50 essential hip-hop songs to celebrate 50 years: Grandmaster Flash, Jay-Z, Outkast, more

“Rapper’s Delight” will always be considered the song that introduced hip-hop to the masses.

The Sugarhill Gang classic with its tongue-twisting opening – “I said a-hip, hop, the hippie, the hippie to the hip hip hop-a you don’t stop the rock” – and heartbeat bass line was a novelty in 1979 and deserves its standing as one of the most sampled and revered in the then-burgeoning genre.

Since then, hip-hop has spawned a mass of subgenres - gangsta rap, crunk and trap among them.

Hundreds of hip-hop songs deserve recognition for their meaning and their beats. But for now, in random order, are 50 essential hip-hop tracks to celebrate five decades of groundbreaking music.

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50. Goodie Mob, ‘Cell Therapy’ (1995)

The lead single from their “Soul Food” debut album spotlights Cee Lo Green’s soulful voice as he sing-raps verses between a sticky, stalking chorus. The song also introduced Organized Noize, the Atlanta production crew of Rico Wade, Ray Murray and Sleepy Brown, who would become integral to Outkast’s catalog.

49. 2 Live Crew, ‘Me So Horny’ (1989)

The Top 20 hit for the Miami group spearheaded by Luther Campbell (aka Uncle Luke) is a dopey ode to sex that gets raunchier as it progresses. However its legacy isn’t musical, but legal. It’s almost amusing to remember a time when a lewd song and album (“As Nasty As They Wanna Be”) was so shocking, it prompted a Florida judge to declare 2 Live Crew’s work obscene.

48. Eminem, ‘My Name Is’ (1999)

Between its staccato beat and Eminem’s humorous storytelling that namechecked pop culture touchstones of the time (Spice Girls, Nine Inch Nails, Dr. Dre, Pamela Lee), the lead single from the Detroit breakout’s sophomore album (“The Slim Shady LP”) is an appetizer of what he would soon produce. Chka-chka Slim Shady forever.

47. Doug E. Fresh and Slick Rick, ‘La Di Da Di’ (1985)

Old-school beatboxing from Doug E. Fresh coupled with Slick Rick’s nasal delivery of mundane preparation for a date set the scene as Rick promises, “we don’t cause trouble, we don’t bother nobody.” The lackadaisical cadence is testament to the early days of rap, when storytelling trumped tempo. The hip-hop classic has been referenced in song by artists ranging from Robbie Williams to Color Me Badd.

46.  Migos (featuring Lil Uzi Vert), ‘Bad and Boujee’ (2016)

“Raindrop, drop top” spawned a gazillion memes and earned the Atlanta trio of Quavo, Offset and Takeoff their first No. 1 on the Billboard Hot 100. The song misses the contributions of Takeoff, omitted due to “timing,” but the snappy trap track is an attention-grabbing precursor to follow-up hits “Walk It Talk It,” “Stir Fry” and “T-Shirt.” (Takeoff was shot and killed in November 2022.)

45. Public Enemy, ‘Fight the Power’ (1989)

The bluntness of Public Enemy could never be curbed, and the defiant anthem commissioned by Spike Lee for “Do the Right Thing” has been solidified as one of the most important statements in hip-hop history: “Our freedom of speech is freedom or death/We got to fight the powers that be.”

44. Three 6 Mafia, ‘Hard Out Here for a Pimp’ (2005)

Probably no one was more surprised than the Memphis collective themselves when the group’s name was called as the best original song Oscar winner in 2006 for their performance on the “Hustle & Flow” soundtrack. The combination of a catchy song with a repetitive, radio-friendly chorus and invaluable exposure saw the group applauded after a decade of work.

43. Outkast, ‘Player's Ball’ (1993)

André 3000 wasn’t kidding when he proclaimed, “The South got something to say” at the 1995 Source Awards. The Atlanta duo that also includes Big Boi might have busted down the mainstream door and scored Grammy love in 2004 for “Hey Ya.” But it’s more important to remember their debut gem, with its swishy soul chorus and lyrical proof that the prophets of the South had arrived.

42. Grandmaster Flash and the Furious Five, ‘The Message’ (1982)

Squiggly synthesizers and a loping beat anchor the title track of the debut album from the Bronx, New York, sextet. But it’s the political and social commentary that made the song a pioneer of its time and laid the foundation for socially conscious hip-hop.

41. LL Cool J, ‘Mama Said Knock You Out’ (1990)

“Don’t call it a comeback?” Actually, we will, considering the deflated state of Ladies Love Cool James’ career at the time. But the thick bass-and-drum thump and LL’s potent delivery proved the winning touch to reestablish his dominance.

40. Kurtis Blow, ‘The Breaks’ (1980)

A slinky funk breakdown less than a minute into the rap classic still pops out, as does the clean guitar jangle that powers the song. Blow, a native New Yorker, hit a milestone with the track: It was the first rap song certified gold (500,000 copies sold).

39. Missy Elliott, ‘Get UR Freak On’ (2001)

With producer Timbaland, a fellow Virginian, behind the board, Elliott dropped a wholly original jam. When was the last time the native music of Punjab – bhangra – was heard in a rap song? That stabbing rhythm coupled with Elliott’s funny and fierce commands landed her in the Top 10 of the Billboard Hot 100.

38. Kanye West, ‘Jesus Walks’ (2004)

An argument could be made that West’s vast catalog holds bigger hits - “Gold Digger,” with that priceless assist from Jamie Foxx, or “Stronger,” with the inventive electro-elements from Daft Punk, for sure. But this early hit from his debut (“The College Dropout”) that mixes gospel, a marching band and lyrics probing spirituality indicated there was something unique about West. 

37. Salt-N-Pepa, ‘Push It’ (1987)

The Queens group of Cheryl “Salt” James and Sandra “Pepa” Denton (along with Spinderella, aka Deidra Roper), found a niche in the late-‘80s with a grinding thumper that wasn’t even initially a single (it was the B-side to “Tramp”). But it identified a sound that would reappear in their other timeless pop-rap hits “Let’s Talk About Sex” and “Shoop.”

36. Lil Kim, ‘No Time’ (1996)

The tough-talking Brooklyn-born freestyle expert discovered by Notorious B.I.G.  established herself as a sexually dominant persona spitting out hardcore rap on her debut single featuring Puff Daddy. But the Queen Bee could also play with the popsters for a remake of “Lady Marmalade,” as she did in 2001 with Christina Aguilera, Mya and Pink.

35. Coolio, ‘Gangsta’s Paradise’ (1995)

Given his penchant for lighthearted, bouncy material (“Fantastic Voyage”), the dramatic intonations of this megahit were both surprising and appealing. Coolio, who died in 2022, netted the biggest-selling single of 1995, according to Billboard, and snagged a best rap solo performance Grammy for the creeping song, which borrows heavily from Stevie Wonder’s 1976 album track, “Pastime Paradise.”

34. Fugees, ‘Ready or Not’ (1996)

Wyclef Jean, Lauryn Hill and Pras Michel only released two albums, but their second (“The Score”) remains a hip-hop benchmark. Yes, their remake of Roberta Flack’s “Killing Me Softly with His Song” is their greatest tie to the masses, but the sing-songy “Ready or Not,” with its delectable Delfonics sample - “Ready or Not Here I Come (Can’t Hide from Love”) - spotlights the trio’s joint harmony.

33. Nas featuring Puff Daddy, ‘Hate Me Now’ (1999)

A diatribe about jealousy meshed with a snapping snare wasn’t as big of a hit as “Street Dreams” or “Got Ur Self A …,” but the genuine defiance in Nas’ rhymes lingers long after listening.

32. Kendrick Lamar, ‘Alright’ (2015)

It’s a challenge to pluck one song from the young catalog of a Pulitzer Prize (in music) winner. Lamar’s depth is bottomless, but this “To Pimp a Butterfly” offering, with background vocals from co-producer Pharrell, a zigzagging rhythm and lyrics such as “Tell ‘em all to come and get me/reapin’ everything I sow/so my karma come in heaven/no preliminary hearings on my record,” is but a glimpse at his genius.

31. Jay-Z, ‘Hard Knock Life (Ghetto Anthem)’ (1998)

The idea of using a show tune (“Hard Knock Life,” from “Annie”) in a blistering rap track was not only novel, but ridiculously clever. Jay-Z is an undisputed king of the genre and his ability to spin a tale about poverty and death interspersed with a kid’s chorus piqued the attention of the mainstream and jumpstarted his career to superstardom.

30. Snoop Dogg, ‘Who Am I (What’s My Name?)’ (1993)

If you know nothing else about the businessman-game-show-host-friend-of-Martha-Stewart, you know “Bow wow wow, yippie-yo-yippie-yay,” the indelible hook that introduced the rapper then known as Snoop Doggy Dogg. His languid flow coupled with obvious musical influences of George Clinton (“Atomic Dog”) and Parliament’s “Give Up the Funk (Tear the Roof Off the Sucker)” merged for a chill confection.

29. Nicki Minaj, ‘Super Bass’ (2011)

The Trinidadian wordsmith landed with an electronic-fueled pop-hip-hop jam highlighted by her fun delivery. The melodic chorus – sung by Ester Dean – underscored how Minaj, now a 100 million-plus record seller, had tapped into an appealing formula.

28. Bone Thugs-N-Harmony, ‘Tha Crossroads’ (1996)

Rooted in sorrow, the song dedicated to the group’s mentor, Eazy-E, glides and finger snaps as the Cleveland quintet praises God while ruminating on the passage of time. Their No. 1 hit also won a Grammy (best rap performance by a duo or group) in 1997.

27. Mos Def, ‘Ms. Fat Booty’ (1999)

Perhaps not the most politically correct title, the Aretha Franklin-sampling song (“One Step Ahead”) served as an intriguing introduction to the Brooklyn rapper known as Yasiin Bey since retiring his Mos Def moniker in late 2011. A liquid flow and vivid lyrics about flirting with a girl at a club (“She spot me like paparazzi/shot me a glance in that Catwoman stance”) instantly captivate.

26. Dr. Dre featuring Snoop Doggy Dogg, ‘Nuthin’ But a ‘G’ Thang’ (1993)

In time, he would be recognized as one of the mightiest producers in the game. But in the early ‘90s, Dre’s swinging beats and salacious lyrics – the song was considered a misogynistic headache by many – bumped him to the top of the charts.

25. A Tribe Called Quest, ‘Bonita Applebum’ (1990)

The New York quartet of Q-Tip, Phife Dawg, Jarobi White and Ali Shaheed Muhammad utilized repetition as the keystone of this languid head-nodder, a straight-up-sexy tease driven by jazz-inspired keyboard notes.

24. 50 Cent, ‘In da Club’ (2003)

It was the inescapable soundtrack at frat houses and strip clubs and the breakthrough smash for the rapper, who struggled for a few years prior to make headway in the industry (a 2002 meeting with Eminem helped). The shuffling beat and easy-to-mimic lyrics have kept this a favorite at sports venues and throwback club nights.

23. Run-D.M.C., ‘Sucker M.C.'s’ (1983)

The B-side to debut single “It’s Like That” cemented Run-D.M.C.’s presence with primitive electronic beats, minimal DJ scratching and the emphasis on flow, which would become a hallmark for the Queens trio of Joseph “Run” Simmons, Darryl “D.M.C.” McDaniels and the late Jason “Jam Master Jay” Mizell.

22. Beastie Boys, ‘Sabotage’ (1994)

Sure, “(You Gotta) Fight For Your Right (To Party)” remains a karaoke staple thanks to its juvenile fist-pumping sentiment and screeching chorus. But this blazer better exemplified the Beasties’ fusion of punk rock and rap with its thundering drums and buzzing bass line.

21. N.W.A. ‘Straight Outta Compton’ (1988)

The lead single from their debut album of the same name, this bracing burst of adrenaline defined West Coast rap of the era. With the inclusion of Ice Cube, Eazy-E, MC Ren and Dr. Dre, N.W.A. is heralded as one of the most influential groups in hip-hop.

20. Cypress Hill, ‘Insane in the Brain’ (1993)

A springy beat and snippets of songs from James Brown and Sly and the Family Stone blended into a cauldron of chest-thumping bass and quirky sound effects. The result was a No. 1 rap hit, as well as a No. 19 appearance on the Billboard Hot 100.

19. The Roots with Raphael Saadiq, ‘What They Do’ (1996)

Ahmir “Questlove” Thompson and Tariq “Black Thought” Trotter took the soul of their native Philadelphia and the core of rap to brand a new form of hip-hop eclecticism. Their love of music of all genres is evident in the group’s chameleonic efforts, but truly gleams in this scholarly discourse about the meaning of hip-hop.

18. Cardi B, ‘Bodak Yellow’ (2018)

She told us from the outset that she makes “money moves” and there is never a question about the inherent shrewdness of the New York rapper born Belcalis Cephus. Her distinctive style and fierce attitude are evidenced on her slinky debut, which hit No. 1 on the Billboard Hot 100.

17. The Notorious B.I.G., ‘Hypnotize’ (1997)

One of the many songs to call back to “La Di Da Di,” this final single before Biggie Smalls’ death in a drive-by shooting coasts with a slithering thump while R&B singer Pamela Long provides the heart of the chorus. Its ascension to No. 1 on the Billboard Hot 100 made The Notorious B.I.G. the fifth artist – at the time – to top the chart posthumously.

16. Queen Latifah, ‘U.N.I.T.Y.’ (1993)

Who could listen to this well-crafted message and not proclaim, all hail the queen? With forthright lyrics condemning misogyny and domestic violence, Latifah unwraps her stalwart stance over a sneaky sax riff, her voice a hammer inside a velvet glove.

15. T.I., ‘Top Back’ (2006)

The Atlanta maestro leaned into swaying pop choruses with “Whatever You Like” and “Live Your Life” but this major production from his fourth album, “King,” brought his trap specialty to the mainstream.

14. Wu-Tang Clan, ‘Protect Ya Neck’ (1992)

The debut from the New York crew featuring eight of the original Wu-Tang members including Method Man, RZA and Ghostface Killah is a rugged romp that flourished as an independent, underground single that Wu-Tang shopped at hip-hop record stores around Staten Island. A record deal eventually arrived and the group’s legacy has been long secured.

13. Gucci Mane, ‘Lemonade’ (2009)

Along with T.I., Gucci is considered a founding father of trap music, born on the streets of Atlanta. This track from his sixth studio album, “The State Vs. Radric Davis,” is, on its surface, all about yellow things (cars, jewelry, carpeting). But it’s really about basking in success, which Gucci had well-earned.

12. Ice Cube, ‘It Was a Good Day’ (1993)

Sometimes a song really is about nothing more than basic happiness. Ice Cube rolls through a litany of things that have gone well – no barking dogs or carjackings, a call from a girl he likes, playing basketball with his homies. For an artist associated with gangsta raps and heavy themes, it’s a pleasant detour.

11. Busta Rhymes, ‘Break Ya Neck’ (2001)

With a snarl and smile, Busta announces he’s “back in town” before huffing through this muscular bumper. Drips of Red Hot Chili Peppers’ “Give it Away” and production from Dr. Dre take the song in a different direction after about a minute, but Busta’s trademark rapid-fire spitting is intact.

10. KRS-One, ‘My Philosophy’ (1988)

Throughout his career, the Bronx-raised rapper infused his music with the tenets of his moniker: Knowledge Reigns Supreme Over Nearly Everyone. Weaving spoken-word with rhymes, KRS-One and his Boogie Down Productions cohorts lean into their frustration with rappers who might have joined the game for the wrong reasons: “It ain’t about money ‘cause we all make dollars.”

9. Tupac Shakur, ‘Dear Mama’ (1995)

Considered one of the most substantial hip-hop tracks in history, the open-hearted slice of vulnerability details Shakur’s childhood of poverty, lack of a father figure and the struggles of his mother, Afeni, with drugs. It’s a tear-inducing tribute to the woman he calls “sweet lady,” made all the more poignant after Shakur’s death in a drive-by shooting a year after the song’s release.  

8. Lil Wayne, ‘A Milli’ (2008)

The youngster amid the Cash Money Records label when he was signed in 1995, Wayne injected a gummy New Orleans sound into his music, spotlighted on this 2009 Grammy winner (best rap solo performance) as he unleashes his flow over a brittle beat.

7. DMX, ‘Ruff Ryders Anthem’ (1998)

Produced by Swizz Beatz, who combined his New York hip-hop sensibilities with a beat he shaped in Atlanta, the gritty song fit the wheelhouse of the routinely robust work presented by DMX, who died in 2021. It also landed DMX his first platinum-selling single.

6. Future featuring Pharrell, Pusha T and Casino, 'Move That Dope' (2014)

Always sounding as if he doesn’t care if you’re listening or not, the Atlanta hitmaker integrated Auto-tune into a molasses trap beat as he pilots lyrics about drugs with a little help from Salt-N-Pepa’s “Push It.”

5. Lil Nas X, ‘Montero (Call Me By Your Name)’ (2021)

The inane “Old Town Road” catapulted the Atlanta native (legally known as Montero Hill) to pop culture saturation. But the lead single from his debut album is the song that matters, a brave exploration of homosexuality and gay romance that earned Lil Nas X some critics, but won the battle of authenticity.

4. Rick Ross, ‘Hustlin’’ (2006)

The music mogul became an instant success with his first single, which offered a catchphrase (“Every day I’m hustlin’”) couched among his slow-drip rhymes about being a drug-dealing kingpin. Ross has since released – or featured on – more than 145 singles, proving his boss-dom.

3. Drake, ‘Best I Ever Had’ (2009)

Some might not identify Drake as a rapper given his proclivity for coating his rhymes with supple R&B elements. His first No. 1 hit from his inaugural EP, “So Far Gone,” furthers that mindset given the song’s melodic bent, but it also hints at Drake’s musical intentions.

2. Ludacris, featuring Pharrell, ‘Money Maker’ (2006)

Walk into any Atlanta strip club and this anthem from one of the city’s most successful exports will be heard. Often. With the clipped beats and abrupt pulse characteristic of Williams and Chad Hugo – his producing partner in The Neptunes – the song floats on Ludacris’ reworking of the Elmore James blues classic, “Shake Your Moneymaker.”

1. Grandmaster Melle Mel and the Furious Five, ‘White Lines’ (1983)

Co-written by Melle Mel and Sylvia Robinson (founder of Sugar Hill Records), the ominous warning of the dangers of cocaine is revered for its insinuating bass line. The track is also remembered for the legal fracas that ensued because that bass line came from an uncredited Liquid Liquid song, “Cavern.” But the effect of “White Lines” lingers, notably in a muscular 1995 cover by Duran Duran that is a staple in the band’s live shows.

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