The best old-school rappers and their greatest hip hop songs

When it comes to talking about old-school rappers, it’s necessary to define the valid dates to base the selection on. Once that’s done, choosing representative rap or hip-hop songs from each artist becomes a bit simpler. The challenging part, clearly, is setting the boundaries, as even in the 2000s, people were referring to old-school rap to describe the previous decade, and possibly something similar in the 90s. After all, since its emergence in the 70s, the genre’s evolution has been constant, reaching our days as a blend of mumble rap (disdained by lovers of past hip-hop) and artists who have preferred to elevate their favorite singers through their songs and their own personal style.

In this article, I’ve considered that old-school rap songs end in the year 1999, although it’s obvious that what existed until 2010 is already considered from a different era due to the evolution of the following decade. Considering that the blog is organized by old music and current music, which are further divided into songs before the year 2000 and after the year 1999, it seems to be an intrinsic logic of this page. If you add to that the fact that hip-hop itself often defines its songs in that way, it seems like a precise separation.

However, another clarification is necessary, since the blog will not only recommend American old-school hip-hop songs, but you will also find a selection of Spanish hip-hop music featuring some of the great old-school rappers. The need to specify different dates for discussing rap and songs in this latter case seems obvious, knowing that the period in which solo artists or serious collectives of this genre started appearing in Spain is much later.

Hip-Hop Songs by the Greatest Old-School Rappers

So, in this playlist (whose link you’ll find just before starting the list of rap songs and old-school rappers), the idea is to build it under the “keep it real” norm, even though sometimes doubt remains. Whether they’re from the East Coast or the West Coast, from the Bronx, Harlem, or Staten Island, the important thing is that we feel honesty in their words. If we recently recommended various romantic rap songs in another entry, here we’ll focus on the personalities they exhibited when writing, without forgetting the beats and production, which are always essential in shaping many of these artists.

That being said, let’s dive into the best hip-hop songs created by the most important old-school rappers (or at least the favorites of this blog). If, as you go along, you believe that a key name is missing, we invite you to let us know in the comments. As you’ll see below, some names became known in the late 90s, producing most of their work in the following decade. These rappers could be considered, according to our criteria, as part of the new school, but they deserve a mention precisely because they paved the way for a new wave of rap that largely coincided with the end of the wars and the deaths of some rap greats, such as 2Pac and Biggie. In fact, the turning point could be Dr. Dre’s 2001 album (released in 1999).

De La Soul – Me Myself And I

We start our selection of hip-hop songs with De La Soul. Because when we talk about old-school rappers, we’re going back to the 80s and early 90s, trying not to create another monograph about the same old names, the ones we’ve already talked about in other rap song playlists.

Here’s Me Myself And I, a song from 1989 belonging to the album 3 Feet High And Rising. Formed in 1987, the trio of rappers is still active, offering great new tracks that often surpass the number of listens of their commercial hits. It’s surprising, therefore, that they don’t have the same media impact as other famous names in the scene.

Grandmaster Flash – The Message

As we’ve told before, Grandmaster Flash is one of the pioneers of rap, using his mixing skills to find sounds that fit to create breaks. From there, the progression to being part of bands and the emergence of hits like The Message, a song released in 1983 as part of the album Grandmaster Flash & The Furious Five. In it, the group composed of DJ and rappers Melle Mel, Kidd Creole, Cowboy, Scorpio, and Rahiem mixed genres and styles such as electronic, hip-hop, funk, soul, and disco music.

Rakim – When I B On Tha Mic

If we talk about pioneers of hip-hop culture and essential names in old-school rap, Rakim is one that must be mentioned among the notable ones. Committed, innovative in his flow delivery, and above all, a true wordsmith whose lyrics harmonize melodies. Here’s an audio-visual example with When I B On Tha Mic.

EPMD – Da Joint

One of the things we were clear about when entering the topic of the best old-school hip-hop songs was undoubtedly not repeating names or songs that have already appeared in other posts and playlists. Therefore, so you can find other slightly more alternative songs, each representing the best of its era and origin, here’s EPMD. In 1988, they released their masterpiece Strictly Business, which marked the beginning of a discography where the word “business” always appeared in their titles.

Mobb Deep – Shook Ones, Pt. II

Although many might remember the song Shook Ones, Pt. II for appearing in the movie 8 Mile, aligning with the years when Eminem’s life seemed to be unfolding (or his alter ego’s life), the truth is that Mobb Deep is a true emblem of old-school rap. This song is one of the most significant hip-hop songs of its time, leaving its mark with its beat.

LL Cool J – Mama Said Knock You Out

The release of Mama Said Knock You Out in 1990 confirmed LL Cool J as an undeniable talent in rap. Like many others (Ice-T comes to mind, as well as Ice Cube), acting took them away from their musical career almost entirely, perhaps largely because one sometimes loses inspiration to write.

As an interesting fact, during these years we’re discussing, the purity that many sought in hip-hop, combined with LL Cool J’s ability to blend rap and pop, cost him the respect of many rap fans. They had to eat their words when the Queens rapper came with this track we’re listening to.