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ip-hop is an art form that rewards style and originality yet constantly pays homage — through samples, shout-outs and collaborations — to the artists on whose shoulders it stands. As Aug. 11 approaches — 50 years from the day DJ Kool Herc threw a 1973 back-to-school party for his sister Cindy at 1520 Sedgwick Ave. in the Bronx, widely regarded as the birth of hip-hop — we could have made a ranked list you’d argue about. But no top 50 can encompass all that this form of cultural expression has become, or include everyone who has played a part in it.

With that in mind, we asked people who made the music we love to tell us about songs they love — the ones that still make them feel the way they first did, or those that inspired, impacted or influenced them. We talked to hip-hop figures from various eras and regions, including a few non-artists, looking for anything but standard answers. In short, we passed the mic to hip-hop and let it freestyle. By having artists share what they love about hip-hop — its beauty, its insight, its unapologetic nature — we hope they’ll remind you of what you love too, or introduce you to songs you’d overlooked.

Listen to the 50 songs as you scroll, by toggling the sound on and off, or enjoy them as a Spotify playlist here. You might, of course, encounter explicit lyrics. In a separate essay, Post music critic Chris Richards reminds us not to forget the past 20 years as we celebrate hip-hop’s 50th. And, in a reminder that music is universal, take our quiz on the unexpected songs loved by artists such as Ice-T, Uncle Luke and Masta Ace. Lastly, you won’t want to miss a special episode of “Post Reports” on Aug. 11, telling hip-hop’s story through new interviews with Rakim, Yo-Yo and Drumma Boy, among others.

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All 50 songs
Songs
Picked by Too $hort
Picked by Too $hort

The Message

Artist: 

Melle Mel and Duke Bootee

Album: 

The Message

Year: 

1982

“The Message” is often credited with stretching what hip-hop could be — not just party music but also social commentary. Big Daddy Kane, Daddy-O of Stetsasonic and longtime hip-hop promoter Charlie Mack each told The Washington Post that the song — recorded in 1980 by Furious Five MC Melle Mel and Sugar Hill Records session musician Duke Bootee, and rereleased in 1982, when it became a huge hit, with Grandmaster Flash and the Furious Five on the label — is one of the best ever recorded. But it was Too $hort whose praise of the song captured our attention.

“I was a rapper before ‘The Message’ came out. And everything about that song changed me. It changed the way I thought about hip-hop, the way I thought about doing hip-hop. As a rapper from that point on, I knew what I wanted to rap about,” he says. Before hearing the song, Too $hort said he was “mimicking” other music. “But when ‘The Message’ came out, I started writing songs about Oakland. I remember thinking to myself, I’ve never been in New York City. ‘The Message’ made me feel like it was my first time going to New York City. Like I actually could see New York listening to that song. And I wanted people to see Oakland, so it gave me that direction. And I’ve never wavered since.”

Too $hort also picked “I’m Your Pusher” by Ice-T.

A hip-hop pioneer who rose to fame selling custom-made tapes in Oakland, Calif., Too $hort has put out more than 20 albums and hosts a show on SiriusXM’s Rock the Bells. His hits include “Blow the Whistle,” “Freaky Tales,” “The Ghetto” and “Gettin’ It.”

Picked by Ed Lover
Picked by Ed Lover

6 ’N the Mornin’

Artist: 

Ice-T

Album: 

Rhyme Pays

Year: 

1987

“When we heard ‘The Message,’ you smelled the Bronx, New York, you tasted what was going on. It was that vivid to you. ‘6 ’N the Mornin’’ was like, ‘Oh, that’s what’s going on the West Coast?’” Ed Lover recalls. “Nobody knew it. Then N.W.A. came; Ice-T opened the door for them to do what they do. That’s what I was talking about. I can smell it. I can feel it. I can taste it. It was real. And a lot of people around the country were going through the same thing, so they could smell it and feel it and taste it too. It was no bragging rap. It was reality rap.”

Ed Lover hosted the daily hip-hop video show “Yo! MTV Raps” alongside André “Doctor Dré” Brown from 1988 to 1995. He has been a constant presence on the airwaves since, and is currently a nationally syndicated host for Audacy.

Picked by Kurtis Blow
Picked by Kurtis Blow

Rapper’s Delight

Artist: 

Sugarhill Gang

Album: 

n/a

Year: 

1979

Wonder Mike, Master Gee and Big Bank Hank — the latter with rhymes penned by the Cold Crush Brothers’ Grandmaster Caz — shook up the world with hip-hop’s first radio-friendly smash hit. The very first words — “I said a-hip, hop, the hippie, the hippie to the hip-hip-hop” — caught on, and the song, set to the bass line of Chic’s “Good Times,” was exactly what the title promised: a delight.

“That was a monumental song, for everyone,” Kurtis Blow said. “I remember that summer of ’79, every car driving up the block, every bus, every train, every boombox, every radio station was playing that song.”

It inspired Blow to shop “Christmas Rappin’,” which he considers the fourth hip-hop record ever made. For countless other artists, “Rapper’s Delight” was the moment they realized hip-hop had no limits.

“It got us to a point where we got serious about making records,” Scorpio of the Furious Five said. “We were used to doing parties for four hours and didn’t want to condense that to four minutes.”

Kurtis Blow became one of hip-hop’s first superstars and the first rapper signed to a major label. “Christmas Rappin’,” “The Breaks” and “If I Ruled the World” endure as classics.

Picked by Fat Joe
Picked by Fat Joe

Vapors

Artist: 

Biz Markie

Album: 

Goin’ Off

Year: 

1988

When Fat Joe was a teen, he first heard the song in which Biz Markie describes changes in attitude toward him and his friends after success. “It’s never changed. My favorite hip-hop song has never changed for the last 40 years,” he says. “Me growing up in the Bronx, growing up with nothing, not having much to eat, not having anything in reference to fly clothes, or anything like that, it was the soundtrack to my life. I worked hard to get money, and come up, and everybody who made fun of me, I would play this song, ‘Vapors,’ for them.”

Fat Joe rose to prominence as a member of the Diggin’ in the Crates Crew. He helped launch the career of Big Pun and is known for hits such as “What’s Luv?” featuring Ashanti and Ja Rule and Terror Squad’s “Lean Back.”

Picked by Mike D
Picked by Mike D

Me, Myself & I

Artist: 

De La Soul

Album: 

3 Feet High and Rising

Year: 

1989

“I’m going with De La Soul’s ‘Me, Myself and I,’” Mike D says, noting the song is tied with Public Enemy’s “Rebel Without a Pause” as his all-time favorite. When the Beastie Boys were working on “Paul’s Boutique,” they listened to an advance copy of the De La Soul record, Mike D recalled. “There was this exhilarating feeling. Our minds were blown. And at the same time, we were enraged with jealousy,” he says, laughing. “Because we felt like we had been working on ‘Paul’s Boutique’ at that point for months and months, or even years at that point, and especially with De La Soul, we’re like, ‘These guys get it. This is what we wanted to do!’”

“[‘Me, Myself and I’ producer] Prince Paul and De La showed the world what is possible when you can combine samples of musical genres from all over and make something that’s totally uniquely yours — and something that’s never been done before. It’s totally mind-blowing.”

Mike D also picked Run-DMC’s “Sucker M.C.’s.”

Mike D and his fellow Beastie Boys came into hip-hop as brash party rhymers and some of its first White stars. Over several albums, they mastered live instruments, stretched genres, penned thoughtful lyrics and became Rock & Roll Hall of Famers.

Picked by Yo-Yo
Picked by Yo-Yo

Doo Wop (That Thing)

Artist: 

Lauryn Hill

Album: 

The Miseducation of Lauryn Hill

Year: 

1998

“The album that inspired me the most as an artist was the Lauryn Hill album. When she came out with ‘The Miseducation of Lauryn Hill,’ that inspired me a lot because hip-hop was at a change,” she says. “When I came in, it was one way, and then I was trying to create another way. And then she came with just all that I wanted to say at that time. I was thinking how to say it, and she said it so well. So that album really inspired me.”

Yo-Yo also picked “California Love” by 2Pac featuring Dr. Dre.

Yo-Yo pioneered West Coast female-empowerment hip-hop when she debuted alongside a newly solo Ice Cube in 1990. She hosts “Downright Delicious,” a cooking show on AspireTV.

Picked by Common & LL Cool J
Picked by Common
Picked by LL Cool J

Shook Ones, Pt. II

Artist: 

Mobb Deep

Album: 

The Infamous

Year: 

1995

“I just love the vibration of that song,” Common says. “It just feels so hip-hop, so pure and raw. It has a certain high-quality level of artistry that I just feel hip-hop possesses. Anytime I heard it and hear it, it just makes me feel like I can do anything. And that’s what hip-hop really gave me. And that song embodies it.”

LL Cool J, like many artists we talked to for this project, says he loves the whole genre of hip-hop and found it hard to pin down one standout song. “My mood changes depending on what’s going on at that particular time. Sometimes I might be in a ‘Shook Ones’ mode, sometimes I might be in another mood.”

Common is a Chicago-born MC, poet and actor associated with neo-soul and “conscious” hip-hop. The frequent J Dilla collaborator has been equally comfortable alongside Nas or Canibus or going at Ice Cube. He has won an Oscar and an Emmy.

The “G.O.A.T.” LL Cool J had early success with the Def Jam label, crossover appeal with “I Need Love” and some legendary battles. He later branched out into TV and movies and has a branded Rock the Bells station on SiriusXM.

Picked by Jim Jones & Layzie Bone
Picked by Jim Jones
Picked by Layzie Bone

Tha Crossroads

Artist: 

Bone Thugs-N-Harmony

Album: 

E. 1999 Eternal

Year: 

1995

Bone Thugs-N-Harmony introduced a melodic style of tongue-twisting rapping when they broke through on “Thuggish Ruggish Bone,” but “Tha Crossroads” is held in high esteem for the way it tugs on the heartstrings. It’s “a song that’s about something that goes on every day and goes on for eternity, which is death and losing people,” Layzie Bone says of his group’s hit. “That song became brand-new for me when I lost my mom, so I connected with it again because of that process of life.” The song also reminds Jim Jones of a parent — his mother, Nancy, who is best known as Mama Jones on TV’s “Love & Hip-Hop.” “That’s me and my mother’s favorite song. We love to listen to it,” he says.

Jim Jones rose to fame on the mic alongside Cam’ron as part of the Diplomats and more recently as a reality TV star on the VH1 series “Love & Hip Hop.”

Layzie Bone is one of the five members of Bone Thugs-N-Harmony, considered one of hip-hop’s most melodic groups. The Cleveland group won a Grammy in 1997 for “Tha Crossroads,” their tribute to mentor Eazy-E, who died in 1995.

Picked by Scorpio of the Furious Five
Picked by Scorpio of the Furious Five

Guard Your Grill

Artist: 

Naughty by Nature

Album: 

Naughty by Nature

Year: 

1991

“I like Treach, how he came into the industry and created his own lane, his own rap style, making hip-hop anthems. But it’s not even like the biggest songs, the ‘Hip Hop Hoorays’ and all that. I’m talking about ‘Guard Your Grill’ and all of his deep songs,” Scorpio notes. “As a hip-hop head, sometimes you just get in that zone where you want to wild out, you want to be not politically correct. Treach is the one that does it for me.”

Scorpio is one of the Furious Five, the pioneering group of MCs that rapped alongside Grandmaster Flash. He still performs with Melle Mel to this day.

Picked by Apollo Brown
Picked by Apollo Brown

Nutmeg

Artist: 

Ghostface Killah featuring RZA

Album: 

Supreme Clientele

Year: 

2000

Apollo Brown recalls how, when he was in college at Michigan State with friend and fellow producer Bronze Nazareth, music store Sam Goody would open from midnight to 1 a.m. to sell the new releases that came out on Tuesdays. “We used to go every Monday to go get whatever we were going to get and get it before everybody else. So we went. We both grabbed ‘Supreme Clientele.’ And this was after hearing ‘Apollo Kids’ and ‘One.’ We’re like, ‘We’ve got to get this album. This album is going to be crazy.’ Got the album. As soon as ‘Nutmeg’ came on, we were like, ‘Yo, I can’t even finish walking back to my dorm room. I’ve got to lay right here on the grass.’ Literally laid right there in the grass, at 1 o’clock in the morning, and listened to this album. And I’ve never had that feeling about an album since, not even my own albums. It’s just that album right there for some reason, gave me this specific feeling that went through my bones and my body and my muscles and my hands and my veins and whatever that I’ve never been able to duplicate ever again. … I don’t even get that same feeling from [Black Moon’s] ‘Enta da Stage,’ even though that’s my favorite album of all time. There’s just a certain feeling that I got from ‘Supreme Clientele’ that I’ve never been able to duplicate. It’s crazy, man. But that’s what I’m always looking for. You know, people always talk about [how] they’re always chasing their first high.”

Brown also picked “Let Me Ride” by Dr. Dre.

Apollo Brown is a prolific Detroit producer known for his work with Ugly Heroes and The Left, as well as behind the boards for O.C., Ras Kass, Guilty Simpson, Planet Asia and Skyzoo, among others.

Picked by Joyner Lucas
Picked by Joyner Lucas

Dear Mama

Artist: 

2Pac

Album: 

Me Against the World

Year: 

1995

“I like that he’s being authentic. I like that he’s telling his truth. I like that he’s fearless,” Joyner Lucas says. “Even though he’s making records talking about how she smokes crack and X-Y-Z, he also praised her and uplifted her. It’s a very deep record. That’s one of the greatest songs ever created, as a storyteller record. It’s just a perfect record.”

Lucas also picked “Stan” by Eminem.

Joyner Lucas, a lyricist from Worcester, Mass., rose to popularity with his single “Ross Capicchioni” in 2015. He was nominated for two Grammy Awards in 2019, for “Lucky You” and the music video for “I’m Not Racist.”

Picked by Homeboy Sandman
Picked by Homeboy Sandman

It Gets No Rougher

Artist: 

LL Cool J

Album: 

Walking With a Panther

Year: 

1989

Homeboy Sandman says he was 9 in 1989 and preparing to perform “I’m That Type of Guy,” the lead single from LL Cool J’s third album, at a summer-camp talent show. But after buying the maxi-single at Queens Center Mall, he ended up listening to “It Gets No Rougher” by accident. He was instantly hooked.

“Immediately I was like, ‘I’m not doing the other jam at all at the talent show,’” he says.

LL had the ability to make songs with wide appeal, such as “I Need Love,” Homeboy Sandman recalls. “But ‘It Gets No Rougher’ is a hard rap jam,” he said. “Just crazy, like ‘if anybody wants to try to out-rap me, let’s do it.’ ... And [LL] can do that with anybody. And when I heard “It Gets No Rougher,” I got so much juice that I scrapped doing “I’m That Type of Guy.” Immediately, he memorized the lyrics to “It Gets No Rougher.”

“And I killed the talent show,” he said.

Homeboy Sandman also picked “Fear Not of Man” by Mos Def.

Homeboy Sandman is one of hip-hop’s most gifted wordsmiths, known for building songs around clever concepts. He has released albums on the respected “underground” labels Stones Throw and Mello Music Group.

Picked by Juvenile & Common
Picked by Juvenile
Picked by Common

My Philosophy

Artist: 

Boogie Down Productions

Album: 

By All Means Necessary

Year: 

1988

Juvenile says the song marks the point when all his friends fell in love with hip-hop: “It was a song everyone could recite together. And it’s still like that. When it comes on, me and my wife, we put our BDP hats on and cut up.”

For Common, “it was influential in a way that introduced me to what being a vegetarian was. It made me see things in a different way or think about the fact that KRS was saying, ‘I don’t eat chicken or turkey or hamburger. ’Cause to me, that’s suicide, self-murder.’ That was a whole new concept to me. I grew up in Chicago, [where we eat] everything. To hear somebody say they’re not eating certain things and I’m like, ‘I wonder why.’ … He was going against all the stereotypes and just trying to raise the consciousness.”

As New Orleans hip-hop exploded in the late ’90s and early 2000s, Juvenile — alongside Cash Money Records cohorts Lil Wayne, Birdman and Mannie Fresh — found nationwide success with “Ha,” “Back That A-- Up” and “Slow Motion.”

Common is a Chicago-born MC, poet and actor associated with neo-soul and “conscious” hip-hop. The frequent J Dilla collaborator has been equally comfortable alongside Nas or Canibus or going at Ice Cube. He has won an Oscar and an Emmy.

Picked by Greg Mack
Picked by Greg Mack

F--- tha Police

Artist: 

N.W.A.

Album: 

Straight Outta Compton

Year: 

1988

Fat Joe recalls the initial punch of hearing this searing N.W.A. rebuke: “The first time I ever heard that song, it was just right in our faces, like ‘boom, this is what it is.’”

Greg Mack said he supports law enforcement but that he recognized the power that N.W.A. wielded by shining a light on what it felt was police injustice. “The thing about the way Ice Cube wrote that song and explained what was going on in the community and what we as Black men were dealing with, it was so on point,” he says. Mack said he would frequently get pulled over in his Cadillac with his wife or business acquaintances and get accused of being a pimp.

“When the movie ‘Straight Outta Compton’ came out, I had some sheriffs approach me. They weren’t very happy that I was portrayed in it because they don’t like N.W.A. But it’s because they didn’t really understand what was being said.”

At KDAY 1580 in Los Angeles in the early ’80s, Greg Mack became one of the first radio DJs to play hip-hop, launching the careers of several luminaries. He has been on the air 48 years and is currently at Audacy’s 94.7 The Wave.

Picked by Statik Selektah
Picked by Statik Selektah

I Used to Love H.E.R.

Artist: 

Common

Album: 

Resurrection

Year: 

1994

Statik Selektah first heard the song, an extended metaphor about the state of hip-hop at the time, as it battled commercialism and other outside pressure, when he was young. “It just kind of tells my story a little bit, as far as when I fell in love with hip-hop around 10 years old,” he says. “Just all the emotions in it — the song is talking about a girl, but he’s talking about hip-hop.”

Statik also picked “Code of the Streets” by Gang Starr.

A prolific producer and DJ from Massachusetts, Statik Selektah hosts a show on SiriusXM’s Shade 45 and has released collaboration albums with Bun B, Freeway and Termanology, among others.

Picked by Buckshot of Black Moon & The Alchemist
Picked by Buckshot of Black Moon
Picked by The Alchemist

So Wat Cha Sayin’

Artist: 

EPMD

Album: 

Unfinished Business

Year: 

1989

The video for “So Wat Cha Sayin’” is filmed in the sewer, with Erick Sermon and Parrish Smith dressed in relatively normal clothes, including their signature bucket hats and gold chains. “It wasn’t no MC Hammer going on over there,” Buckshot says, in reference to the flashily dressed, always-dancing entertainer from Oakland, Calif. “They showed me you could be gritty and grungy in hip-hop. It was all about the grime and the rhyme.”

The Alchemist also chose it, saying that “the beat was very unique and it came out in a time when we were very impressionable and just hearing stuff. ... And it was just the epitome of what we wanted to be: the visuals, the style, the beat, the raps. It was a full package of something incredible.”

Buckshot is the lead MC for Black Moon, whose 1993 debut, “Enta da Stage,” gave jazz samples a dark boom-bap sound. He became a pioneer of independent label ownership by putting out Smif-N-Wessun, Heltah Skeltah and O.G.C. on Duck Down Records.

One of hip-hop’s most consistent producers, the Alchemist has provided soundscapes for Mobb Deep, Jadakiss, Dilated Peoples, Action Bronson and Freddie Gibbs. He raps alongside Evidence as Step Brothers.

Picked by Big Tigger
Picked by Big Tigger

Get By

Artist: 

Talib Kweli

Album: 

Quality

Year: 

2002

“That’s an inspiring song. It’s actually one of my alarm songs. I have a bunch of alarms that play when I get up, and the last song when it’s time to leave the house is that one. So I hear that song every day. … The hook helps me get up and get focused for the day. [Kweli] says, “This morning, I woke up. Feeling brand new, I jumped up. Feeling my highs, and my lows.”

Big Tigger also picked “Headbanger” by EPMD featuring Redman and K-Solo, and “Time 4 Sum Aksion” by Redman.

Big Tigger hosted BET’s “Rap City: Tha Bassment” and “106 & Park.” He has spent 30 years in radio and 27 on TV and currently hosts “The Big Tigger Morning Show” on Audacy’s V-103 in Atlanta.

Picked by Dom Kennedy
Picked by Dom Kennedy

It Was a Good Day

Artist: 

Ice Cube

Album: 

The Predator

Year: 

1992

The beauty of the song — in which Ice Cube depicts a rare day in the ’hood in which everything breaks his way — is in its clarity, Dom Kennedy says. “Great storytelling. Easy for me to remember, and captivating,” he said. “It’s not stuff that has to grow on you: The first time you heard it, it’s like, ‘Yeah, that’s it right there.’ … These are the types of songs that are unforgettable in the rap genre.”

Kennedy also picked “Around the Way Girl” by LL Cool J.

Born, raised and still living in Los Angeles, Dom Kennedy represents a new wave of West Coast hip-hop. His 2010 mixtape, “From the Westside With Love,” catapulted him to popularity.

Picked by P-Lo
Picked by P-Lo

Blow the Whistle

Artist: 

Too $hort

Album: 

Blow the Whistle

Year: 

2006

“It’s so representative of the Bay,” P-Lo says. “You can go anywhere, and you can drop ‘Blow the Whistle,’ and it’s just going to be a great time.” P-Lo also feels strongly about “Burn Rubber,” another song by Too $hort: “I always say, like, when it’s my time to go, I would want my casket to be dropped to ‘Burn Rubber.’”

P-Lo, a 32-year-old Bay Area rapper, rose to popularity through collaborations with West Coast artists such as Kool John, E-40, YG and Kehlani.

Picked by Ludacris & Layzie Bone
Picked by Ludacris
Picked by Layzie Bone

I’m Bad

Artist: 

LL Cool J

Album: 

Bigger and Deffer

Year: 

1987

Ludacris credits the song — featuring LL’s bold and forcefully delivered braggadocio — with inspiring him. “I was in fourth grade and I knew every word of that record,” he says. “So that’s what defines hip-hop for me. It made me want to do what I’m doing, and if it weren’t for that record, I can’t say I’ll be where I’m at.”

“Remember when Michael Jackson came out with ‘Bad’ and it was a big thing for pop artists?” Layzie Bone asks. “LL Cool J had the wherewithal to do it as a rapper. He helped put rap on the map.”

Ludacris, a onetime Atlanta radio intern, became a mainstay on the early-2000s airwaves by mixing humor and charismatic delivery. Songs such as “Southern Hospitality” and “Stand Up” showcased talent he later used acting in the Fast & Furious franchise.

Layzie Bone is one of the five members of Bone Thugs-N-Harmony, considered one of hip-hop’s most melodic groups. The Cleveland group won a Grammy in 1997 for “Tha Crossroads,” their tribute to mentor Eazy-E, who died in 1995.

Picked by Royce da 5’9”
Picked by Royce da 5’9”

Can’t Tell Me Nothing

Artist: 

Kanye West

Album: 

Graduation

Year: 

2007

“It’s just a perfect song, man,” Royce says. “I used to subscribe to, like, things had to be super lyrical … everything used to be about artistic technique. And then I started to learn there is such a thing as something just feeling right. … ‘Can’t Tell Me Nothing,’ I just want to play it over and over again. I can’t listen to that [song] one time. If it comes on, I got to play it again at least twice, you know?” I feel like some [stuff] is classic like that. You’re not supposed to be able to explain it. ... I mean, it’s lightning in a bottle.”

Royce da 5′9″ is a Detroit MC known for his complex lyricism and projects with Eminem, DJ Premier and the supergroup Slaughterhouse.

Picked by Dante Ross
Picked by Dante Ross

They Reminisce Over You (T.R.O.Y.)

Artist: 

Pete Rock & CL Smooth

Album: 

Mecca and the Soul Brother

Year: 

1992

CL Smooth’s ode to family and his recently deceased friend Trouble T Roy works perfectly over Pete Rock’s evocative use of jazz samples and hip-hop drums. Dante Ross, the legendary A&R man and producer, reflects on both that song and a 1991 track by Gang Starr.

“Certainly ‘Just to Get a Rep’ by Gang Starr, something about the Jean-Jacques Perrey sample was so soulful and emotional, and rap to me didn’t necessarily have that feel to it at that point,” Ross says. “It was few and far between. It had a soul to it. It was almost like a blues record to me. I felt an emotion from it. The way Guru was rapping, it was an emotional record. Cerebral and emotional. Another version of that same kind of canon was ‘They Reminisce Over You (T.R.O.Y.)’ by Pete Rock and CL Smooth, which completely blew me away when I heard it. It was so emotive and beautiful. … They are beautiful pieces of art, to me.”

Dante Ross also picked Cypress Hill’s “How I Could Just Kill a Man.”

Dante Ross, who says his “talent was spotting talent,” began as the Beastie Boys’ messenger at Def Jam and lasted long enough as an A&R rep to write a book, “Son of the City.” In between, he helped steer Busta Rhymes, ODB and MF Doom and helped produce for Brand Nubian, Everlast and Carlos Santana.

Picked by Daddy-O of Stetsasonic
Picked by Daddy-O of Stetsasonic

Murder

Artist: 

UGK

Album: 

Ridin’ Dirty

Year: 

1996

Daddy-O insists he prefers collective works to single songs, and the Port Arthur, Tex., duo’s third album “Ridin’ Dirty” does it for him. “That’s my favorite album ever, and Pimp C is my favorite MC,” Daddy-O said. “It’s ‘The Message’ on crack.” Whereas Melle Mel’s rhymes on the 1982 song are considered the prime example of hip-hop’s potential to be more than just party music, UGK’s work is an even deeper expedition into a gritty world. Pimp C’s production and Texas drawl and Bun B’s flow on “Murder” — which Daddy-O calls “unparalleled” — helped open ears across the hip-hop spectrum to a sound they’d grow to love.

Daddy-O is the most well-known MC in the hip-hop band Stetsasonic, which also spawned renowned producer Prince Paul.

Picked by DJ Slugo
Picked by DJ Slugo

Self Destruction

Artist: 

The Stop the Violence Movement

Album: 

n/a

Year: 

1989

Boogie Down Productions, Stetsasonic, Kool Moe Dee, MC Lyte, Doug E. Fresh, Just-Ice, Heavy D and Public Enemy teamed up as the Stop The Violence Movement for a “We Are the World”-style anthem disassociating hip-hop and violence.

“That record right there? Changed it for me,” DJ Slugo said. “I was like, ‘Oooh, that’s deep.’ At that particular time, people were blaming hip-hop for a lot of the violence. And for me, they were telling the story of the poverty in the neighborhood and the structural things they felt like the government was doing to the neighborhoods — bringing crack in — and I just liked the storytelling of the record. It ain’t just hip-hop; America itself is doing the self-destruction. It makes you think, what was the issue before hip-hop? That violence existed before hip-hop.”

DJ Slugo also picked “Stop the Violence” by Boogie Down Productions.

DJ Slugo is a Chicago-based pioneer of “ghetto house” and juke music known for his DJing, production and remixing work.

Picked by Jeff Chang
Picked by Jeff Chang

I Am I Be

Artist: 

De La Soul

Album: 

Buhloone Mindstate

Year: 

1993

The album “didn’t have any big hits on it, but it’s the song I have to hear at least once a month. When I first heard it, it’s the song that made me think: ‘I can grow old to this. I can grow old with hip-hop,’” Chang says. “It really moved me. It’s about generations, it’s about community, it’s about family. It’s them telling their stories.

“It’s set to this music that, every time I hear it, I get really choked up, because I think about my family, my kids, and I think about people that have passed. The generations that are still coming, I want them to hear this song.”

Chang also picked “I Know You Got Soul” by Eric B. and Rakim.

Jeff Chang, a hip-hop historian and journalist, co-founded the independent label SoleSides (later Quannum Projects), which helped launch the careers of Blackalicious, DJ Shadow and Lyrics Born. He is the author of “Can’t Stop Won’t Stop.”

Picked by DJ Drama
Picked by DJ Drama

Juicy

Artist: 

The Notorious B.I.G.

Album: 

Ready to Die

Year: 

1994

“I just think it embodies everything about hip-hop,” DJ Drama says of Biggie’s “Juicy.” “He’s one of the greatest artists of all time. Sonically [and] lyrically, the way he tells his story just kind of like a started-from-the-bottom story and making it within the business.”

Adds Dante Ross: “He’s selling this, like, aspirational thing. But we talk about the soulfulness of hip-hop, and the emotion. You hear the emotion in what he’s talking about. Like you know, his aspirational wants and dreams, in a very kind of pop-friendly format. I thought that was genius.”

“Biggie has been my favorite: just pure rap, pure rhyming,” Dom Kennedy says. “He made it effortless to understand and to hear what he was saying.”

DJ Drama also chose “Jackin’ for Beats” by Ice Cube.

Known as the “King of the Mixtape,” DJ Drama was the mind behind the early-2000s Gangsta Grillz mixtapes that spread Southern hip-hop. His new podcast, “DJ Drama’s Gangsta Grillz Podcast,” delves in further.

Picked by Doug E. Fresh
Picked by Doug E. Fresh

Superrappin’

Artist: 

Grandmaster Flash & the Furious Five

Album: 

n/a

Year: 

1979

“Because it’s the breakdown of the science of hip-hop,” Doug E. Fresh says when explaining this choice. “The skill level is unbelievable. The flows are unbelievable. Grandmaster Flash & the Furious Five are the foundation of it, and I think it’s the most incredible pass-of-the-mic style, which was the original style in hip-hop. And it’s the best that I’ve ever heard. Grandmaster Flash & the Furious Five is one of the best to ever do this.”

Doug E. Fresh’s rapping and beatboxing alongside the Get Fresh Crew earned him the title of “The World’s Greatest Entertainer” and helped introduce the world to another hip-hop great — Slick Rick.

Picked by Mannie Fresh
Picked by Mannie Fresh

Bass Machine

Artist: 

T La Rock

Album: 

Lyrical King (From the Boogie Down Bronx)

Year: 

1987

Mannie Fresh says that the triplets and drumrolls from the Kurtis Mantronik production hooked him, but it was the New Yorkers’ new use of the Roland TR-808 Rhythm Composer drum machine that blew him away. “He turned it into an instrument. … Now, [there are] so many people that’s doing that, turning the 808s up, the bass lines and all of that. He did that way, way back before it was even thought about.”

The son of a DJ in New Orleans, Mannie Fresh has produced or rapped on some of the city’s most important hip-hop hits as part of Cash Money Records.

Picked by The Alchemist
Picked by The Alchemist

Keep It Rollin’

Artist: 

A Tribe Called Quest featuring Large Professor

Album: 

Midnight Marauders

Year: 

1993

Large Professor produced A Tribe Called Quest’s “Keep it Rollin’,” and the Alchemist considers the track a “blueprint” for his own style. “The way the beat was made, and just the style and selection of samples that Large Professor used, where it sat on the album, him as a producer also rapping on a song and killing it on the third verse,” the Alchemist says. “It had a lot of effect on how I approached producing and also rap, and being able to do both.”

One of hip-hop’s most consistent producers, the Alchemist has provided soundscapes for Mobb Deep, Jadakiss, Dilated Peoples, Action Bronson and Freddie Gibbs. He performs alongside Evidence as Step Brothers.

Picked by Vic Mensa
Picked by Vic Mensa

I Ain’t Mad at Cha

Artist: 

2Pac

Album: 

All Eyez on Me

Year: 

1996

“‘I Ain’t Mad at Cha’ is a quintessential Black American story of change. And just life,” Mensa says. “He illustrates through these different perspectives of the story the relationship between Black men and incarceration, and relationships between Black men and Black women. And approaches the gigantic topic of change, you know, with just such confidence, nuance and relaxation.”

Mensa also picked 2Pac’s “Me Against the World.”

Vic Mensa, an outspoken Chicago MC, buzzed throughout the 2010s on mixtapes, EPs and albums alongside artists as varied as Ye, Skrillex and Pharrell Williams. He’s the founder of the hip-hop collective Savemoney.

Picked by Remy Ma
Picked by Remy Ma

Oh No

Artist: 

Lil Wayne

Album: 

Tha Carter II

Year: 

2005

“The beat is crazy. The way he was rapping, he was in pocket,” she remembers. “The way people normally rap and the way they normally end it, he was more so talking, saying whatever comes, and it just sounded fire. There was no hook. It was just him rapping beginning to end. The beat is really simple, but still hard and dramatic.”

Remy Ma emerged in the early 2000s as a Big Pun protégée and earned Grammy nominations for “All the Way Up” and “Lean Back.” She starred on TV’s “Love & Hip Hop” alongside husband Papoose and battled top female MCs.

Picked by Lil’ Flip
Picked by Lil’ Flip

Ebonics

Artist: 

Big L

Album: 

The Big Picture

Year: 

2000

The song, through Big L’s trademark cleverness, explains a variety of hip-hop slang from the late ’90s. Flip loves hearing all the terms in “Ebonics,” which makes sense for a rapper who took the melting pot that is Houston and expressed that in his career by working with people from all rap fiefdoms. The group the Girll Codee remade “Ebonics” in 2021 with updated slang and explanations.

Lil’ Flip also picked “Anotha Day in tha Hood” by 8Ball & MJG.

Known for his singles “Game Over (Flip)” and “Sunshine,” Lil’ Flip has told stories of Houston over often lighthearted beats.

Picked by Big Daddy Kane
Picked by Big Daddy Kane

Go Stetsa I

Artist: 

Stetsasonic

Album: 

On Fire

Year: 

1986

“It was that Brooklyn anthem. You would see cats in the Latin Quarter lose their minds. You would see the ‘grimies’ … it would trigger something in them where they had to snatch chains. It just brought out that adrenaline, right from the opening drumroll.”

Big Daddy Kane introduced complex lyricism, showmanship and the idea that rappers could be sex symbols while reigning with the Juice Crew in the late ’80s.

Picked by Parrish Smith of EPMD
Picked by Parrish Smith of EPMD

Rock Box

Artist: 

Run-DMC

Album: 

Run-DMC

Year: 

1983

Run-DMC and Jam Master Jay “kicked the door open for everybody,” former “Yo! MTV Raps” host Ed Lover said, noting their ascent from “King of Rock” to “Raising Hell” to “Tougher Than Leather.” But it’s a song from the group’s 1983 debut album, with its boom-bap drums, guitar riff and crisp rhymes, that stood out as Parrish Smith ran through a list of memorable hip-hop classics. “I don’t think people talk about Run enough. … When you talk about what an MC is, the master of ceremonies, the person who controls the crowd, you have to mention Run,” says DoItAll of Lords of the Underground.

Half of the group EPMD, and part of the Hit Squad, which spawned the careers of Redman, K-Solo and Das EFX, Parrish “PMD” Smith was known for his slow flow.

Picked by DoItAll of Lords of the Underground
Picked by DoItAll of Lords of the Underground

Top Billin’

Artist: 

Audio Two

Album: 

What More Can I Say?

Year: 

1987

DoItAll showed love for a handful of classic artists but says the party-rocking drums, “Go Brooklyn” chant and sharp lyrics from Audio Two’s Milk Dee gave him a feeling he could not deny.

“The Audio Two, whenever I hear that, those drums, I think that’s probably one of the illest breaks in hip-hop,” he says. “‘Milk is chillin’, Giz is chillin’’ … who doesn’t know that?”

DoItAll burst onto the scene in 1993 with Lords of the Underground, with hits “Funky Child,” “Chief Rocka” and “Tic Toc.” He then returned to Newark to become a West Ward councilman.

Picked by Z-Ro
Picked by Z-Ro

I Tried

Artist: 

Geto Boys

Album: 

The Foundation

Year: 

2005

“There’s so many people out here who give their best and they feel as if they didn’t make it, they didn’t achieve their goal — but they tried,” Z-Ro says of Geto Boys, adding that he isn’t immune to that feeling despite being a Houston rap legend. He said he has “probably a little more than the regular independent artist,” but he isn’t famous. “People praise me like I’m Bon Jovi or something,” he said. Later on, when talking about trying and failing, he said, “It kind of angers me because I know I’m supposed to be so much farther than where I am.”

Regarded as one of Houston’s most underrated rappers, Z-Ro has been a pillar in the city’s hip-hop scene for decades with brutally honest lyrics.

Picked by DJ Kool
Picked by DJ Kool

Welcome to the Terrordome

Artist: 

Public Enemy

Album: 

Fear of a Black Planet

Year: 

1990

Public Enemy weaved its politically charged, pro-Black messages over production featuring a smorgasbord of sounds that matched the urgency of the MCs. “I’m a huge Public Enemy fan,” DJ Kool said. “I feel some type of way [about] Chuck and Flavor. … Anybody that knows anything about hip-hop knows [this song] takes you up here and back. It takes you through the roof with the Bomb Squad production. Lights out.”

DJ Kool describes himself as half hip-hop and half go-go. His 1996 hit “Let Me Clear My Throat” tears the club up to this day.

Picked by Tobe Nwigwe
Picked by Tobe Nwigwe

Regulate

Artist: 

Warren G featuring Nate Dogg

Album: 

Regulate … G Funk Era

Year: 

1994

“That’s the first song I learned,” Tobe Nwigwe said during the Essence Festival in New Orleans in July.

“That’s mine,” his wife, Martica, who was sitting next to him on the white couch in the press room, said immediately after.

“Oh, for real, that’s your favorite song too?” he said to her. “That’s the first song everybody learned. It was that good.”

Houston rapper Tobe Nwigwe embraces family and fatherhood and regularly performs with his wife and kids by his side. He was nominated for best new artist at the 2023 Grammy Awards.

Picked by Posdnuos of De La Soul
Picked by Posdnuos of De La Soul

Criminal Minded

Artist: 

Boogie Down Productions

Album: 

Criminal Minded

Year: 

1987

This song transports Posdnuos back in time. “In that period of my life, I was still going to the Latin Quarter to see [KRS-One] perform,” he says. “This is before we were on, before we were even signed. It means so much to me because I can see him doing it live, and it was one of those songs when it came out, you could play it over and over again. He had so much confidence. It was him going up against the Juice Crew, and it showed so much of his style.”

Also known as Plug 1, Posdnuos is a founding member of De La Soul, one of the “Native Tongues” groups that helped stretch hip-hop’s boundaries and shifted how Blackness was viewed. De La Soul’s lyrics were intelligent, fun-loving and weird.

Picked by Roxanne Shante
Picked by Roxanne Shante

Adventures of Super Rhyme (Rap)

Artist: 

Jimmy Spicer

Album: 

Adventures of Super Rhyme

Year: 

1980

Spicer raps for more than 15 minutes with no chorus or hook, breaking into a Dracula voice midway through, and recounting a story as Aladdin talking to his genie. “When I heard that,” Shante says, “I wanted to rhyme as long as he could, without having it written. And I knew I could.”

Roxanne Shante, one of hip-hop’s first female stars as part of the Juice Crew, is known for her freestyle skills and for inspiring Nas. She hosts a drive-time show on SiriusXM’s Rock The Bells.

Picked by Kamaiyah
Picked by Kamaiyah

Hot Boyz (Remix)

Artist: 

Missy Elliott featuring Nas, Eve and Q-Tip

Album: 

Da Real World

Year: 

1999

“The ‘Hot Boyz’ remix, with Eve and Nas, that’s a vivid memory for me,” Kamaiyah said. “That video is crazy. That’s when she started to transcend into pop culture, in my opinion. That was one of those records where Missy let people know, ‘Don’t … play with me.’ I just remember that summer. It was just like all over the radio, and I was like, ‘Damn, she steppin’.’”

Kamaiyah also picked “So Many Tears” and “Baby Don’t Cry” by 2Pac.

Oakland, Calif.-raised Kamaiyah released her debut mixtape, “A Good Night in the Ghetto,” in 2016, cementing her status as a promising young artist in the Bay Area hip-hop scene.

Picked by Phonte of Little Brother
Picked by Phonte of Little Brother

We Can’t Be Stopped

Artist: 

Geto Boys

Album: 

We Can’t Be Stopped

Year: 

1991

Phonte, a Greensboro, N.C., native, points to Willie D’s bars at the end of the song — which starts off with a reaction to Geffen Records refusing to work with Geto Boys but pushing Guns N’ Roses — as an example of how territorial rap can be:

We’re from the ... South / Now what was this ... about/ That we had to be from Cali or New York/ Anybody can make it that got heart.

“It was a call to action,” Phonte says. “… So hearing Willie D, hearing Geto Boys’ ‘We Can’t Be Stopped,’ him saying that line … really spoke to me, and it was like, ‘Yeah, it don’t matter where you from, you know, saying if you got the heart to do this, you can band against [people] from anywhere.’ And that was something that always resonated with me.”

Phonte also picked “Lost at Birth” by Public Enemy.

Phonte is a standout MC and singer from the seminal North Carolina group Little Brother, and half of the Foreign Exchange. He is a sought-after soloist for his clever guest bars, and Drake lists him as an influence.

Picked by Scarface
Picked by Scarface

Youthful Expression

Artist: 

A Tribe Called Quest

Album: 

People’s Instinctive Travels and the Paths of Rhythm

Year: 

1990

Tribe went on to put out more well-known hits such as “Electric Relaxation,” “Check the Rhime” and “Award Tour,” but Scarface went out on a limb with this song from the group’s debut album. Asked why he loved the song, Scarface simply responded: “That motherf---er’s jamming. … That’s how they do.”

A member of the seminal Houston hip-hop group Geto Boys, Scarface is often heralded as one of the finest MCs that Texas has produced.

Picked by E-40
Picked by E-40

Dope Fiend Beat

Artist: 

Too $hort

Album: 

Born to Mack

Year: 

1987

“I’m talking the streets, you feel me? Hip-hop is urban. So if you’re from an urban community, it’s easy for you to relate to it, you know what I mean?” E-40 asks. “And that’s me, raised in an urban community. ‘Dope Fiend Beat,’ I was raised around dope fiends. I’m raised around D-boys [dealers]. That’s my memories.”

A staple in Bay Area hip-hop, E-40 is known for his inventive use of slang and tongue-twisting wordplay. He founded Sick Wid’ It Records and is part of supergroup Mount Westmore with Too $hort, Ice Cube and Snoop Dogg.

Picked by DJ Paul of Three 6 Mafia
Picked by DJ Paul of Three 6 Mafia

A Touch of Jazz

Artist: 

DJ Jazzy Jeff & the Fresh Prince

Album: 

Rock the House

Year: 

1987

While many of the artists on this list are MCs, there would be no hip-hop without DJs to create, play and blend the music. And DJ Paul points to Jazzy Jeff as one of the best ever to mix tracks. “It was such a dope blend,” he says of “A Touch of Jazz.”

DJ Paul provided the bewitching beats for Three 6 Mafia’s swell of success, which crested in 2006 when they won an Oscar for best original song for “It’s Hard out Here for a Pimp.”

Picked by Trina
Picked by Trina

Crazy in Love

Artist: 

Beyoncé featuring Jay-Z

Album: 

Dangerously in Love

Year: 

2003

MCs once shunned R&B collaborations for fear it would make them look soft, while R&B artists would make two versions of a song: one with a rap midway through, and a radio-safe version without the rap. By the time Beyoncé and Jay-Z made “Crazy in Love,” a horn-fueled, undeniable party rocker, there were no such unwritten rules. “Everything Beyoncé, that’s my whole inspiration for my music, to be honest,” Trina said.

Southern rap superstar Trina helped lay the foundation for today’s biggest female hip-hop artists. First featured on Trick Daddy’s album, the Miami native quickly found fame with hits such as “Da Baddest B----,” “Here We Go” and “Single Again.”

Picked by Dear Silas
Picked by Dear Silas

Spread

Artist: 

OutKast

Album: 

Speakerboxxx/The Love Below

Year: 

2003

Big Boi and André 3000 achieved legendary status with their first four albums. OutKast’s fifth release, the double album “Speakerboxxx/The Love Below,” spawned huge hits in “Hey Ya!” and “The Way You Move.” But Dear Silas picked a song from André 3000’s “The Love Below” that he says has a classic appeal. “It could be made today and nobody would blink,” Dear Silas says of “Spread.”

Dear Silas also picked “Roses” by Kanye West, now known as Ye.

A trained trumpeter, Dear Silas, a native of Jackson, Miss., created the viral song “Skrr Skrr,” which has been streamed more than 5 million times on Spotify.

Picked by The Lady of Rage
Picked by The Lady of Rage

My Melody

Artist: 

Eric B. & Rakim

Album: 

Paid in Full

Year: 

1987

Several artists The Post spoke to brought up Rakim’s influence on hip-hop, as he helped carve space for lyrics delivered in a smooth and forceful monotone instead of upbeat party rhymes. But when this song popped into the Lady of Rage’s mind, it was the beat that she couldn’t help but hum.

The Lady of Rage also picked “The Theme (It’s Party Time)” by Tracey Lee.

Known for her signature two-Afro-puff hairstyle, the Lady of Rage redefined what it meant to be a woman in hip-hop while rapping alongside Dr. Dre and Snoop Dogg on Death Row Records.

Picked by Jermaine Dupri
Picked by Jermaine Dupri

You’re a Customer

Artist: 

EPMD

Album: 

Strictly Business

Year: 

1988

“This really was one that pierced my ears for a long time. And I couldn’t get away from it, it was like almost infectious,” Jermaine Dupri remembers. … And the way that EPMD rapped back and forth with each other, I basically mimicked with me and Brat. I wanted to do it differently, so it sounds like a girl and a guy, but I got that style from EPMD.”

Dante Ross also mentioned this song, “because it was like, ‘Oh, there’s two Rakims in this group.’ That was my initial thought because they both had the monotone thing going on, like Rakim did. And it was just so, so cool.”

Jermaine Dupri started out dancing for Whodini and grew into one of hip-hop’s heavyweight producers, discovering Kris Kross and starting So So Def Recordings with artists such as Da Brat and the R&B group Xscape.

Picked by Kid Capri
Picked by Kid Capri

Empire State of Mind

Artist: 

Jay-Z featuring Alicia Keys

Album: 

The Blueprint 3

Year: 

2009

“I think when I hear Jay-Z’s New York record, I think that gives a sense of pride; it’s almost like you’re hearing ‘New York, New York’ by Frank Sinatra again,” Kid Capri says. “‘Empire State’ is one of those records that when you hear it … you ain’t even got to live in New York. I play that record in places like Kentucky, places like Omaha, Nebraska, and watch these people act like they’re in New York by the way they receive it. It’s a prideful record.”

Kid Capri also picked “The Bridge Is Over” by Boogie Down Productions.

Kid Capri is considered one of hip-hop’s all-time great DJs for his live turntable work, sought-after mixtapes and production for Heavy D, Nas and Big L. He was the in-house DJ for HBO’s “Def Comedy Jam” and is a host on SiriusXM’s Fly channel.

About this story

Reporters

Keith McMillan, Amber Ferguson, Anumita Kaur, Ben Brasch, Kim Bellware, Timothy Bella, Sean Carter

Editors

Keith McMillan, Steven Johnson

Designers

María Alconada Brooks, Shikha Subramaniam, Aadit Tambe

Developer

Aadit Tambe

Design Editors

Eddie Alvarez, Matt Callahan

Photo Editor

Maya Valentine

Copy Editors

Mike Cirelli, Shay Quillen, Timothy Bella

Illustration by

David Milan for The Washington Post

Editor’s note: The chosen versions of “Hot Boyz” and “Self Destruction” were not available on Spotify at the time of publication.