50 Greatest Rap Songs of All Time (& Why)

This is my ranked list of 50 greatest rap songs of all time. My own works are excluded to avoid the situation where a single artist dominates the whole chart, which can defy the purpose of making such a chart. By the way, what exactly is my purpose of coming up with this list? To reminisce about the good old days? Nay. I may just want to put it out there to see if there are other people who happen to be on the same page. At least, those who are not will be kindly notified. 

We shall begin from the bottom of the list.

50. “Why?” by Jadakiss, Anthony Hamilton

Solid beat and excellent rap skills. This song sets the minimum standard that a song must meet in order to make the list.

49. “B-Boy Stance” by Cassidy

Pretty much the same reason.

48. “Get No Better” by Cassidy, Mashonda

Nice composition, lovely melodies, and solid rap.

47. “Super Freak” by Shawnna

Dope beat, sexy bass, and excellent vocal performance.

46. “Tight” by Remy Ma, Fat Joe

Top-notch production and rap skills. The intensity of emotional expression is impressive.

45. “My Lifestyle” by Fat Joe

Iconic beat and powerful rap that bridge Old-school and New-school Hip Hop. 

44. “Envy” by Fat Joe

A sincere and heartwarming masterpiece.

43. “Represent” by Nas

Unparalleled rap skills. 

42. “Memory Lane (Sittin' In Da Park)” by Nas

Old-school Hip Hop at its finest.

41. “N.Y. State of Mind” by Nas

An iconic masterpiece uncompromisingly conveying the essence of Hip Hop.

40. “I Need Love” by LL Cool J

Very unique story-telling demonstrating that there is much more to Hip Hop than glorification of violence.

39. “Hey Lover” by LL Cool J, Boyz II Men

A timeless masterpiece at the intersection of alluring melodies, exceptional rap skills, and sincere story-telling. 

38. “My President” by Young Jeezy, Nas

An expressive and uplifting New-school Hip Hop masterpiece.

37. “Everything I Am” by Kanye West, DJ Premier

Arguably Kanye West’s best work ever. One of the rare occasions where he is sober and sincere.

36. “Overnight Celebrity” by Twista, Kanye West

Twista’s unique rap style is not only characterized by its speed, but also its clarity, elegance, and emotional impacts on the listener. This song as a whole is very creative and well-thought-out.

35. “Hope” by Twista, Faith Evans

In this exquisite masterpiece, Twista raps a bit less fast. Meanwhile, the pleasant melodic qualities of his rap become even more prominent. The sincere self-expression, heartwarming story-telling, as well as the complexity of rhymes and rhythms distinguish this song as an enduring classic.

34. “Turn It Up” by Chamillionaire, Lil’ Flip

This song represents what New-school Hip Hop is all about: amazingly solid beat, chantable melodies, majestic vocal performance, and immensely stimulating musicality.

33. “Just a Lil Bit” by 50 Cent

A low-key New-school Hip Hop classic. Scott Storch, the producer of both this song and “Turn It Up”, has almost single-handedly defined the aesthetics of New-school Hip Hop. All elements in this song are minimalistic yet undeniably engaging. Its deceptively plain style is calm, amusing, and almost poetic.

32. “When It Rains It Pours” by 50 Cent

Elegant masterpieces like this came out one after another during the first decade of the new century, expanding the aesthetics of Hip Hop and separating it further and further from its primitive past. In short, in songs like this, rap itself is no longer the sole focus, but one of many interconnected aspects that come together to produce thoughtful depths and maximum emotional impacts on the listener. As a teenager, I used to enjoy listening to these songs all day long without even knowing the meanings of the lyrics.

31. “Poppin' Them Thangs” by G-Unit

Gangsta rap at its finest. One of the wonders of Hip Hop is how gang rappers were able to turn glorification of violence into a form of art, often with effortless grace and charm. Calm yet aggressive, this masterpiece is one of the finest embodiments of the spirit of gangsta rap.

30. “You Don't Know” by 50 Cent, Eminem, Cashis, Lloyd Banks

One of the toughest rap songs ever created. The incredibly firm and heavy beat gives the song a serious and aggressive undertone. The earth-shattering power of this work is not achieved with outright anger, but calm elegance and self-assurance.

29. “What's the Difference” by Dr. Dre, Eminem, Xzibit

Dr. Dre is perhaps the only producer whose successes have spanned both Old-school and New-school Hip Hop. Indeed, he was not only one of the founding fathers of the Old-school era, but also a defining figure in the new era. The amusing aesthetics and musicality of Dr. Dre’s production almost never disappoint. This song also includes one of Eminem’s earliest appearances in the rap scene. The rise and fall of this legendary rapper were going to become the central storyline of Hip Hop’s last golden age.

28. “Nuthin' But a G Thang” by Dr. Dre, Snoop Dogg

One of the few Old-school Hip Hop classics that have been able to stand the test of time and remain fresh and inspiring to this day. What gives this song a much longer lifespan than the vast majority of other rap songs of the 80s and 90s is the fact that it was not a typical product of the era strictly confined by the popular aesthetics at the time. While most Old-school rap songs are depressingly dull or annoyingly frivolous, something graceful, thoughtful and timeless about this song strikes a chord with music lovers at large.

27. “Compton” by The Game, will.i.am

The Game is an overachieving yet much underrated genius that has transformed the essence of Hip Hop. Arguably the greatest gangsta rapper ever, The Game is a captivating personality with a rare gift in rap. His natural voice is full of raw energy and youthful vitality, while he as a person is particularly intelligent and charismatic. At the time of releasing his first studio album in 2005, he had only had three years of experience in rap. However, he achieved full artistic maturity almost instantaneously. This song is from his second studio album released in 2006. While no individual elements of the song seem to be uniquely impressive, the work as a whole is simply breathtaking.

26. “Too Much” by The Game, Nate Dogg

One of the top-notch products of the creative chemistry between The Game and Scott Storch. The smooth and steady variations of the beat are the source of inspiration for The Game’s three unparalleled rap verses.

25. “Start from Scratch” by The Game, Marsha of Floetry

A profoundly moving yet largely forgotten masterpiece embodying the purest beauty of Hip Hop. Every line of the rap is bursting with heartfelt emotions. Dr. Dre’s production provides the rapper with a flexible framework and a contemplative undertone for him to unleash the maximum power of his intense self-expression. 

24. “We Ain't” by The Game, Eminem

Although the enormous amount of syncopation is the element of the song that stands out the most, the aesthetics and execution of the work as a whole are what make it timeless.

23. “One Night” by The Game

Perhaps the only rap song that I can describe with the word “poetic” without diminishing its meaning. A perfect mixture of profound emotional expression, flawless skills, and intellectual depths. Indeed, this song is so unique that there is simply nothing else similar in style.

22. “Let's Ride” by The Game

Another epic collaboration between The Game and Scott Storch. Just dope in every respect.

21. “How We Do” by The Game, 50 Cent

Gangsta rap at its finest (again).

20. “Dreams” by The Game

One of the hits from his first studio album which has remained his most sincere and moving masterpiece. The young rapper simply had so much to get out of his chest, and he was finally granted an opportunity and a platform after many years of struggles on the streets. As a teenager, I used to think the vocal performance of this song was less than perfect, and attempted to improve it by recording my own version. Today, I can see that everything about this song is just right. The Game’s voice seems to be slightly weaker than his other songs. That “weakness” is actually vulnerability, which is an indicator of strength.

19. “Put You On the Game” by The Game

What can I say about this one? Help me, please.

18. “The Way I Am” by Eminem

The next 8 spots on this list will be solely occupied by Eminem, one of the greatest geniuses in the history of Hip Hop. He is revolutionary not only for the fact that he is white, but that he was truly unique as a person and as an artist, and that he was never reluctant to be radically different. I used “was” on purpose, because, sadly, a few years later, anything unique about this man and his art was suddenly all gone. “The Way I Am” is one of his earliest masterpieces. Noticed he is showing off syncopation techniques throughout the song? Noticed how effortlessly he is able to achieve it? Noticed how much he had matured since “What's the Difference”? Well, you are witnessing the coming of a new era.

17. “'Till I Collapse” by Eminem, Nate Dogg

Two years after The Marshall Mathers LP, he released The Eminem Show which went on to influence a whole generation of rappers and producers, defining the most innovative and productive era of Hip Hop. I was one of the teenagers inspired by his music to pick up the mic and start learning to rap. To a 14-year-old, the empowering message and the ruthlessly rebellious spirit in his music are simply irresistible. In a sense, if you are numb to Eminem’s early works, your soul is old.

16. “Without Me” by Eminem

The most controversial part of Eminem and his music is his blatant vulgarity. Unsurprisingly, the provocative nature of some of his songs was also the main reason why he could achieve massive commercial success around the world. From the perspective of a critic, the vulgarity of his music actually does not feel “dirty” at all. In fact, the way he created his unique and deceptively frivolous style was pure genius. Throughout musical history, there has rarely been any composers or musicians who were able to invent something so radically different from anything in existence. Also noteworthy is the fact that he was not making an effort to be different. He was different.

15. “The Real Slim Shady” by Eminem

The older sister of “Without Me”.

14. “When I'm Gone” by Eminem

The fact that there are so many strikingly different facets of his personality and his music is the ultimate source of his endless creativity. In this song, there are not any slightest traces of the vulgarity and frivolity that define many of his other works. He has suddenly become tender, loving, and earnest. This is not a symptom of a split personality, but a clear sign of genius. Indeed, this song is a profound masterpiece that has redefined what Hip Hop is about by transforming its storytelling, compositional skills, and emotional substance through and through.

13. “Mockingbird” by Eminem

This song and “When I'm Gone” revealed just what level of artistry Eminem could potentially achieve. He was one of a handful of truly exceptional rappers who, at some point in their careers, had a shot at transcending the genre of Hip Hop and becoming self-conscious artists of far-reaching significance. However, just as he says during the intro of “Lose Yourself”: “Look. If you had one shot, one opportunity, to seize everything you’ve ever wanted, one moment, would you capture it, or let it slip?” Apparently, the path toward becoming a truly great and significant artist was not his choice. After he started to slip away from his integrity and unique creativity, that rare opportunity, which was truly a historic moment in hindsight, was gone forever.

12. “Stan” by Eminem, Dido

This stunning masterpiece is one of a handful of rap songs that are so great that they cannot be simply categorized as “Hip Hop” or “rap”. This song does not belong to the tradition of rap music. It seems to have come out of nowhere, or born out of a flash of inspiration. It is an absolute outlier in every possible way, and yet another piece of evidence that Eminem’s creative potentials could extend far beyond the boundaries of Hip Hop. What has stopped him from focusing on his art and discovering his own infinite potential? No one knows except himself.

11. “Lose Yourself” by Eminem

The culmination of Eminem’s creative power. The self-image that he projects in this song is one of immense confidence and courage. Ironically, in reality, after achieving unimaginable fame and success, he started to fall into an abyss of self-destruction and deterioration. From 2005 on, he has not created anything that can remotely compare with these 8 masterpieces on this list. To be precise, everything that he has created ever since has been total garbage. Eminem has disappeared into thin air, just like the sudden burst of extraordinary creative energy during his early days. What is still left in him today? Nothing but an utter void.

10. “Keep Ya Head Up” by Tupac

All of the 10 remaining spots at the top of my list are reserved for Tupac, the greatest rapper of all time except myself. To a large degree, Tupac is the only rapper who has transcended the tradition of Hip Hop and touched upon the deeper essence of music and art. In short, he has always had a message to convey, which separates him one hundred miles apart from a shallow-minded entertainer. Mu Xin once said: “Artists are like bits and pieces of Jesus Christ scattered everywhere.” Tupac was no less than an angel sent from another world. Growing up poor on the streets did not defeat his spirit or fill his heart with pessimism. Instead, poverty made him wholeheartedly committed to doing whatever he could to change the world for the better. His heart was pure and strong, which compelled himself to express himself through music.

9. “Me Against the World” by Tupac, The Outlawz

In many ways similar to Eminem’s rise and fall, after a few years of unbelievable productivity, Tupac sank more and more deeply into despair, self-destruction, and utter insanity, before his untimely death at the age of 25. Perhaps it was art itself that had thrown him out of balance. Perhaps he was already too deeply entangled with the dark side of street life. Perhaps an inescapable curse has been cast upon Hip Hop to prevent any rapper from attempting to achieve the highest level of artistry. One phenomenon is universal: no matter how powerful or successful an individual is, it is very difficult for him to overcome his own weaknesses and shortcomings. In Greek mythology, even gods are powerless when confronted with fate. One’s personality is one’s fate. While Tupac was a person full of empathy, intelligence and courage, he also had a short temper and an appetite for violence. Unfortunately, as the tension between him and the world around him escalated, the destructive energy within him was also amplified. The Devil finally took hold of him and successfully lured him away.

8. “Changes” by Tupac, Talent

The moral message in this song is so moving and empowering that it reminds me of the works of some of the greatest artists in history, such as Beethoven and Tolstoy. While the German composer and the Russian author were aristocrats who sympathized with common people’s struggles, Tupac himself was born and raised in the ghetto. The rapper’s perspective is refreshing and inspiring. There is no victim mentality in this song, but only strength, optimism, and a profound sense of hope. By saying “I see no changes”, he is confessing his commitment to not settling with the status quo.

7. “Ratha Be Ya N****” by Tupac, Richie Rich

This musically amusing and pornographically provocative masterpiece reveals a much less serious side of Tupac. There are numerous other Old-school rap songs that explore similar themes, but none of them come even close to this song in terms of musicality and authenticity. It is indeed quite strange that Tupac still comes across as noble and sincere in this song even when he gives graphic details of casual sexual encounters and brags about being a “player” proudly and unapologetically.

6. “Only God Can Judge Me” by Tupac, Rappin' 4-Tay

The magic of Tupac’s music lies in the unique musicality of his rap. He was one of a handful of people who truly understood the essence of rap as an art of the human voice. This song is an excellent example of his unparalleled genius as a rapper. In this song, you cannot find the kind of rhythmic complexity that a New-school rap song would have. Any sort of “fancy tricks” such as fast rap or special vocal effects are also totally absent. What you have is just the true essence of rap in its purest and noblest form. Each single line of his rap in this song is incredibly clear, engaging, and bursting with emotional power.

5. “Hit 'Em Up” by Tupac, The Outlawz

Extremely aggressive yet effortlessly graceful and amusing. The monologue toward the end is an ultimate demonstration of the cathartic power of Hip Hop, which is not about mindless madness but righteous anger. Because of his noble and earnest nature as a person, Tupac’s rap never comes across as vulgar or “filthy” even when he curses for 2 minutes straight. Moreover, while doing so, he is still able to maintain the highest level of artistry. In other words, nothing in his music exists merely for the sake of emotional expression. His music is always flawless musically no matter how “reckless” or “out of control” his expression can be. On the surface, the immense anger in this song is aimed at his enemies. On a deeper level, his anger resembles the kind of divine “rage” in Homer’s poems. Tupac is like a Greek hero compelled to disturb the order of the universe, a crime punishable by death.

4. “To Live and Die In L.A.” by Tupac, Val Young

What a heartwarming and lovely masterpiece! I was a 15-year-old high school kid in Beijing when I first heard this song. I fell in love with it immediately, because his love for L.A. somehow echoed my own feelings toward my hometown. This song is so bright and relaxed that I can almost feel the California sunshine coming through it. Beijing in the summer is also a bright and relaxed city just like L.A. However, instead of “living and dying in Beijing”, I left my hometown and came to the U.S.

3. “Life Goes On” by Tupac

A timeless masterpiece that is immensely sad yet profoundly uplifting. The loss of a dear friend is disheartening, yet happy memories of the past will last forever. The calmness of his voice does not constrain this song’s emotional power but only delivers his heartfelt emotions with greater depths. Once again, this song reveals just what a genuine, pure-hearted, and loveable young man Tupac was, which is why it truly saddens me to think of his early death and the self-destructive path that he slipped onto during his final days. If I could time-travel to meet Tupac, I would say to him: “Don’t you remember what you said in your song? Put a stop to your madness and nonsense, and life will go on.”

2. “Dear Mama” by Tupac

Arguably the greatest emotional masterpiece in the history of Hip Hop. The expression of gratitude, which is the central theme of the song, is simple and relatable. However, only a sincere and talented person like Tupac can express it so movingly and thoroughly. His voice in this song is also calm and full of warmth.

1. “California Love” by Tupac, Dr. Dre

The greatest rap song ever except my own works. Not much needs to be said about this song. If you have no feelings for this song, you simply do not have the ear for Hip Hop. Tupac’s verse in this song is arguably the greatest 16 bars of rap ever composed and recorded. “Out on bail, fresh out of jail, California dreamin'...... From Oakland to Sac-town, the Bay Area and back down. Cali is where they put their mack down. Give me love!” Wow. Just wow.

The existing history of Hip Hop can be divided into two golden eras: the age of Tupac (1992 - 1996), and the age of Eminem (2000 - 2005). There have not been any important rap songs in the past 15 years. Is it the end of the story, or only a prelude for the future?

September 17, 2020