10 Best Old School Rap Songs

For a sampling of the heart of the old school, look no further than the ten best old school rap songs. Covering a wide range of styles and topics, these hip hop hits can be playful, party-centric, or unapologetically raw. The best part? All these tunes hold up after several listens.

  1. “Freaks Come Out At Night” – Whodini. Unless you’ve followed hip hop from the early days, then chances are you haven’t heard of Whodini. They were one of the early popular rap groups whose beats and lyrics pushed hip hop to another level. Listen to it for a taste of old school rap songs at their best.
  2. “It Takes Two” – Rob Base & DJ EZ Rock. What started as an old school rap song enjoyed mostly by hip hop heads has turned into one of the most popular and well-spun rap tunes of all time. Sure, it may be accepted by the mainstream now, but back then, it was straight hip hop. It also features everything that made rap what it is today: a strong beat, memorable verses, quality turntablism and samples galore.
  3. “Bad” – LL Cool J. A young, cocky punk named LL Cool J arrived on the scene in the late 1980s with a brash style and a new sound. “Bad” was his first hit single that managed to capture the rugged and raw essence of old school rap songs.
  4. “Raw” – Big Daddy Kane. In his day, Kane was considered one of the most lyrically complex rappers on the scene. With his fast flows and tight rhymes, Kane quickly ascended the ranks of hip hop royalty, and “Raw” stands today as his ultimate triumph. Even all these years later, it is an old school rap song with a vibe and feel similar to many contemporary underground tunes.
  5. “The Humpty Dance” – Digital Underground. Unless you've lived under a rock for the last 20 years, then you've heard Digital Underground's signature tune. Much like "It Takes Two," "Humpty Dance" stays aloft by the power of its popular appeal. That doesn't mean it's not a fun song, however, as well as one of the best old school rap songs that you can listen to over and over again.
  6. “Children’s Story” – Slick Rick. Slick Rick was an icon of the old school hip hop era. He possessed one of the most enviable flows in the industry, and his storytelling abilities were on par with the best. "Children's Story" shows off these abilities better than any song in his collection and remains one of the best old school rap songs.
  7. “Me Myself & I” – De La Soul. When De La Soul released "Three Feet High & Rising” in the late 1980s, it marked a shift in how hip hop would be perceived. The biggest smash from that album was undoubtedly “Me Myself & I.” With a laid-back beat and unforgettable chorus, De La Soul gifted the world with one of the best rap songs of both the old and new school.
  8. “Don’t Sweat the Technique” – Eric B. & Rakim. Eric B. & Rakim had many hits during their heyday of the late 80s and early 90s. And while it's arguable which of their songs should be included on this list, “Don't Sweat the Technique” has perhaps the strongest staying power of them all.
  9. “Fight the Power” – Public Enemy. As a group, it didn't get any bigger in the old school than Public Enemy. They define what hip hop was all about in the early days: activism, rebellion and fighting injustice. No song better encapsulates those themes than “Fight the Power.” Listen to it today for a feel of how in-your-face hip hop used to be.
  10. “Scenario” – A Tribe Called Quest. This song didn't get quite the love that songs like "It Takes Two" and "Humpty Dance" received from mainstream or casual rap fans. There is no denying, however, it is a true hip hop classic that sounds as if it could have been released today, never mind eighteen years ago. With a bevy of star cameos, a thumping beat and a can't-get-it-out-of-your-head chorus, "Scenario" stands as the best of the old school rap songs.

 

 

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