Date: 8/22/2007

Getting one rapper to commit to being in a particular place at a particular time can be challenging enough. But five superstar rappers all on stage at once? That's next level. The planets aligned back in 2007, when Jay-Z, 50 Cent, Diddy, T.I., and Kanye West all got on stage at Madison Square Garden when the Screamfest, headlined by T.I. and Ciara, came to New York. Tip had pulled out Kanye, who pulled out Jay, and 50 and Diddy who were both in the building sensed a moment and decided to cash in on it. 

For T.I., it was a priceless welcome to New York (it was his first headlining show there) from the biggest rappers in the city. For Kanye and 50, it was a welcome moment of congeniality in the run-up to their much-hyped album release date showdown (both dropped LPs on September 11 that year). For hip-hop, it was straight-up history.