The 10 Best New York City Rap Songs According To Wiki

It’s a Wiki summer in NYC. The rapper, who might embody the spirit of the city better than anyone alive, is positively buzzing these days. When we caught up with him via Zoom video to discuss his stellar 2026 LP, Ancient History, he was perched in Seward Park, a spot he visits every single day.

“I’m always at Seward. I live a few blocks away, so this is my morning routine type shit,” he explains with that famous missing tooth smile. On “Park,” one of many Ancient History standouts, Wiki raps: “A place to start my day off without pain in my heart/ Caught in a sеa of concrete, what thesе streets are/ I need to see some trees even if these trees sparse/ That’s why I went to the park on the bench.”

It’s from this bench that we talk about New York rap, the Puerto Rico day parade two weekends ago, and our shared bewilderment that our beloved New York Knicks have finally won an NBA Championship. “The album dropped on Friday. The Knicks won on Saturday. The Puerto Rican day parade was on Sunday. Everything worked out. It’s perfect timing.”

It only made sense to enlist the connoisseur of all things New York to share his favorite rap songs to ever emerge from the five boroughs. He mostly stuck to classics, but he made sure to shout out some young stars he’s excited about, too. Much like New York legends co-signed Wiki when he was young, he made sure to take some time to do the same. “The homie Liim is so good. He’s so refreshing. I just love what he’s doing,” he explains. “I love Judah Weston, bro! I’m fucking with it. I like it. It got spammed for sure, but I like to see him. He has great energy.”

Hearing Wiki talk about new music is delightful, but there’s nothing like him wax poetic on his all-time favorites from the city. We touch on Dipset, The LOX, and AZ, but Wiki also shines light on some underground legends who rightfully have become New York icons over the years.

On Ancient History, Wiki makes a case for being New York’s best bar for bar rapper. Below are some of the songs that provided the textbook he studied; the ones that led him to eventually master the exam. These are Wiki’s 10 favorite New York City rap songs.

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Masta Ace — “Beautiful”

Wiki: This is just such a feel good song, but it has a New York perspective. I was thinking about this prompt like, ‘Do the songs represent New York or are they by New York artists?’ I wanted to do something in between. It wasn’t necessarily 10 versions of “N.Y. State of Mind,” but I still want everything to feel really New York. This song is from a grown MC, you know what I mean? There’s a grown perspective on everything. Masta Ace is looking at the glass half full. That’s important to me. I’m a Mets fan like you, but this song has that lyric, “Yeah, this is brand new Uptowns still in the box/ This is the Yankees, 10-nothing, killing the Sox.” Even as a Mets fan, I'm like, ‘Dude, it's too New York.’ I love what Masta Ace represents. He’s one of my favorites. He’s an inspiration because he’s kept making music and has grown with the times, but he’s done it in his own way. It doesn’t feel forced.

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Cam’ron — “Triple Up”

Wiki: If you look at the numbers, Killa Season was huge in New York, but it wasn’t as big as Purple Haze because Dipset had left Roc-A-Fella. But “Triple Up” is the ultimate sound of Dipset from this era. The beat is so good and the hook is so New York. What do you say? “Take your ass up the block doggy, the stoop is us.” It’s kind of a sequel to “Double Up,” too. It’s referencing Dipset itself.

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Mos Def — “Life is Real”

Wiki: Black On Both Sides is one of my favorite albums of all time. I was still really young for Black On Both Sides, so I revisited it when I was older. When New Danger came out, I was listening to hip-hop, discovering things on my own. I feel like this album is so ahead of its time. He was dabbling in rock shit. He has this song “Modern Marvel,” and I’ve always wanted to make a song like that. But “Life Is Real” is the one I played back a million times. I could start every day off with that song. “Reach the world but touch the street first.” It’s so good.

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Juelz Santana — “Lil’ Boy Fresh”

Wiki: Dipset is my number one because I came up in that era of New York. That was the sound of the City and you had to be there to know. Someone could be like, ‘Nah, Roc-A-Fella was bigger than Dipset’ or something. Not in the streets uptown. You heard that shit. Then there was the movement, the fashion, everything. I love Roc-A-Fella, but it was not as organic as Dipset. Growing up, I thought all those Philly dudes were just best friends and they all knew each other.

Dipset felt like Juelz was the little homie that we’re bringing up. They were really doing it and making it happen. I love “Lil’ Boy Fresh” because it’s a real New York tale. It’s got some real uptown shit popping. There are a lot of songs that are about bumping up on some selling, hustling and all that, but this one’s so New York. It really paints the picture of uptown in New York City. It feels like a movie. It feels like New York’s Heat.

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Max B — “Picture Me Rollin”

Wiki: It’s great that Max is home. I love it. People are like, ‘Oh, it's not going to be the same.’ I'm just happy. He’s free. I'm happy he’s having a good time and he seems really positive. I'm also really happy that he came out and had French [Montana] because a lot of people will go in and when they come out they don’t necessarily have the proper support. French has been doing his thing since Max has been away. He’s coming back to real opportunity which is just great. It’s not like, ‘Oh fuck, now I'm back in the streets.’

It’s beautiful to see that. I had to put a Max song on here because he brought this vibe in New York, he brought back barbecue music. You could party, you could chill, the old heads could listen to it. You could do your two step and bop, but it’s still barred up. It’s something that was missing in hip-hop. There were joints from that era like “All The Way Up” and there was street rap, but it wasn’t that fun. This is almost our take on LA barbecue music or some shit, but New York as fuck. It’s block party music. “Picture Me Rollin” is a classic Max B joint. It’s hard, but it has a vibe to it.

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Sham Da God — “Dream Chasing”

Wiki: I need to put a Sham Da God song because he was the unsung legend of the LES. I love his flow on this song. The video is also so New York. He’s riding his bike on the project rooftop. I was talking to the homies about putting this list together and we decided I needed to put a Sham Da God song on there just to also let people know. I was semi-familiar with him before he died, but I became a fan after the fact from listening back. A lot of the homies that were tapped in and tuned in, were putting me on. I was like, ‘Whoa, fuck. This guy was so nice.’

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AZ — “City of Gods”

Wiki: If you want to learn how to rap, just listen to AZ, bro. He has one of the illest, most worldly perspectives, but he’s still a New York OG. He’s just that fly. It’s kind of like what I was saying about Masta Ace. He’s got that real grown OG New York perspective where you’re like, ‘Yo, I got to listen to this guy.’ “City of Gods” is sick because it’s another feel good bop, but he’s saying real shit. It was hard to choose between this one and “Gimme Yours.” I'm an AZ head for sure. When I discovered him, I went through all of his albums and I was like, ‘Whoa, what the fuck?’ I discovered how insane he was.

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The LOX — “Fuck You”

Wiki: There’s a lot of feel good bops on this list. I needed some fuck you energy. This is hard, it’s got a fucked up, weird Swizz Beatz beat, and it’s got an energy like, ‘Fuck you, anyone hating on me,’ that’s so New York. The LOX have that energy. Everyone goes crazy on this shit. It’s unapologetic, fuck you hip-hop. Dipset and Ruff Ryders were the biggest movements in New York, but in terms of a rap group, The LOX were the best ever. Period. They held everything together. Remember when they did that battle against Dipset? That shit brought everything back. Overnight, I saw kids learning their bars and learning how to rap.

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Cormega — “American Beauty”

Wiki: Cormega’s one of the best. I don’t like comparing rappers, because there’s not a science to this shit. His voice, his flow, everything. It’s perfect. “American Beauty” is sick because it's his take on the classic ‘hip-hop as a shorty,’ but it’s his perspective on it. His voice, bro. He’s got the New York lisp, and you hear the New York in his voice on that song. It’s unquestionably New York as fuck. I love New York rappers with that lisp. I have it a little bit, too. Same with Big Pun. Hearing that in the voice is the best because you’re like, ‘Aw, dude.’ Cormega’s ultra underrated.

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Ka — “Up Against Goliath”

Wiki: I must have discovered Ka through Roc Marciano, because they were doing shit years ago. He’s one of those artists where I would always listen to the project when it came out. He’s a writer I always looked up to. His concepts, his simplicity, literally everything about it. That whole project that “Up Against Goliath” is on, Grief Pedigree, is so good. Every project has something to dive into. I love the hook. The writing is so crazy, the Biblical references and shit.

He stopped by the Half God listening party real quick. I always wanted to work with him. I know he kind of did his own thing and wanted to work with people he was really close with, which I totally respected. He came by just to say what’s up, show love. He was there, boom, boom, boom, then dipped off. He walked down the street and disappeared on some superhero shit. I was like, ‘Oh shit, it's Ka. He's really that guy.’

Half God was a dope project too because it also attracted people who are really tuned into Navy Blue. Yasiin reached out, too. They listened and we got some respect for that. Getting respect from some of my favorites of all time was like, ‘I’m good. I can keep going. Everything will be all right.’

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Wiki