, making room on “Fuck Wit Dre Day (And Everybody’s Celebratin’)” for harsh words on Tim Dog and Luther Campbell as well. The second single from his debut solo album The Chronic, it would help cement Dre’s place in the hip-hop canon, while publicly declaring his separation from Eazy-E. After Eazy died a couple years later from AIDS complications, Dre softened up a bit, and has since expressed regret for the way their relationship ended, paying tribute on screen, on stage, and on wax.