I saw Chris Rock’s Top Five last weekend and the question, “What’s your Top Five?” comes up throughout the movie. Ever since, I’ve been trying to make my own Top Five MCs list, something I’ve failed at in the past. Why? I have nine rappers I want to include. But today, once and for all, I'm going to make my Top Five.

First, there’s Biggie, Jay Z, and Nas. For most rap fans of my generation who grew up in New York—I went to high school from 1992 to 1996—Biggie, Jay Z, and Nas are the Three Kings. Beyond their popularity and impact on the genre, they’re all ridiculously dope MCs and charismatic human beings with loads of classic material. It feels disrespectful not to include them after all they’ve given to me. But including all three right off the bat instantly clogs up my list. Before I’ve even started, I’m left with just two slots to fill.

Which brings me to my next grouping of MCs: Redman, Ghostface Killah, and Prodigy—the grimier versions of Biggie, Jay Z, and Nas. (I’m a rap fan who appreciates grime over shine.) Biggie, Jay Z, and Nas are dope, but Redman, Ghostface Killah, and Prodigy are ill, and yes, there’s a difference. They’re wilder, less polished, darker, and crazier, both bars- and personality-wise. I like my favorite rappers to be a little unhinged. So maybe I should start with those three as my definites?

List so far: 

Redman
Ghostface Killah
Prodigy
TBD
TBD

Biggie, Jay Z, and Nas are dope, but Redman, Ghostface Killah, and Prodigy are ill, and yes, There’s a difference.

Redman was my favorite rapper when I was in high school, but everything I listen to now comes from his 90s output. But that 90s, “Tonight’s da Night” Redman shit is so potent that it might outweigh Jay Z’s longevity, even when you consider 21st century gems like “Allure.” It’s a hard comparison, because they’re very different MCs. How do I compare Dare Iz a Darkside to Reasonable Doubt? It comes down to personal preference. And in the end, I have to take Redman. I prefer his weed-infested, gymnastic raps over Jay’s drug dealer tales. That doesn’t mean he’s off the list. He’s just not in my Top Three.

List so far: 

Redman
Ghostface Killah
Prodigy
Jay Z
TBD

OK, let me pit Biggie against Ghostface. Biggie has an unfair disadvantage because he was killed at a young age, with only two albums released in his time. But those few years before his death were special. I still remember the first time I heard “Unbelievable.” Anyone who grew up in New York during the mid-’90s can vouch for how exciting everything that he dropped was when it first came out. A new Biggie song was like crack.

Ghost, on the other hand, has crazy longevity. His verse on Mobb Deep’s “Dirt (Remix)” was one of my favorite moments of last year. And between Ironman, Supreme Clientele, Only Built 4 Cuban Linx…, the first two Wu-Tang Clan albums, and all the other dope LPs and songs and features since, he’s too consistent. As dope as Biggie was, nothing he released excited me more than Ghost’s performance on “Wisdom Body.” So Ghost stays in my Top Three, and B.I.G. moves into my fifth spot.

List so far: 

Redman
Ghostface Killah
Prodigy
Jay Z
The Notorious B.I.G.

Now, Queensbridge’s finest: Nas vs. Prodigy. Prodigy has always been a personal favorite. The guy can deliver a bar that doesn’t even rhyme and it will still kill. And I enjoy his new shit, 20 years later. “Stay Dope,” from Albert Einstein, proves that he will never lose it. I love his voice, his choice of beats, his lyrics, his flow—hell, even his autobiography is amazing. Plus Mobb Deep’s The Infamous and Hell on Earth are both untouchable, and his solo career is riddled with fire like Return of the Mac.

But can Prodigy really take out Nas? No. Nas has more songs I love than any other rapper. Illmatic and It Was Written are classics. Songs like “2nd Childhood” and “Nazareth Savage” are next level. His verse on “Verbal Intercourse” may be the dopest 16 of all time, and on “Eye for an Eye” he murdered P on his own shit. He’s still going, too. “The Season” is one of my favorite songs from 2014. They both are QB legends, but Nas takes the cake. My bad, kicko. It’s close, but I gotta put Nas back in my Top Three, and move Prodigy out of the Top Five.

List so far: 

Redman
Ghostface Killah
Nas
Jay Z
The Notorious BIG

I’m making progress. But wait! I’ve still got three other rappers I want to put on the list!

Here’s where it gets tricky. Where do my current favorites stand? Can they take out MCs who’ve been doing it since the 90s, the ones I grew up listening to? Can their smaller body of work knock out older guys with decades of classics? It’s possible, especially with rappers like Action Bronson, Roc Marciano, and Kanye West.

I wrote an article a couple years back proclaiming Action Bronson my favorite rapper of all time. He still is. That doesn’t mean I think he’s the nicest rapper of all time, or has the strongest catalog—it simply means he’s my favorite. I connect with him on a personal level. Being a Jewish rapper from New York myself, I relate to his music, persona, and humor in a different way, more than any other rapper I know.

Where do my current favorites stand? Can they take out guys who’ve been doing it since the ’90s, that I grew up listening to? Can their smaller body of work knock out older guys with decades of classics?

With Bronson, I have to explore the criteria for making my Top Five even more. Does he make it over Nas because of personal connection? What about the music? Nas made Illmatic and It Was Written, but if I had a choice right now, I think I’d rather listen to Rare Chandeliers and Blue Chips 2. It’s just a different type of entertainment, like choosing Wedding Crashers over Goodfellas. They’re both excellent, but which one do I prefer? Which one speaks to me more?

I’m in a similar debacle with Roc Marciano, who I think is the best rapper alive. His albums and guest appearances in the past few years are absolutely unfuckwittable. Everything he’s put out in his career is a modern classic, including loosies on his SoundCloud page. As a live performer, he is absolutely godly. He’s truly a master of ceremonies with the mic. But can he really knock Biggie or Jay Z off my list?

Finally, there’s Kanye West. If there’s ever been a rapper with the complete package, it’s him. He makes classic albums, hits, and he rips verses. He’s interesting and he’s relatable. He pushes the genre forward, and he puts on a dope live show. Hov against Kanye is a tough match, but to me, Jay’s close to the end. Magna Carta ... Holy Grail wasn’t great, and other than his “Bitch, Don’t Kill My Vibe (Remix)” verse, I haven’t been loving his recent guest appearances. And to me, “Devil in a New Dress” is doper than anything Jay’s done in the past 10 years. Watch the Throne was pretty even bar-wise, but I dig Kanye’s style over Jay Z when it comes down to it.

List so far: 

Redman
Ghostface Killah
Nas
The Notorious B.I.G.
Kanye West

Now I’m gonna make a bold move real quick and put Roc Marciano in the Top Three right now over Redman. He’s too fly with it, and has too much potential. I’m checking for everything he does, whereas Redman’s more miss than hit with me right now. As for Action, based off personal connection and my deep love for his brand of rap, I gotta squeeze him in. So who’s gonna fall? I think Kanye is amazing. But if it’s between keeping Ye or Nas, Kanye gotta go. Nas is too legendary, and his catalog is too deep.

List so far: 

Nas
Ghostface Killah
Roc Marciano
Action Bronson
TBD

I got one more slot. Fuck it, I’m putting Redman back on. He’s my sentimental pick, the one my younger self insists is on the list. My all-time Top Five needs some youthful spirit.

I almost forgot. My Sixth Man. This was something Chris Rock added to his list in the movie that I thought was fun. I’m gonna come out of nowhere and bypass all my other choices with a sleeper, because it’s my list so why not. Peedi Crakk!!! The mac go rrrrrrinngggg!!! Dude never released a proper solo album, but I’ve always loved his energy and State Property swag. He’s my favorite mixtape rapper, one of the rawest, most underrated spitters alive. Ask the Roots, they know what’s up.

OK! So here’s my Top Five, in no particular order, plus my Sixth Man.

Final list: 

Nas
Ghostface Killah
Roc Marciano
Action Bronson
Redman

6th man: Peedi Crakk

That was tough. But I must say, it looks good, it feels good, and it makes sense—to me. That’s all that matters.

So...who's in your Top Five?

Daniel Isenberg is a writer living in Westchester County, New York. You can follow him on Twitter here.