5. “They Reminisce Over You (T.R.O.Y.)” (1992)

Pete Rock & C.L. Smooth

The Mount Vernon, New York duo composed of producer Pete Rock and rapper CL Smooth only hit #58 on the charts with “They Reminisce Over You (T.R.O.Y.),” but its impact has proven to be lasting. It serves ostensibly as a tribute to Heavy D & The Boyz’ Trouble T. Roy — who died in 1990 after falling off of an exit ramp. But CL uses the track to tell his own story, and in the end it’s an unfiltered testament to family, perseverance, and generational contrasts. The song is hip-hop’s idyllic balance of sophistication, substance and style. -Jake Paine

4. “Juicy” (1994)

Notorious B.I.G. 

Only 21 at the time, cockeyed Brooklyn dope dealer Biggie Smalls made a song for the ages. “Juicy” is a rags-to-riches anthem that describes his rapid ascension from slanger to rap star, mixing hard urban truths with the joys of excess, Biggie was at the forefront of a group of MCs who ushered in the second wave of East Coast rap, combining bombastic swagger with a perfection of craft. “Juicy”‘s secret sauce? The sense of absolute joy he brings to the tale. -Daniel Kohn

3. “The Message” (1982)

Grandmaster Flash and the Furious 5

The first song that truly showcased what rap was capable of, “The Message” came only four years into recorded rap history. But unlike the songs that came before it, Grandmaster Flash and The Furious Five’s magnum opus wasn’t just interested in rocking the party and shouting out zodiac signs. Instead, “The Message” reflected the struggle that rap itself emerged from. Arguably the most important song in the genre’s history, it changed hip-hop’s format; instead of attempting to re-create the party atmosphere on wax, it shifted the focus to structured songwriting. -Chaz Kangas

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