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

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.