17 Artists on Their All-Time Favorite Rap Songs

In celebration of hip-hop’s 50th anniversary, Lil B, Black Thought, Amaarae, E-40, DJ Drama, Maxwell, and more go deep on the rap songs they love most.
Photos courtesy of Getty Images. Art by Chris Panicker

On August 11, 1973, Cindy Campbell threw a back-to-school party at 1520 Sedgwick Avenue in the Bronx. Her brother Clive, better known as DJ Kool Herc, was enlisted to DJ, and he used the occasion to try out a new technique behind the decks. Quickly flipping between two copies of the same record in sync with the beat of the song, he elongated a funky instrumental section until it became a new piece of music unto itself. A friend who went by Coke La Rock took a microphone and began calling out the names of people at the party, eventually embellishing the shoutouts with simple rhymes. It was the beginning of what we now know as hip-hop.

The genre has branched in many different directions over the last five decades, picking up plenty of new regional flair and musical innovation as it spread across the U.S. and eventually the planet. To celebrate its legacy, we spoke with 17 great artists from inside and outside of hip-hop about their all-time favorite rap songs. Some chose golden-age classics, others more contemporary hits; some gravitated toward personal memory or historical influence, others just wanted to talk about a particularly dope beat or mind-expanding verse. No matter the rationale, these songs changed lives, offering companionship, inspiration, and new ways to understand the world. –Andy Cush


I was in middle school when Kane dropped “Half Steppin’.” He was the quintessential guy at that time in the late ’80s: He had three cuts in his eyebrow and the three-piece suit; he’s got cash on deck, he’s got his ladies. But it wasn’t really a pimp vibe. He was just a well-dressed dude, you know? That did a lot for people in my community.

He changed how people did things. As much as hip-hop is about the actual songs, it’s also a lifestyle, and there was something so magnetic about him. People put cuts in their eyebrows to be like him—years later, Jay-Z had that line, “three cuts in the eyebrow, tryna wild out.” When you can get Jay to say that, so many years later? That’s how far-reaching Kane’s impact was.

And dude was in the Sex book with Naomi Campbell and Madonna! He got a little flak for it at the time, but come on man, that’s legendary. He had a Casanova energy going on, but dude had serious respect. He was this ray of light: Who is this Black man killing it right now?


I was 15, and my parents were in the midst of their second divorce. It was a really tough time for me, and every time I would hear this song, it captured an emotion within me that I didn’t know how to express. Kanye is almost not rapping—it’s freeform, and he’s waxing poetic, going from very honest bars to comedic bars to breaking into song.

The Smokey Robinson sample feels like the core of the record. The drums are minimal, and they have hella reverb, and they’re tucked away in the back. It’s on some outer-space shit, the way the record builds. And it has a rock ’n’ roll edge, with a guitar solo by Mike Dean that creates this tension.

The last verse by Rick Ross represents so many different things to me: struggle and opulence. He is raw, emotional. He gives a nod to some of the music he likes and the things that he’s been through. It all comes back to all that we’ve been through, this life that we’re living.

D.M.C. and Public Enemy

Photos via Getty Images


I was going on tour with the Beastie Boys, and Chuck D and Hank Shocklee came to meet us at JFK Airport. Chuck said, “Y’all gotta hear this,” and they gave Russell Simmons and Lyor Cohen a cassette tape of a new record they had just made. This song was so captivating and addictive that Run-D.M.C. and the Beastie Boys would rush to the dressing room after the show and listen to it on my JVC boombox. It wasn’t just a statement about political and social issues—it was a statement about how no motherfuckers could make hip-hop this incredible.

When Jam Master Jay first heard Chuck on “Public Enemy #1,” he said to Rick and Russell, “God has come down from heaven to rock the mic.” This was God putting his foot in every MC’s ass. It was voice, delivery, rhyme, style. What’s beautiful is that Chuck said he created the cadence off of Rakim, the God MC. Sonically, it was the most powerful, ear-catching, aggressive, complete production of a hip-hop record. It was mature and youthful. It was who we were before we started making records.

Too $hort

“The Message” is probably the most important rap song in my life because it changed the direction of how I wrote songs. I was in high school when it came out and I was just writing party rhymes that weren’t really about anything. But after I heard “The Message,” I started telling the story of Oakland. That was the basis of all my songs from that point on. Besides that, it still sounds good today. It never really went the way of becoming a novelty hit or an oldie. That’s still a solid beat, and whenever somebody samples it, it’s a fuckin’ hit again.

billy woods

MF DOOM’s “Red and Gold” (1999)

Operation: Doomsday is a great album that was important in my life, but this song isn’t the first one from it that jumps out to you as a listener. “Doomsday” and “Rhymes Like Dimes” were my favorites for a while, but the longer I had the album, the more I started to feel like this song is at the heart of what it’s all about.

It exhibits all the traits that made DOOM great. There is a conversational aspect to it, but at the same time everything about it is so tight: “I remember when/Last past November when/Clown kid got pounded in with the Timberlands.” In there, you’ve got a crazy rhyme scheme. He’s flipping around how he’s rhyming and how he’s approaching the song with each verse. There’s an improvisational aspect to it in the way he changes the chorus just a little bit each time, which is something that had an effect on me. There’s comedy; there’s pain and hurt; there’s a street edge. But at the same time it’s very thoughtful and spiritual and philosophical. It contains worlds, without a doubt.

Black Thought

Kool G Rap and DJ Polo’s “Men at Work” (1989)

I don’t have a favorite song, but there are songs where, had it not been for what I got from them, I wouldn’t be where I am. One of those is “Men at Work” by Kool G Rap. I paid homage to it in the Roots discography, in a song called “Thought @ Work,” which is inspired by this song’s cadence. I know all the words to this record; Kool G Rap wrote it when he was around 17—at this point, he probably doesn’t know all the words.

Kool G Rap

Slick Rick’s “Hey Young World” (1988)

Every time I hear “Hey Young World,” it gives me flashbacks of hip-hop in its infancy, when I was going to jams and block parties. We were experiencing something that we didn’t know would dominate the world. This song came around as the floodgates started to open, and it’s really the essence of that era: Rick, KRS-One, Big Daddy Kane, Rakim, and myself really putting the battery in everyone’s back. You don’t get Nas, Raekwon, and Ghost without this era. Rick takes me back to a time before the billions of dollars, before the beefs, when all that was of concern was the music. I love how big hip-hop got, but these were the greatest days of my life.

Lil B

T.I.’s “What You Know” (2006)

It’s not even fair to pick one song, but T.I.’s “What You Know” was one of the things that motivated me to be an artist and to be a part of hip-hop, expressing myself. I was genuinely shocked when I heard it, like, What the heck is this? It was the perfect marriage between DJ Toomp’s production and T.I.’s flow. It’s one of them songs like “We Are the Champions,” one of them winners. It hit every frequency that I needed. When I hear it now it brings me back to a different time in my life, before a lot of the social media stuff. This was when ringtones came out; people weren’t talking about A.I. It was a simpler time.

MF DOOM and KeiyaA

Photos via Getty Images


Madvillain’s “Figaro” (2004)

When I was in college, I worked at this record store called Dusty Groove. It was a store for the heads, so I spent a lot of time going through the CD racks and listening. I knew who DOOM was, but I mostly picked up Madvillainy because it was in the Madlib section. The first time I heard “Figaro,” it kind of changed my life. I had never really heard that type of theater and showmanship. DOOM embodied this character, for real, and would still slip in personal stories.

Back then, I was still mainly a jazz player, and thought of jazz as one world, and everything else was separate. But this showed me what that intersectionality could look like. It was almost like a map. It was something I was craving to find, but was having a hard time tracking down.

My favorite line is, “My momma told me blast ’em and pass her her glass of Ol’ E.” My interpretation is that his mom is an alcoholic who still gave him enough fuel to go up against his adversaries. It’s pretty dark, but with a glimmer of positivity that reminded me of my relationship with my mom. In hip-hop, where the gaze of certain consumers and institutions has really commercialized struggle, I appreciate that this song doesn’t shy away from that, but it isn’t a stereotypical rendering of what a struggling Black man should sound like.

E-40 and Kool Keith

Photos via Getty Images

Kool Keith

E-40’s “Captain Save a Hoe” [ft. the Click] (1993)

I first heard this song on the radio in L.A., and I liked how it was laid-back and mixed the Oakland and L.A. vibes together. Anytime I heard the chorus, I would sing it. E-40 is so naturally funny and clever. He’s a break from the average rapper. So many do street talk the same, but E has so many rhythmic tricks and vocal acrobatics. He always comes up with the flyest spin on the usual. He’s kind of like myself: You can’t duplicate his songs.

This is a pimp song but not in a bad way—straight entertaining instead of downgrading. Even the beat is so original. It makes you want to go to Guitar Center and get one of those keyboards that they used back in the day to make those big, plump sounds. It’s soulful, music for a day riding around in Oakland, hitting a bar, and hanging with people who are real.


On the West Coast, they didn’t teach us about Malcolm X and all of that in school. I learned that from X Clan, Public Enemy, and KRS-One. KRS was a teacher and philosopher to me.

I had a ’67 Cougar back in the day, and we used to bump the hell out of BDP. We had all the slap in our trunk, so the boom-boom-boom of the beat went hard. My favorite part of this song is when he’s talking about flipping dope and profit, and says, “I do it once, I do it twice/Now there’s steak with the beans and rice.” This was when crack cocaine hit the streets, and we did what we had to do as a means for survival. He was also talking about how easy it is to get caught up in the materialistic shit. I was from the hood, so I knew all about it. It was such real storytelling. KRS is one of the greatest at that, and I put myself in that category, too. We paint stories with a verbal brush.

Dawn Richard

Missy Elliott’s “Work It” (2002)

Coming from a punk space, there were very few Black women that resonated with me. But then this one woman was genreless. She was hip-hop, but she was so much more. And that’s Missy Elliott.

The cockiness of “Work It” is just so damn good. “I’d like to get to know ya so I could show ya/Put the pussy on ya”—that lyric is all about the ownership of being a woman. The vulgarness. For a woman to be that herself and to say what she wanted spoke to me. It is sexy, but she wasn’t sexualized: She’s fully-clothed, her head backward in the video, arms long, talking sexy. That was dope to me.

9th Wonder

Pete Rock and CL Smooth’s “They Reminisce Over You (T.R.O.Y.)” (1992)

This song has been attached to me all through my life, since its release in the summer of ’92. I was somewhat of a band geek in school. I was learning music theory, but also listening to hip-hop—playing overtures in the daytime, and then using whatever instrument I was playing to replay some of the hip-hop samples that I heard at night. It was “They Reminisce Over You” that made me say, “OK, whatever he does, that’s what I want to do.”

There were events that had to happen for that song to get made. In the late ’80s and early ’90s, jazz was becoming a big sound in hip-hop, after Q-Tip started to sample it; Pete Rock was the new kid, chopping up his own samples. But maybe the biggest event was the death of Trouble T Roy from Heavy D and the Boyz. Since Pete Rock was Heavy D’s cousin, it totally affected him, and he made this song. When my older brother passed three years ago, the song took on a whole new meaning for me.

DJ Shadow and Schoolly D

Photos via Getty Images

DJ Shadow

At that time, it usually took a little longer for East Coast records to reach us on the West Coast. You wouldn’t hear them until maybe six months after they came out. I was a teenager, and I heard “P.S.K.” for the first time on the radio at my grandmother’s house. The beat is what got me: It’s so minimal, with just these huge drum machine sounds and scratching on top of it, and nothing else. I liked how raw it was, how you could tell that DJ Code Money was just doing his scratches live as the song played. Maybe not every scratch is 100 percent technically perfect, but that’s what’s cool about it, that live energy.

Schoolly D’s lyrics were street talk, like a combination of the Last Poets and Richard Pryor. People talk a lot about this song’s lyrical content, with the beginning of gangsta rap, but I think its real legacy is the beat. Later on, people started doing a lot of sampling of hip-hop from this era, to give you something you recognized. And the “P.S.K.” beat shows up on so many other big records.

No I.D.

Eric B & Rakim’s “In the Ghetto” (1990)

In 1990, I thought that, if I was going to be a musician, I wanted to rap—and “In the Ghetto” was the song that made me want to do it. Rakim’s lyrics weren’t just sporadic thoughts jumping around, you could read them and they made sense. You could see the whole world of the song in your mind, the past and the future, no matter where you were at. I’d never heard songs that had me think outside of the perimeter of what I was learning in my neighborhood. It was a big eye-opener, that music can actually say something, and not be preachy, but clever and subtle and informative. And he came with a monotone style, while everybody else was very animated. I’m a laid-back person, so that attracted my personality. It made me think, Here’s a way I can free my thoughts and get my mind out.

When I first started producing, it was about figuring out a way to make music for myself to rap to, rather than music for other people. The beat for “In the Ghetto” was definitely an inspiration, but at that point, I didn’t have the tools to execute something like that. It was a little advanced for me. I didn’t have any cool samples yet. But as I started to make beats for me, Common just started saying, “Let me have that one, let me have that one.” It probably wasn’t until Common got a record deal and I went to New York that I learned about how to execute that style of production, but that all led to me becoming a producer.

Vijay Iyer

Public Enemy’s “Fight the Power” (1989)

My first exposure to “Fight the Power” was in the opening credits to Do the Right Thing, which I rewatched recently. It reminded me of how hard the song is and took me back to what the MC really was: Certainly it was about lyrical prowess, but it was also the act of moving a crowd. It wasn’t just being clever in the verbal sense. It was also the energy. It’s like this person is revealing the inherent chaos and insurgence of the beat itself.

And then the politics of “Fight the Power” are so forthright, and the analysis is so sharp. That line: “Elvis was a hero to most, but he didn’t mean shit to me.” On top of all that, there are these hectic, chaotic, and dissonant layers that give you the feeling of New York City. Living in Harlem, I feel a lot of that energy as soon as I walk out the door.

DJ Drama

The Notorious B.I.G.’s “Juicy” (1994)

It’s universal and universally known, word for word. It epitomizes so much of what hip-hop is about: taking from the old, with that Mtume “Juicy Fruit” sample, and recreating it for a new generation. That’s what hip-hop was built upon.

From a DJ perspective, I love how he shouts out Ron G, Brucie B, and Kid Capri. There’s the influence of legacy in the song, with lines like, “Remember Rappin’ Duke? Duh-ha, duh-ha/You never thought that hip hop would take it this far.” He wrote that line about 20 years into the history of the music. Now, we’re 50 years in and thinking about lines like that from 30 years ago. Now, you can’t believe hip-hop would take it this far.

Interviews by Andy Cush, Jayson Greene, Clover Hope, and Alphonse Pierre