My Top 5 Favorite RAPPERS of All Time!

Alright, following up on my Top 5 Favorite Rap Groups list, I think I’ll go ahead and list my top 5 favorite solo rappers.

To be clear, unlike most people or websites that try to rank rappers on a list like this, this isn’t meant to be any type of “official” unbiased list, declaring who is the “best.” No matter how you slice it, that is always going to be subjective. I’m not even saying that these are the most skilled or most talented rappers when it comes to lyricism or anything like that. That’s why I specifically used the word favorite, rather than best. I’m not exactly sure who I’d put in the top 5 if I were trying to list whom I think are the best rappers, but I know at least two of the rappers that I put on this list would not be on that list. These are the rappers who, collectively speaking, I enjoy listening to the most. They have a catalog of music and I can pick a ton of their hits that I love to replay over and over. It’s like when I say that the Fast and Furious franchise is one of my favorite film franchises ever, I’m not saying they’re the greatest films, it’s not the Godfather trilogy, but I just love watching them.

So, without further ado, here is my list, with explanations for each. And yes, again, I’m Gen X so most of my favorites are from that era.


#5 WILL SMITH (THE FRESH PRINCE)

Longtime readers of this blog know of my youthful aspirations of being a professional rapper, and when describing my rap style I usually compare it to a combination of two of the rappers on this list, one of which is Will Smith. I was in Junior High when he debuted, at the ripe old age of just 18 himself, along with his partner Jeff Townes as the recording duo DJ JAZZY JEFF AND THE FRESH PRINCE, with the single GIRLS AIN’T NOTHIN’ BUT TROUBLE. A full album, ROCK THE HOUSE soon followed, and I loved his clean-cut storytelling style, which continues in songs like JUST ONE OF THOSE DAYS and DON’T EVEN TRY IT.

Over the next six years the duo would release 4 more albums, all of which either with Gold or Platinum (their 2nd album, He’s The DJ, I’m The Rapper, went 3 times platinum), before Will basically retired from rap to focus on his burgeoning acting career. Then after 5 years, Will would return to rapping, now just as a solo artist under his real name, and released 4 albums that also went either Gold or Platinum (his first solo album Big Willie Style went 9 times Platinum), culminating in 2005’s LOST & FOUND. He’s made hints in recent years about possible returns to rapping, but nothing serious has emerged as of today. Nevertheless, even if he never records another song, he’ll remain one of my favorites.

As I said, a lot of my early rap-style was modeled after his. I also rarely cursed in my raps, and I loved to write funny story-telling raps, and it’s the latter where Smith really exceled and, in my opinion, doesn’t get enough credit for. He could spin a humorous tale of getting into trouble with his parents, but even if his later more club-anthem dance songs, he was still utilizing his storytelling ability to paint a picture in your head with his words, and that’s what I’ve always admired about him.

#4 EMINEM (MARSHALL MATHERS/SLIM SHADY)

“Will Smith don’t gotta cuss on his raps to sell records, well I do
So fuck him, and fuck you too.”

Like most of the world, I discovered Eminem through his first major label release THE SLIM SHADY LP in 1999. And I’ll admit, I did not like him at first. I was one of those hardcore rap fans who thought he was okay, but overrated, and being celebrated and promoted just because he was White. I’ve written before about the Black community’s historical suspicions towards White rappers, and I shared those views, although my older brother was a big fan of his from the start. It was after his follow up album, THE MARSHALL MATHERS LP, came out the next year that my attitude began to change. Listening to songs like STAN and THE WAY I AM I was like, okay, he’s not bad. But then it was the next album, 2002’s THE EMINEM SHOW that helped him finally win me over. Really, it was the song CLEANING OUT MY CLOSET that did it for me. The fact that he was getting so raw and personal about his childhood and his life was so impressive to me. Rapping about his estranged mother, whom he says abused him as a child, and who then sued him for defamation, he said: “But how dare you try to take what you didn’t help me to get?! You selfish bitch, I hope you fuckin’ burn in hell for this shit!” I was like, damn, that’s the kind of personal reflection that I appreciated from Tupac.

So from then on I was an Eminem convert and started paying more attention to his songs and his lyrics, and he definitely is one of the Greatest of All Time in my opinion. The way he puts words and phrases together that you’d never even think of is just amazing to me. I mean, he’ll rhyme Loch Ness Monster with cross-dressed mobster, and I’m just listening like how’d he come up with that? Also, another I thing I used to be was a battle-rapper. Me and other rappers at my school used to battle all the time (I lost my first battle, but never lost after that), it was all in fun, but it was that ability to win that actually turned the tide in my reputation, as I went from being known as a “nerd” (with big feet) to I guess you could say one of the cool kids (although I still hung out with the same friends as before). And the key to my battle strategy was the punchline. At the end of each rap I always tried to have a really good line that mocked the other rapper and got the crowd laughing. That’s how I’d win. And that’s Eminem’s specialty, except he doesn’t just have one ending punchline, he’ll have multiple clever punchlines in each verse in his song.

And there’s the overall success of his career that’s impressive. To date he’s released 11 albums, all of which have gone at least Gold, and most have gone multi-Platinum. Only Jay Z has a comparable record of longevity, which is not typical in rap music, which is primarly a youth-based genre. But Eminem is 47 and still competing on the charts with rappers who are literally young enough to be his children. Like his beef with Machine Gun Kelly a couple of years ago. MGK did a good job with his diss towards Eminem, but when Eminem came back with his response, there was no question who won.

#3 TUPAC

His inclusion on this list should be no surprise, as I have a whole category on this blog dedicated to writing about him. Another contender for Greatest of All Time. What can I say about Tupac that hasn’t already been said in a bajillion articles, books, documentaries and films by people much more skilled at writing than myself? This young man (it’s easy to forget that he was only 25 when he was killed and had only been recording music for just under 5 years at that time) was multi-talented in his skills as a rapper. He could do politically-charged socially conscious songs, hardcore gangsta raps songs, progressive love songs, and fun party songs all equally well. While some critics charged him with being hypocritical or inconsistent, as he would praise the virtues of Black women in one song and then trash talk “bitches” in the next. But I came to see it as him being real. The fact is that most of us are not binary in our thinking, we have many sides to us. Like, yes, I can believe in the equal rights of women and also like to watch porn. Sometimes I’m in the mood to rant about racism in our society, and sometimes I just want to relax and have fun. It’s not all one or the other. And that’s why Tupac expressed through his music.

There’s also the known fact that he was so fast in terms of his ability to write, being known to record three songs a day sometimes. And that he recorded so much music during this life that seven albums of material, several of which were double albums, were released after his death, is also astounding. And those albums were still hits. LOYAL TO THE GAME, an album released 8 years after Tupac’s death still went Platinum. And these were the songs he didn’t deem good enough to release when he was alive, so it’s easy to imagine that if he’d lived (and managed to stay out of trouble) he would have still continued making great music and dominating the charts well into the 2000’s. He’d be turning 49 this year, I wouldn’t doubt that he’d still be putting out hits album just like Eminem and Jay Z do today (and likely starring in hit movies, like Will Smith). And I can also imagine that he’d have a LOT to say about the social unrest that’s gripping the nation today.

#2 RAKIM

Now this pick IS based on lyrical skill. If that was all this list was based on he would be #1. In my opinion he is the single Greatest Rapper of All Time, and probably always will. Rakim debuted in 1986 as part of the duo ERIC B. AND RAKIM (back then the DJ’s tended to get top-billing in rap duos, same as with Jazzy Jeff and Fresh Prince). When Rakim came on the scene there was just nothing like him. As a rapper at the time, I can tell, he changed the way many of us thought about rapping. Before Rakim, raps were pretty straight-forward, you would have two lines, know as a “bar”, where the last word in the first and second lines would rhyme with each. Sometimes you could keep it going with a third or fourth line with another rhyming world. Example, this classic RUN-DMC verse:

I’m the King of Rock, there is none HIGHER!
Sucker MC’s, should call me SIRE!
To Burn my Kingdom, you must use FIRE!
I won’t stop rockin’ ’til I RETIRE!

Compare that to these lines from ERIC. B AND RAKIM’s debut single ERIC B. IS PRESIDENT:

I made it easy to dance to this.
But can you detect what’s coming next from the flex of the wrist?
Say indeed and I’ll proceed ’cause my man made a mix
If he bleed he won’t need no band-aid to fix

Now you notice how he follows the traditional style of (mostly) rhyming the last words in each line, even making sure all four sound similar? THIS, WRIST, MIX, and FIX. But then he also rhymes three words in the second line before then end. DETECT, NEXT, and FLEX. And then in third line he rhymes INDEED and PROCEED, and in then in fourth line he rhymes BLEED and NEED. It’s pretty complex for it’s time, but his vocal flow is natural is sounds effortless. Like I said, this was a new way of rhyming. And after that, we were all trying to rhyme like that.

In fairness, Rakim wasn’t the only one showcasing this new style, his contemporaries KRS-ONE and BIG DADDY KANE who soon followed him were also masters of this style and helped popularize it. But, in my opinion, Rakim was definitely the best and is the most influential. .

Last year Rakim published his autobiography SWEAT THE TECHNIQUE where he not only recounts the highlights of his personal life and professional career but also goes into detail about his rapping and songwriting style and how it evoled over the years, and I’d highly recommend it to any rapper of rap music aficionado.

#1 LL COOL J

James Todd Smith aka Ladies Love Cool James. My favorite rapper of all time. He made his first professional record at just 16 years old, releasing the single I NEED BEAT, the record that launched the legendary rap label DEF JAM. At 17 he released his debut album RADIO, which I still consider a classic, and I’ve been a fan ever since. As I said in the beginning, there were two rappers I’ve compared myself to, and LL is the other one. I’d say I was mix of LL Cool J and The Fresh Prince, most of my raps were either telling funny stories (like Fresh Prince) or bragging about how good a rapper I was (like LL Cool J).

LL was also influential in several ways. He was one of the first rap acts to actively appeal to girls, not just try to be hard and tough for the dudes. There was the rap group WHODINI before him who also did that, but LL was more of a teen idol. And he was the first rap act to do a flat-out love song. He had the tracks I WANT YOU and I CAN GIVE YOU MORE on his first album (and Whodini had released the mellow track ONE LOVE in 1986), but it was on his second album, 1987’s BIGGER AND DEFFER, that he released I NEED LOVE, the first real rap ballad. After that, every had rapper had to have a long song on their albums. There were so many I Need Love knock offs, like M.C. Shan’s LEFT ME LONELY, Slick Rick’s TEENAGE LOVE, and Vanilla Ice’s I LOVE YOU.

But I’d also say his biggest influence was just being a solo rap star. There’d been other solo rappers with hits, of course, like Kurtis Blow, but rap music was still dominated by groups, or duos of a DJ and a rapper. And that’s what most of us young aspiring rappers wanted to be in. We were all forming groups to rap together (mine was “The Hardcore Four”). But after LL came out that changed, and it became more about just getting known as a rapper yourself, you fantasized about getting your own record contract, not signing one with your friends. The fact that LL was still a teenager, closer to our age than the other big rap acts, also made him seem more relatable. I mean, the FAT BOYS were teenagers too, but they were a slapstick gimmicky group, I don’t think anyone really wanted to be them, the way we would later want to be LL. When Tupac was nominated the Rock N Roll Hall of Fame in 2016, Chuck D caused a ruckus on the internet when publicly stated that no solo rapper should be inducted into the HOF before LL Cool J, for this very reason. And he’s still right!

LL Cool J forever, y’all!

3 comments

  1. Did you hear will smith on the remix to “will” by joyner lucas that was put out recently? Even I was impressed that the boy had some skills. He was always known for his clean rap but I never really considered his one of the best. But listening to that remix, yeah, he’s definitely up there. I too didn’t like eminem at first but that was due to my own bias. After really listening to him the dude really got some thought provoking stuff that comes out of that head. Also I like how he is so open about his own issues like drug addiction. I can’t think of anyone who could face him lyrically. I’ve discussed LL before and yeah he definitely has that appeal for the masses for what it is worth. Can’t gloss over the fact though he got eaten up by Canibus back in the day but look at who’s still around and who is not. Canibus won the battle, LL won the war. Rakim, I knew of him and some of his stuff was quoted and copied by other rappers but I just neve got into him. Tupac…what more is to say…”got money for wars but can’t feed the poor”. Even during that whole east and west coast beef thing I just could not stop listening to him. What even surprised me was that he appealed to my older sister who I thought of as a conservative type but as you stated he talked about political issues that people, most of them people of color were facing.

    Liked by 1 person

    • Yes, loved the “Will” remixed, he’s still got it! But remember, I make a point of stressing that this isn’t necessarily about who’s the “best” lyrically-speaking. Honestly, it’s two different things. There’s plenty of women with better singing voices than Madonna and Beyonce, but not many who have as many hit songs. Likewise, the ability to rap really well, and the ability to write great rap songs are not always the same. Sure, rappers like Eminem and Rakim can write big hits that have complex and witty lyrics but there’s far more rappers who’ve had major hits with “average” (or worse) lyrics. Remember how big Hammer was back in the day, and he could barely rap. A lot of rappers today are making hits with a catchy beat, a catchy chorus, and a creative video.

      So yeah, I agree that technically Canibus is a better rapper than LL, I’ve listened to tons of his freestyles on Youtube, but he just hasn’t been able to craft anywhere near the number of hit records. Even back in LL’s prime, Kool More Dee outclassed him in back and forth battle-songs but, again, who has the longer career with a bigger catalog of hits? Ultimately I think that’s what really matters. So when it came time to compile this list, I just sat and thought about what songs I like to listen too most often, and these are the 5 who have the most songs on that list.

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