Lamont's Lists: The Top 50 Hip Hop Songs Of All Time (50-41)

"50 years down the line you can start this...'cause we'll be the old school artists. And even at that time, I'll say a rhyme, a brand new style...ruthless and wild." - KRS-One.

I think it's cool that KRS-One, Boogie Down Productions' indomitable frontman, had the foresight to write that line way back in 1988 for his song I'm Still #1. During a year that is still considered by many (myself included) to be hip hop's single greatest ever in terms of creative excellence, KRS asked everybody to just chill and enjoy the beautiful music. His message being: it's too soon for generational divides between old school and new. And now is not the time to get into premature squabbles about the best rappers, rap albums and rap songs. He was confident that he would still be around making hit records well into the future, so suggested we wait a few decades for history to play out before engaging in such discussions.

Well here we are. It's 2023 and we are now celebrating hip hop's 50 year anniversary. In honor of such a tremendous milestone I have finally gotten around to compiling the definitive list of my 50 all-time greatest rap songs. To say that this was a challenging exercise would be an understatement. After weeks of culling through my own library of tracks, studying old charts and reflecting on the favorites that I've repeatedly come back to over the years, I came up with about 200 songs that I thought were worthy of consideration. From there I applied a few rules and then slowly, painfully (there were many that were super hard to leave out) narrowed the list down to my Top 50.

The rules I applied were pretty straight-forward. For me, this particular list is about the quality of the song (the vocals, production, originality and wow factor). I did not give special consideration to songs based on their sales volume, popularity or even their overall influence on the genre (that's another list as posted HERE). Simply put, if the track did not age well, it did not make the cut, no matter its nostalgic value or historical significance. The only other rule I applied was an attempt to remove recency bias. Therefore, there are no songs included that have been released within the last 5 years. 

Obviously, ranking the top 50 songs (in order no less) out of millions that have been recorded over the past 50 years is highly subjective and riddled with personal preference. Nonetheless I took my best shot at an impossible task. The point here is not to dwell on the actual numbers (although, as always, I welcome healthy debate), but to think of this as a love letter to hip hop. All of these songs are fantastic, and I am fully aware that there are thousands more incredible recordings that I failed to include.

Take a read (and a listen by clicking on the song title) of my write ups below. And please let me know your thoughts and opinions. I love the feedback. 

By the way, I am happy to report that I just saw KRS-One live in concert a few weeks ago. If he was not "still #1" as he predicted, the man was certainly damn close. Happy Anniversary Hip Hop. Cheers to the next 50!

Lamont

Apple Music Playlist

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50. Passin' Me By - The Pharcyde (1993) - During the height of Dre, Cube and NWA's gangsta rap reign, an alt collective from South Central LA emerged with a quirky tune about the perils of shooting your shot at your high school crush. Quite a testament to the incredible diversity of styles and influences in hip hop.

49. Check The Rhyme - A Tribe Called Quest (1991) - On Check The Rhyme, the lead single from the A Tribe Called Quest's exalted 2nd album "The Low End Theory", Phife and Q-Tip passed the mic back and forth with joyous aplomb. The song's breezy, infectious bounce sounded like it was improvised on the spot while hanging out on the stoop back home in Queens.

48. Still Dre - Dr. Dre (1999) - By 1999, many of us had assumed that after a hell of a run, Dre's best days were behind him. Boy did that opening piano loop put us on notice that we were dead wrong.

47. Alright - Kendrick Lamar (2015) - "If God got us...then we gon' be alright". During an era of trauma and unrest, Kendrick elevated his stature by delivering a protest anthem of biblical proportions - providing a moment of reassurance that Black America desperately needed.

46. Ms. Fat Booty - Mos Def (1999) - The playful rhymes, the clever couplets, the charismatic flow, the Aretha Franklin sample, the fits and starts of a budding romance...it's all there. And like the woman in the song who is the object of Mos Def's affection...Ms. Fat Booty is a thing of beauty.

45. Children's Story - Slick Rick (1988) - I don't think there has ever been a hip hop song that features more captivating end-to-end storytelling - perfectly paced, wily, original, refreshingly easy to follow and generally all-around pleasing to the ear. Children's Story, Slick Rick's endearing parable about a little boy who was misled, reigns supreme above all others. Knock 'em out the box Rick.

44. Stakes Is High - De La Soul (1996) - An underrated aspect of De La Soul's greatness is how they have always taken on the responsibility of playing the role of Hip Hop's conscious. In 1996, on Stakes Is High, they reminded us of just how far the music had drifted from its roots and that as a culture we had a lot to lose if we didn't stay true to what made this music great in the first place.

43. The Symphony - Marley Marl (1988) - With a tongue-twisting, metaphor-laced lyrical outburst that defied gravity, many still argue that G Rap stole the show on The Symphony, one of hip hop's greatest ever posse cuts. But, believe it or not, I still give a slight nod to the one and only Big Daddy Kane, who heard his counterpart's epic performance, cleared his throat and then calmly, confidently, rose to the occasion.

42. The Rain (Supa Dupa Fly) - Missy Elliott (1997) - On The Rain Timbaland gifted us with a stutter-stepping, herky-jerky masterpiece of a track that was somehow matched - in timing, weirdness and personality - by Missy's dynamic delivery.

41. So Wat Cha Sayin' - EPMD (1989) - By the time the '80s came to a close, the Strong Island duo EPMD had already established themselves as formidable hit-makers. So Wat Cha Sayin, the hard-charging lead single from their second album, would propel them to the status of "all-time heavy-hitters" by highlighting their uncanny ability to elevate straight-ahead battle rhymes and propulsive beats into something undeniably potent.

Check Back Later To See The Rest Of The Top 50 And Find Out Which Song Is #1