Updated: May 6, 2019
Written by Jeremy Schnapp
1) Black Thought - Web
Black Thought of The Legendary Roots Crew is without a doubt my favorite rapper of all time, but it's difficult to explain why in just one song. I don't think I've ever heard him spit a bad verse, and there aren't very many questionable lines either. In "Web", Black Thought goes off for 3 minutes straight on a difficult beat and absolutely kills it. Please do yourself a favor and listen to The Roots' massive back catalog. Pick any album, give it a spin, and you won't be disappointed.
2) MF DOOM - ALL CAPS
You won't find too many rappers that are really weird but still very enjoyable. MF DOOM is one of a kind, and the best-known track from arguably his greatest album (Madvillainy) shows why. The fact that he works so well over such an odd beat, the dense internal and multisyllable rhymes, and the monotone flow. This song is the epitome of DOOM.
3) Andre 3000 - A Life in the Day of Benjamin Andre
Andre 3000 is one of the best storytelling rappers there is. In a few minutes, he's able to tell us all about how he got started in music, his relationship with Erykah Badu, his son, and more. He's also got an unquestionable smooth voice and flow, and I think this song showcases that pretty well.
4) Nas - N.Y. State of Mind
The quintessential Nas track, and he recorded it when he was 19 years old. This is perhaps the most well-known track from Illmatic, regarded by many as the best hip-hop album of all time. If you give it a listen, I think it'll become obvious why that opinion is held by so many people. Nas is incredible at painting a really vivid image, and he does so on this track by telling us about the city and its darker underbelly. Although this isn't necessarily my favorite Nas song, it's loaded with multisyllable rhymes, great wordplay, and amazing storytelling, which is why I think it best showcases Nas's abilities.
5) Mos Def - Mathematics
Mos Def may not be the most consistent rapper in the game, but he's spit some of the best verses of all time - the first verse off Mathematics is a prime example. Mos Def (is he Yasiin Bey still?) absolutely kills it on this classic DJ Premier beat. A lot of conscious rappers come off as too preachy or have mediocre flow, but Mos Def sounds really genuine and doesn't sacrifice any of his abilities when trying to educate the listener.
Who's your favorite rapper of all time, and can one song explain to me why?