While Love and Hip Hop is currently a hit reality show, the pairing of those two terms is far from new. Whether we admit it or not, Hip Hop has always loved a gossip story just as much as it’s loved a good old fashioned romance. Rappers canoodling with rappers, actors, models, and other celebs, has always provided decent fodder when the music wasn’t at the forefront. Of course the break-ups prove to be just as interesting as the make-ups sometimes. Over the last 25-plus years, as Hip Hop ascended to global mainstream success, the private lives of its stars have also become public interest. That makes the “behind the scenes” info all the more interesting, learning about the reasons behind certain songs, interviews, and appearances in music videos. As Cupid shoots his arrow over this week, HipHopDX collected some of the most memorable couples. Some of these love affairs ended amicably, while the pain of others still echoes on. Regardless of the result, Hip Hop enjoys a good love story, even if its about the absence of it.

Diddy & Jennifer Lopez (circa 1999-2001)

J-Lo made a dazzling appearance in Diddy’s (then “Puff Daddy”) 1997 video for “Been Around The World.” In the months to come, the two began to appear as a power-couple in Hip Hop that rivaled Jay-Z and Beyonce 10 years later. However, the 1999 New York City club shooting not only sent Shyne away, it cast away Cupid. Reportedly traumatized by lifestyle of “makin’ moves with Puff,” J-Lo left the Bad Boy Records mogul in early 2001 for a notorious string of botched relationships.

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