Questlove's Top 50 Hip-Hop Songs of All Time

What makes a great hip-hop song? Ahmir "Questlove" Thompson chooses his favorites.

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Pete Rock and C.L. Smooth,
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39. Pete Rock and C.L. Smooth, "They Reminisce Over You (T.R.O.Y.)" (1992)

Hip-hop's fourth stage – '92-'97, a.k.a. the renaissance period – was a peak into the "boring" section of our parents' record collection. Of course, the obvious stuff (P-Funk/James Brown/Kool & the Gang) were the tools of the third stage – '87-'92's classic period – and used to great effect. If this period served the jocks well in Hip-hop High, then to make high art required a specific flexibility that the nerds excelled in. Soon artists like Monty Alexander, Vic Juris and Ahmad Jamal were allowed to play in the same reindeer games that their funk peers previously denied them access. The leaders of the New York renaissance were Gang Starr's DJ Premier, Tip and Ali from A Tribe Called Quest, the Large Professor of Main Source, Diamond D and Heavy D's cousin from Mount Vernon, Pete Rock. They made smooth jazz rugged by fusing it with crispy breakbeats. So lethal was this combination – especially with Tom Scott's rolling sax etched in your brain like a tattoo – I'm certain to this day that people forget that this was a song of mourning and reflection for a loved one. This song proved that hip-hop was as gorgeous as a painting in the Louvre.

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