90s Rap Songs featuring Cypress Hill
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The Best Old School Hip Hop from the 80s and 90s

In an era defined by raw lyricism, gritty storytelling and sample-heavy beats, 90s hip hop was a cultural revolution that left an indelible mark on the music industry. The list of albums birthed in this era reads like a roll-call of hip hop royalty, each offering a distinct flavour of the genre’s dynamic roots and evolution. With Dr. Dre serving up ‘Nuthin’ But a G Thing,’ N.W.A.’s ‘Straight Outta Compton’ challenging societal norms, and The Notorious B.I.G.’s ‘Juicy’ serenading us with tales of triumph, the 90s showcased the diversity and depth that has come to define hip hop. The Fugees served their ground-breaking album with ‘Fu-Gee-La,’ and 2pac’s ‘All Eyez On Me’ uncovered street truths and introspective musings, while classics like ‘Rapper’s Delight’ became anthems of an entire generation.

On these albums, artists battled with identity, ambition, struggle, and success, weaving together narratives that reflected the African American experience with unflinching honesty and a compelling rhythm that resonated with listeners far beyond the confines of the inner city. The braggadocio of ‘Gangsta’s Paradise’ coexisted with the social commentary of ‘Fight The Power,’ just as the raw edginess of ‘Hypnotize’ sat alongside the smooth flows of ‘No Diggity’. It was a time when beatsmiths and wordsmiths collaborated to lay down tracks that evoked emotions and challenged societal constructs, a testament to the transformative power of the genre.

This golden age of hip hop was typified by a surge of creativity and raw talent that saw rappers going beyond just rhyming to plumb the depths of poetic expression. Albums from this era remain revered not just as music, but as cultural artefacts that encapsulate an era and continue to influence generations.

So let’s get into it. From the defiant roar of Public Enemy to the honeyed tones of Bone Thugs-n-Harmony, here are the best 90s rap songs that are must haves in your playlist.

66. Regulate – Warren G

A certified 90s hip-hop classic, no debate. This tune remains a paradigm of G-funk, a sub-genre of hip hop that amplified up the laidback West Coast vibes with the stethoscope of funk-infused soundscapes. Warren G’s silky rap delivery, paired with the soulful crooning of Nate Dogg, created a juxtaposition that enhanced the storytelling. The song’s narrative, a gritty and cinematic depiction of street life in Long Beach, California, was as intoxicating as its hook was catchy. In the broader context, “Regulate” was a vital stepping stone in defining the essence of West Coast hip hop, putting the G-funk era on the map, and boosting the Death Row Records legacy. It’s not just a throwback; it’s a musical time capsule.

65. It Was A Good Day – Ice Cube

This here is a certified classic, no debate. Ice Cube flipped the script on “It Was A Good Day,” painting a surprisingly tranquil scene of South Central LA. Cube dropped the hardcore gangsta persona for a minute to take us through a day where everything just fell into place, with no gang-banging, no cop hassles, just chilling out, maxing and relaxing. That Isley Brothers sample? Pure butter. Just goes to show, even the hardest emcees got their chilled out moments. But don’t get it twisted, it’s still street, still real, still Cube at his lyrical best.

64. Straight Outta Compton – N.W.A.

Straight Outta Compton – raw, visceral, unapologetic. Released in ’88 by N.W.A, it’s a classic cut straight from the streets, unfiltered, and right in your face. The track was ground-zero for gangsta rap, breaking down the door and serving up a brutal depiction of life in Compton. Dr. Dre’s production’s got that signature G-funk flavour, heavy on the low-end, laying the groundwork for a trio of lyrical heavyweights – Ice Cube, Eazy-E, and MC Ren – to spit fiery bars that left the world shook. It’s not just a song – it’s a cultural explosion that resonated far beyond the West Coast. “Straight Outta Compton” was reckless, defiant, and it revolutionised hip hop, if not all of popular music.

63. Gin And Juice (feat. Dat Nigga Daz) – Snoop Dogg

Straight from the boomin’ soundsystem of ’93 comes “Gin And Juice,” a quintessential G-Funk anthem from the Doggfather himself, Snoop Dogg. Peep those smooth, melodic synth lines and incontrovertibly dope grooves that define West Coast scene, courtesy of Dr. Dre’s production. Snoop’s narrative prowess is on full display here, spinning a tale of laid-back Cali living with a gangsta twist. With unparalleled flow, he paints a picture of backyard barbecues turned wild parties, a testament to his life in the LBC (Long Beach, California that is). Featured homeboy Dat Nigga Daz hops on for a verse, adding his flavour to this potluck of sounds. This jam ain’t just sippin’ on gin and juice, it’s sippin’ on the youthful, audacious spirit of 90s hip hop.

62. Hip Hop Hooray – Naughty By Nature

Yo, this track is like the national anthem for 90s hip hop heads. Released in ’93 on the album “19 Naughty III,” it’s a celebration of rap culture and served as a beacon for the East Coast hip hop scene. Treach, Vin Rock, and DJ Kay Gee’s ear for catchy, anthemic hooks is top tier – there ain’t many choruses from that era that get hands waving in the air like “Hip Hop Hooray, ho-hey-ho.” It blended insightful verses with a memorable chorus, creating a party atmosphere while keeping its roots grounded in the streets. This was a track that showed Naughty by Nature could balance mass appeal with street cred, no doubt. To this day, it remains a staple in any self-respecting rap playlist. Straight classic.

61. No Diggity – Blackstreet

That low rider anthem that had heads bobbin’ from its first chords. Oozing sultriness and a touch of the playa life, Blackstreet and Dr. Dre redefined the R&B infusion in hip hop with this 1996 monster hit off ‘Another Level.’ The real triumph of this cut was the inimitable voice of Teddy Riley, that man brought a sense of sophistication to hip hop that was missing in some quarters. The track’s smooth production, combined with its catchy hook, “I like the way you work it, no diggity, I got to bag it up,” is still unforgettable today. Shouts to that Bill Withers “Grandma’s Hands” sample that blessed it with extra soul. Did it change the game? No doubt.

60. All Eyez On Me – 2Pac

Nothin’ but a hip hop gem a 90s rap. The track gives us a taste of that raw unfiltered West Coast vibe that Pac was known for. From his unmistakable flow to the on-point production, this track had us all vibin’. 2Pac’s commentary on fame, street life, and breath-taking rise in the hip hop scene resonated with the realness of the era. This jam doesn’t hold back, confronting the harsh realities of the industry and society, a testament to 2Pac’s legendary status. In true Pac fashion, he served it straight no chaser, making it an undeniable classic of the decade. “All Eyez On Me” indeed continues to highlight ‘Pac’s enduring legacy in the annals of hip hop history.

59. Nuthin’ But a G Thing – Snoop Dogg

This is a respectable joint that was definitive of the G-Funk era. This laid-back track from Dr. Dre’s seminal “The Chronic” album had a young and hungry Snoop Dogg spilling lyrics smoother than silk. A synth-heavy banger, this cut was drenched in Southern California sunshine and street ethos, steering hip hop down a West Coast lane. Snoop’s flow was effortlessly slick, melding with Dre’s beats, showing us the power of true collaboration. While the language was raw, it painted a vivid picture of everyday life in South Central LA. This track was a game-changer – straight up – transforming hip hop and leaving a lasting impact. Hear it once, it stays with you. That’s the power of a ‘G’ thang.

58. Who Am I (What’s My Name)? – Snoop Dogg

Ayyo, let’s slide into the Dogg Pound, talkin’ bout “Who Am I (What’s My Name)?” by the big dogg himself, Snoop Doggy Dogg. Coming straight off “Doggystyle”, his 1993 debut album, Snoop put the G in G-funk with this single. Produced by the mastermind, Dr. Dre, that West Coast sound was smooth as California highways at dawn. With bouncy synths, laid-back bassline and a flow smoother than butter on a hot summer’s day, Snoop gave us an anthem that not only defined him as a player, but also set the tone for how gangsta rap could also be a party soundtrack. Nearly three decades later, this track still pops, reminding us why Snoop is a forever icon in the hip-hop game. The dogg’s clearly in the house, ya dig?

57. Hail Mary – Makaveli

Here we got “Hail Mary” by Makaveli, otherwise known as the late and great Tupac Shakur. This track dropped in ’97, posthumously, off the album “The Don Killuminati: The 7 Day Theory”. Ah, the mystique – every word laid down just before ‘Pac met his untimely demise. The haunting beat produced by Hurt-M-Badd, the prophetic lyrics, and the dark accompanying video; it solidified Tupac’s immortality in the game. “Hail Mary” ain’t just a song, it’s a rolling thunder that echoes Makaveli’s legacy. Pure ‘Pac – raw, intense, and brutally honest, refusing to sugarcoat the harsh realities of street life. This track is a testament to the undying spirit of one of hip hop’s greatest champions. Side note: Ain’t nothin’ coming close to that Outlawz feature. Pure fire!

56. Boyz-N-The-Hood – N.W.A.

Aight, strap in, as we rewind to ’87, when N.W.A. sent seismic waves through the hip hop scene with “Boyz-N-The-Hood.” Now, this track feels raw and rough around the edges, an unvarnished portrait of life in South Central LA. Eazy-E’s laid-back flow, like a homie telling stories on the stoop, talks of neighbourhood exploits, police harassment, and everything in between—the realities of the hood. But yo, it’s not just about the lyrics. Dr. Dre’s beat — that slow, bouncing, west-coast synth matched with a drum pattern that rivals a cardiac arrest — backs Eazy’s wordplay, creating a soundscape that’s as rough and unapologetically street as the lyrics. “Boyz-N-The-Hood” was more than a song; it was a hard-hitting social commentary, a gritty documentary in rhyme form. It didn’t just represent N.W.A.’s ethos, it reshaped the entire hip hop narrative. Respect.

55. Fu-Gee-La – Fugees

Fugees Straight outta ’96, “Fu-Gee-La” signifies the Fugees’ swagger-filled lane change from conscious rap into that raw, melodic blend that helped shape the mid-to-late 90s sound. Pras, Lauryn Hill, and Wyclef Jean carve out their own niches in this track, with a reggae-tinged beat making the perfect backdrop. Hill’s verse alone demands multiple rewinds, mastered in both flow and lyrical finesse. But let’s not sleep on Jean and Pras either – their deliverance oozes a gritty reality that contrasts Hill’s emotional intensity. It’s a testament to the trio’s chemistry, that despite their vastly different styles, they come together in a symphony of street symposium, pure heat. “Fu-Gee-La” escalated the Fugees from underground gems to hip hop royalty, lacing us with a timeless classic.

54. 2 Of Amerikaz Most Wanted – 2Pac

2Pac in his rawest form, going bar for bar with the D-O-double-G, Snoop Dogg. Straight off Pac’s monstrously successful double disc “All Eyez On Me”, this track is a certified banger! Both these West Coast titans unleashed seismic flows over a G-funk rhythm that could shake Compton to the Bay. The lyrics were unapologetically brazen, embodying the outlaws that both rappers claimed to be. Now, while it may not have shown the heartfelt poet that Shakur often was, it revealed the unflinching resolve of an artist refusing to be overshadowed by his demons or his drama. “2 Of Amerikaz Most Wanted” affirmed 2Pac’s reign in hip hop, squashing anyone who doubted his turf in the rap game.

53. Fuck Tha Police – N.W.A.

N.W.A’s protest anthem “Fuck Tha Police” makes a staggering impact. The track is as politically charged as a Molotov cocktail. Straight off their 1988 album “Straight Outta Compton”, it’s an adamant, aggressive, anti-establishment spitfire replete with confrontational verve. It reflected the frustrations of Black America with police brutality and systemic oppression, becoming a battle cry for the disenfranchised. While some saw it as a glorification of violence, true heads understood the profound systemic critique it represented. Still, decades later, its potency and relevance remains. FYI: it’s not about promoting lawlessness, it’s about demanding justice. A watershed moment for hip hop culture, this track definitely earned its stripes. But be warned, it ain’t for the faint-hearted!

52. Gangsta Gangsta – N.W.A.

Blowin’ straight outta Compton, N.W.A.’s “Gangsta Gangsta” is a powerful declaration of street poetics capturing the perils of living in ’80s West Coast hoods. Ice Cube’s untamed flow coupled with Dre’s booming beats bridge the gaps between gritty realities and hip hop fantasies. It’s a raw representation of their world, fusing elements of storytelling with gangsta braggadocio. Some critics might frown at its explicit content, but ain’t no denying, it painted a vivid picture of Compton’s underrepresented. And let’s keep it 100, without “Gangsta Gangsta”, which arguably pioneered the gangsta rap genre, we might not have had the storied Rap scene we see today. Loaded, controversial, but undeniably influential. That’s “Gangsta Gangsta” for ya!

51. Ready or Not – Fugees

This one’s a straight-up classic track from the legendary trio of Wyclef, Lauryn Hill and Pras. They flipped that Delfonics sample and made it their own, spitting a socio-political dialogue that was fiercely progressive for its time. Lauryn Hill’s vocal performance? Chills, fam. Her melodic flow and raw lyricism are pure fire, addressing life in the hood and the world at large. Wyclef and Pras hold it down too, adding their unique styles to the mix. This track has that 90s rap boom-bap aesthetic nailed down, reminding us of a golden age when hip hop was all about storytelling and spreading knowledge. Straight facts, no cap.

50. Passin’ Me By – The Pharcyde

“Passin’ Me By” by The Pharcyde: Yo, kick back and chill as we take a ride down memory lane with this quintessential 90’s joint. “Passin’ Me By” is the zenith of The Pharcyde‘s off-kilter aesthetic, amalgamating mellow, jazz-laden beats with the lyrical prowess of MCs passing round the mic like a hot potato. They spit tales of unrequited love with a dose of dauntless honesty and a quirky flair that epitomizes the classic 90s alternative rap scene. The Pharcyde’s ability to marry humour with heartbreak is what sets them apart from the pack – there ain’t no sugarcoating here, just realness wrapped in a beat that’s boundary-pushing even by today’s standards. This joint’s raw emotion hits home like a sucker punch that leaves you wanting more. Don’t sleep on this track, homies!

49. Feel Me Flow – Naughty By Nature

When Naughty by Nature dropped “Feel Me Flow” in ’95, it was like a summer BBQ on wax. It came off their fourth album “Poverty’s Paradise,” bringing in that laid back, feel-good vibe, wrapped in Treach’s quickfire rhymes and Vin Rock’s smooth delivery. No doubt, it was an essential jam in the era of ’90s boom-bap. But here’s the caveat, folks: “Feel Me Flow” was like that tasty dessert after a heavy meal — delightful, but not quite providing the substance you’d expect from a group that brought us “O.P.P” and “Hip Hop Hooray”. So, while it’s a feel-good anthem for sure, it doesn’t quite hit the same heights as their earlier, grittier work. Never the less, it’s well worthy of its spot on this list.

48. Thuggish Ruggish Bone – Bone Thugs-N-Harmony

Now here’s a joint we can’t overlook. This cut by Bone Thugs-N-Harmony off their debut EP, ‘Creepin on ah Come Up’, helped put Cleveland on the hip hop map in ’93. The rapid-fire, melodic harmonizing flow of Krayzie, Layzie, Bizzy, Wish and Flesh was straight refreshing at the time. This tune laid the foundation for their unique style that blended G-funk vibes with a Midwestern twist. The lyrics? Pure street hustle peppered with spiritual undertones, straddling the line between sinners and saints. “Thuggish Ruggish Bone” was our introduction to these ‘street soldiers’ and their journey to escape the struggle. An unquestionable classic in the annals of 90s hip hop.

47. Me, Myself & I – Various Artists

A definitive track from De La Soul’s groundbreaking album “3 Feet High and Rising”. This tune took the hip hop game by storm in ’89, introducing us to De La’s unique brand of conscious, sample-heavy rap. We ain’t only talking hip hop beats here, but lyrical content too – Plug One (Posdnuos), Plug Two (Dave), and Plug Three (Mase) showed they could hold their own against the hardcore lyricists of their era without resorting to gun-talk or gangster posturing. Instead, they celebrated individuality and perspective, encouraging listeners to “say no go” to conformity. It’s a witty, introspective joint that remains a classic in 90s hip hop – if you don’t know, now you know!

46. Planet Rock – Afrika Bambaataa

This ain’t just a song, it’s a whole movement encapsulated in six minutes of synth-drenched glory. Birthed in ’82, smack dab in the genesis of the hip-hop era, this aural masterpiece rode on the wave of Roland TR-808 drum machine loops that still hold their weight today. Bambaataa didn’t just borrow from Kraftwerk’s “Trans-Europe Express”, he straight up interweaved it into the core of the track, proving sample-based music ain’t thievery, but an art form of its own. “Planet Rock” ain’t just a classic, it’s a game-changer, one that shifted the tectonic plates of rap and injected it with a dystopian, electronic fervor that still resonates. We snuck this one in along with a few others despite not being released in the 90s…. sssh!

45. Let Me Blow Ya Mind – Eve

This sizzling joint was a long-awaited collaboration between Eve and Gwen Stefani, two absolute queens from divergent music scenes. Produced by Dr. Dre and Scott Storch, it’s a masterclass in restraint, with a minimalist beat that lets Eve’s gritty flow shine. The song pushed the limits of traditional hip hop with its rock/pop influences, bridging the gap between genres in a way that was uniquely late 90s. Yet, Eve never loses sight of her roots, her verses bristling with the same raw energy and streetwise swagger that she brought to the Ruff Ryders. Let this be said, Eve was never here to play; she stepped into the world of hip-hop to dominate. And with “Let Me Blow Ya Mind”, she did just that.

44. Rapper’s Delight – The Sugarhill Gang

Would you believe this jam was dropped in 1979 and was the first rap single to crack the Top 40 on the Billboard Hot 100. ‘Delight’ brought hip hop out the Bronx and into suburbia, making it a global movement. Big Bank Hank, Wonder Mike and Master Gee, although not lyrically profound as Rakim or Nas, their nursery-rhyme style of rapping was infectious and had a universal appeal. The funky bassline, sampled from Chic’s “Good Times”, provided the perfect backbone for the emcees to spit their lighthearted rhymes. An essential part of any old school rap playlist. Aiight, it’s not a 90s rap tune, but it deserved a mention!

43. Funky Cold Medina – Tone-Loc

This dropped in ’89 but it’s no doubt one of the defining sounds of early ’90s hip hop. You see, Medina ain’t no woman, folks. It’s a love potion, a liquified charisma that Tone-Loc taught us about. The track’s crazy fun narrative combined with an infectious beat, man, it’s like a party packed into 4 minutes and 9 seconds. However, some of the song’s content, especially around women, hasn’t aged well. While we can jam to the groove and throw our respect to its place in hip hop history, we gotta also recognize its flaws. Ain’t no rose without its thorns, right?

42. Apache (Grandmaster Flash Remix) – Various Artists

Dropping the needle on the table with an old school bravado that’s hard to match. Grandmaster Flash, the heralded godfather of hip hop, took the Incredible Bongo Band’s breakbeat classic, “Apache,” and gave it the deft remix treatment. Flash’s dexterous hands flipping the groove into an irresistible call to the dance floor is a home run for all true hip hop heads. The track is a high-octane sonic arrow, catapulting listeners into a true school hip hop cosmos. His remix upped the ante, looping tantalising cuts of the original funk-laden baseline, and weaving in salient drops of the iconic drum rhythms. This track ain’t just a song; it’s a force of nature in the hip hop scene. Remember, you don’t just listen to “Apache,” you feel it!

41. I Get Around – 2Pac

A certified West Coast classic. This track, featuring Shock G and Money-B of Digital Underground, is a gleeful celebration of Pac’s playboy lifestyle. Tossing aside the sociopolitical commentary he’s known for, Pac hops in with a smooth player’s charm. The production on this is crazy dope too, with a funk-infused beat that screams Cali vibes. But let’s not sleep on the lyrics; Pac’s bravado and charisma are on full display. And that hook? Pure gold. This one isn’t just a crowd mover, it’s a stamp on the map showing where Pac was heading.

40. Hey Ya! – Radio Mix / Club Mix – Outkast

‘Hey Ya!’ by Outkast sneaks into our list despite being released in ’00… as this track rules with its infectious beat and irresistible call to “shake it like a Polaroid picture”. For real, the joint’s so good it catapulted Andre 3000 and Big Boi into the stratosphere, beyond the Dirty South they championed. While “Hey Ya!” may not embody the grittiness typically associated with ’90s hip hop, its genre-blurring, rule-breaking attitude meshes perfectly with the era’s spirit of experimentation and boundary-pushing. However, its placement here is a clear reminder that while you can make a banger, you can’t rewrite history. This party crasher is just a little out of sync.

39. Ambitionz Az A Ridah – 2Pac

“Ambitionz Az A Ridah,” the opening salvo from 2Pac’s “All Eyez on Me” (Death Row, 1996), encapsulates the seismic shift the iconic rapper underwent after his prison stint. 2Pac emerges more confrontational, his fiery spirit funneled into a relentless drive that matches the song’s pounding West Coast G-Funk beat. The cut is a testament to Shakur’s lyrical prowess and unshakeable swagger. Its relentless tempo, unforgiving drums and hypnotic synths provide the perfect sonic runway for Shakur’s raw and aggressive verses. Amidst the heavy beats, what really hits hard are his lyrics, unapologetically exposing the dark realities of street life. It’s a track that exemplifies 2Pac’s evolution, and it indeed stands tall as a cornerstone of 90s hip-hop.

38. Gangsta’s Paradise – Coolio

Straight from the heart of Compton, we kick off with a a classic from the soundtrack of the 1995 film “Dangerous Minds”. Coolio’s “Gangsta’s Paradise” is a bleak, yet masterful portrayal of street life. Coolio’s bars, layered over a sample from Stevie Wonder’s “Pastime Paradise”, created a juxtaposition of grit and melody that pulled in listeners like a magnet. The song took Coolio to the apex of the charts, towering as a numero uno on the Billboard Hot 100. Despite its success though, it never escaped the shadow of its filmic tie-in, which could arguably be the reason it sits in the last spot on our list. Before autotune and mumble rap lurked in every corner, this was the raw, unfiltered sound of the streets.

37. Step into a World (Rapture’s Delight) – Boogie Down Productions

KRS-One under Boogie Down Productions snapped when he combined Blondie’s “Rapture” with his hard-hitting verses. KRS-One’s lyrical mastery does a mad tango with the unmistakable guitar riff, proving hip hop’s incredible sampling capabilities. Tell a man to pick his favourite hip hop track and you just might hear this banger in reply. While KRS-One is often painted as an educator, make no mistake, he can spit rhymes with the best of them. If you’re yearning for some old school hip hop, this joint deserves a prime spot on your playlist.

36. Fight The Power – Public Enemy

Man, ain’t nothin’ quite emblematic of that boisterous, defiant spirit of hip hop like Public Enemy’s “Fight The Power.” This ferocious anthem ain’t just a track, it’s a manifesto, sparking rebellion against societal ills. Chuck D, Flavor Flav and the crew threw down a blistering critique of systemic oppression, calling on peeps to shake off them chains. Reflecting the roiling tensions of late ’80s America, the song was both a nod to Isley Brothers’ original and a trailblazing beast all its own in the golden era of hip hop. Sporting bomb squad’s seismic production, it’s an audacious, galvanising force, inverting power structures and advocating resistance. Word, this joint ain’t just music, it’s a revolution!

35. The Message – Grandmaster Flash & The Furious Five

An intriguing spin on the original classic by Grandmaster Flash and The Furious Five. Released in the 90s, this version maintains the track’s truth-telling ambition, with its powerful lyrics laying bare the essence of city life in a raw, uncompromising manner. The re-recording stays faithful to the original’s thunderous beat and distinctive rhymes, but brings a fresh edge with tighter production values. It’s an essential aspect of hip hop’s evolution, a testament to the resilience of the genre and its ability to adapt and recharge. Even though it’s not as revered as the classic, any hip hop head would tell you, it’s still “like a jungle sometimes, it makes me wonder how I keep from going under”.

34. La-Di-Da-Di – Slick Rick

In this count-up of dopest 90s hip-hop jams, we got the Slick Rick classic, “La-Di-Da-Di”. A yesteryear jewel that showed us just how storytelling should be done in a hip-hop track. This track, with its iconic “La-Di-Da-Di, we likes to party” hook, didn’t just give birth to numerous samples and remakes – no sir, it straight up influenced generations of MCs. Slick Rick, with his unique, laid-back delivery and vivid, off-beat narrative style, proved that hip hop wasn’t just about the hard-boiled streets, but can also be a playground of tales and fantasies. Now that’s what’s up!

33. Paid In Full – Eric B. & Rakim

It ain’t just a song, it’s was a movement, this joint is a cornerstone in the building of hip hop’s golden age, with Rakim’s laid-back yet intricate flow over Eric B.’s soulful, James Brown-infused beat sandwiching perfectly. Rakim’s lyrics are a testament to ambition and the hustle, offering a raw insight on the pursuit of wealth. The refrain, “thinking of a master plan, ’cause ain’t nothing but sweat inside my hand”, became an anthem for the struggle, the grind, and the ultimate come-up in inner city life. No doubt, “Paid in Full” is hip hop in its truest form. It’s the blueprint, beloved!

32. The Message – Extended Version – Grandmaster Flash & The Furious Five

Grandmaster Flash & The Furious Five is a cornerstone in the hip-hop realm, no doubt. This extended cut is a living testimony of how rap evolved to reflect the harshest societal realities. The Furious Five and Melle Mel were laying down lyrics more reminiscent of a gritty social commentary than a catchy club tune. The dystopian ’80s Bronx narrative was uncensored and unapologetic, rhyming all the way through the ’80s and ’90s. It’s ‘don’t push me ’cause I’m close to tha edge, I’m trying not to lose my head’ refrain is iconic in itself, underpinning the inner city angst and fragile mental state. It’s anything but a happy party jam, but in its blunt depiction of street life, it’s a storytelling masterpiece that set the tone for conscious rap.

31. It’s Like That – Run–D.M.C.

The game-changers, Run-DMC, simply declared “It’s like that, and that’s the way it is”. Another one before it’s time being released in 1983, redefined the hip hop landscape and rode a way into 90s rap culture with its raw energy and social commentary. Dropping truth bombs right out the gate, Run, DMC and Jam Master Jay didn’t hold back, speaking on the harsh realities of urban life. They scrapped the disco and funk influences that were prevalent in hip hop at the time, embracing instead an unadorned, stripped-down style drawn straight from the streets. No fancy hooks, no frills – just hard-hitting beats and poignant rhymes. The track’s influence is indisputable, setting the stage for a new era of hip hop driven by realness and authenticity.

30. Bow Down – Westside Connection

The trio of Ice Cube, WC, and Mack 10, really encapsulates that unapologetic 90s gangsta rap vibe. This was the West Coast staking its claim, serving notice to the rest of the Hip Hop world, demanding respect – ain’t no polite request, it was a demand “Bow Down”. The track’s production, crisp and hard-hitting, kind of like a Michael Mann movie scoring a drive-by, is an integral part of the package. Ice Cube’s verse in particular carries that heavyweight champion swagger, verbally jousting any potential rival daring to step up. Yes, the bravado might seem heavy-handed, but you gotta remember the context, the mid-90s rivalry, the East Coast/West Coast beef, this was a frontline anthem. As an assertion of regional dominance, “Bow Down” was downright seismic.

29. Let Me Clear My Throat – DJ Kool

Now, this ain’t just your regular hip hop joint, it’s a wild concoction of raw energy, crowd interaction, and old-school funk sampled perfection. Kool had the unique gift of turning his live performances into studio magic and this joint is living, breathing evidence of that. Threading together Go-Go beats that the DMV area is known for, with a James Brown funk backbone, Kool delivers a chant-along classic that still resonates with its infectious energy. Significant in marking the transitional period between golden era boom-bap and the emerging party-centric anthems of the late 90’s, this cut reminds us never to underestimate the power of a hype crowd, a nimble emcee, and a funky beat. The perfect formula for hip hop euphoria.

28. People Everyday – Metamorphosis Mix – Arrested Development

Whilst rolling through the ’90s hip-hop scene you can’t miss this banger by Arrested Development. Oh boy, this jam is a real head-noddin’ classic. It’s all about that laid-back groove, with the vocals taking you on a metaphorical journey about the black experience in America. Speech’s lyrics offer a poignant narrative, laced with social commentary that speaks up against the labels and stereotypes faced. And that catchy hook, sampling Sly & the Family Stone’s ‘Everyday People’, cements the track’s status as an evergreen hip-hop anthem. It’s not just a bop, it’s a testament to hip-hop’s power in giving a voice to the voiceless. Chilled-out yet thought-provoking, ‘People Everyday’ brings some much-needed consciousness to the rap game.”

27. Ruff Ryders’ Anthem – Re-Recorded – DMX

When DMX barked these lyrics, there was no doubt that the Yonkers MC was here to disrupt the game. Emerging as a tour de force in the post-Biggie, post-Pac era, DMX’s raw, gritty street narratives and ferocious growls added a new layer to 90s hip hop. The track, with its pounding, synth-driven hook by a young Swizz Beatz, further established the Ruff Ryders collective as a hip-hop powerhouse. The re-recorded version doesn’t lose any of the original’s fury, delivering a stomach-churning mix of dark, relentless energy and stark realism. This wasn’t just a song, it was a war cry, and marked DMX as one of hip hop’s most distinct voices. DMX didn’t just bark, he bit.

26. Shake Ya Ass (feat. Pharrell Williams) – Mystikal

Ain’t no doubt that Mystikal’s “Shake Ya Ass” had the youth of the 90s getting jiggy on the dance floor. With its infectious rhythm and bounce, accentuated by Pharrell’s signature Neptunes beat, it was an anthem that felt like a party unto itself. But dig a little deeper and you’ll find more than just a dance track. It was Mystikal’s growling, almost raspy delivery that set him apart from his counterparts, a blueprint he’d later expand on. Love it or hate it, this track was a key player in ushering in the era of the New South in hip hop.

25. Express Yourself – Remix – N.W.A.

“Express Yourself – Remix” by N.W.A. broke the mould, no doubt. It’s an old school banger that packed a punch of social commentary. Public sentiment was usually against N.W.A for their street-oriented, often violent lyrics. But yo, this track flipped that script with a message about freedom of speech and individuality. Over a funky, brass-heavy beat reminiscent of the funkadelic vibes, Dr. Dre took lead on the mic, an unusual move considering his primarily production-focused role. Despite its positive message, it still rocked that quintessential defiant N.W.A attitude. It may not possess the raw lyrical insight of ‘Straight Outta Compton’ or the aggressive protest of ‘Fuck tha Police’, but it’s still a vital part of N.W.A’s illustrious yet controversial legacy.

24. N.Y. State of Mind – Nas

“N.Y. State of Mind” off Nas’s 1994 debut album “Illmatic” is straight fire. This ain’t just a bold claim, it’s a fact! This cut is a blueprint in storytelling, with Nas lyrically painting a picture of his gritty, crime-riddled New York environment. The dark and gritty production from DJ Premier sets the stage for one of the most vivid narratives in hip hop history. With lines like, “I never sleep, because sleep is the cousin of death,” Nas’s depiction of the harsh realities of street life is as poetic as it is harrowing. A groundbreaking masterpiece, “N.Y. State of Mind” cemented Nas as a lyrical genius and remains a benchmark for conscious rap to this day.

23. Gravel Pit (feat. RZA, Method Man, Ghostface Killah, Raekwon & U-God) – Wu-Tang Clan

The iconic collective from Staten Island caused a seismic shift in the soundscape of 90s rap. Dropping in the cataclysmic year of 2000, this track is a shape-shifter! It blends traditional rap elements with an old school kung fu vibe, layered upon a mesmerising synth line. Wu’s Supreme Necklace Rap King, RZA, conducts this sonic orchestra with mastery, while Method Man, Ghostface Killah, Raekwon and U-God come with relentless bars. This tune paved the way for the Clan’s unusual, innovative style that was more Shaolin meet Marvel Comics than South Bronx. A banger that reminds us of the genre’s capacity for evolution and experimentation. “Gravel Pit” – where the raw grit of hip hop meets the shimmering future.

22. It Takes Two – Rob Base & DJ EZ Rock

Dropped in 1988, we be stepping back to the days when Hip Hop was still a young gun. No doubt, this joint symbolises the syncopation of hip hop and dance, with a thumping beat sampled from Lyn Collins’ “Think (About It)”. Let’s face it, the lyricism ain’t Pulitzer quality, but the infectious beat and brazen celebration of pure joy got folk up and off their seats. They ain’t setting the world on fire with treacherous wordplay or activist rhymes, but they repped the fun, party rocking element of hip hop. This cut will forever blast from BBQs, block parties and blowout celebrations, proving that sometimes, it’s simplicity that slaps the hardest.

21. How I Could Just Kill a Man – Cypress Hill

The notorious track, “How I Could Just Kill a Man,” off Cypress Hill’s 1991 self-titled album introduced the world to their smoky, latently violent brand of hip hop. B-Real’s nasally delivery and DJ Muggs’ funky, bass-dropping beats created an infectious musical pairing that captivated the streets and burbs alike. The track delved into the simmering frustrations of hood life — a raw reality check that didn’t shy away from addressing violent urges. Even though it emerged during a time when gangsta rap was blooming, this track still managed to stand on its own, punctuating its message with an earth-shaking exclamation point that Cypress Hill was an act to be reckoned with.

20. Summertime – DJ Jazzy Jeff & The Fresh Prince

“Summertime” by DJ Jazzy Jeff & The Fresh Prince is more than just a song, y’all—it’s an ethos. Released in 1991, this jam captured the carefree spirit of the season, making it an evergreen classic. You can’t deny the smooth flow of young Will Smith, AKA The Fresh Prince, bobbing and weaving around jazz samples with grace. Man, when he spits “Here it is the groove slightly transformed / Just a bit of a break from the norm,” you feel it in your soul. And let’s not forget DJ Jazzy Jeff spinning the vibes behind the decks, providing that mellow, laid-back beat. This song remains a staple not just in ’90s hip hop, but within the broader cultural memory of the season itself. If this ain’t the theme song for summer, I don’t know what is.

19. The Message – Nas

Ayo, hip hop heads. Let’s talk about Nas’s spin on “The Message”. It’s not every day you hear a maverick stepping in the footprints of Grandmaster Flash and The Furious Five’s joint. But Nas? This Queensbridge emcee did it justice – flipping the narrative to lace his own struggles and achievements. No sugarcoated truths here, just raw statements about street life. The track flies with Nas’s thought-provoking lyrics and jazzy, hypnotic loops. But, let’s be real, it ain’t got the same revolutionary guts that made the original “The Message” a cornerstone in the hip hop fabric. Still, props to Nas for adding another layer to an iconic hip hop narrative. His version offers a fresh take on the struggles in the concrete jungle, keeping it 100. Hip Hop needed this.

18. Runnin’ – The Pharcyde

A testimony to the genre’s ability to fuse soulful introspection with lyrical dexterity. Lifted from their ’95 classic, “Labcabincalifornia,” it’s a track that dissects their personal battle with adversities, boosted-up by J Dilla’s ingenious beat flip of Stan Getz’s “Saudade Vem Correndo.” It’s the struggle and growth summed up in a sonic narrative capturing raw human experience. They don’t make ’em like this no more! The West Coast collective painted a masterpiece where every rhymed bar served as a brush stroke on a canvas depicting their journey to escape life’s endless chase. “Runnin'” was the ’90s hip hop taking a deeper, more introspective turn – and it was a damn good one.

17. Ghetto Supastar (That is What You Are) (feat. Ol’ Dirty Bastard & Mýa) – Pras

A shimmering gem of hip hop history. Released in ’98, this joint was the brainchild of Fugees member Pras, featuring an off-the-cuff verse by the late eccentric genius Ol’ Dirty Bastard and vocals by Mýa. The track was a crucial part of the soundtrack for the political flick “Bulworth,” and boy, did it amplify the movie’s mood. Pras’ verse is a lyrical finesse, while ODB’s uncut delivery added a raw edge. Mýa’s smooth vocals on the hook were the icing on this hip hop cake. Blending elements of pop and hip-hop, the song added a touch of mainstream appeal to the gritty reality of the ghetto lifestyle. Chill but conscious, “Ghetto Supastar” is 90s brilliance at its best.

16. Intergalactic – Remastered 2009 – Beastie Boys

This track has the Beastie Boys cementing their place in hip hop history, blending old school rap styles with futuristic sounds like nobody’s business. The track, straight from their album ‘Hello Nasty,’ is packed with eccentric lyrics and a hook that sticks in your head like a catchy pop refrain. The Beasties channel their spacey, off-kilter persona throughout the track, bringing fresh dynamism to the 90s hip hop scene. This trailblazer tune catapulted the trio into the chart stratosphere, proving that rap could stretch its muscles and take on an interstellar journey, all while retaining its rhythmic roots. As songs go, homies, this joint is lightyears ahead.

15. It’s Tricky – Run–D.M.C.

This was dropped in ’86 and was a turning point for the culture that reverberated into the 90s rap scene, and “King of Rock” and “Walk This Way” had already shown that Run-DMC didn’t just break boundaries – they smashed ’em. Then they dropped “It’s Tricky,” a cheeky, bold joint off “Raising Hell”, weaving braggadocio rap over that killer Knack “My Sharona” sample. It’s a playful jab at the complexity of maintaining authenticity in the limelight, a struggle still echoed in today’s culture – maintaining that balance between your roots and the lure of the almighty dollar. The track is proof positive of the trio’s undeniable influence on the development of hip hop. Man, they weren’t just rappers, they were trendsetters, forging a path for the genre to step into the mainstream.

14. If I Ruled the World (Imagine That) – Nas

A political statement cunningly disguised as a breezy summer joint. Nas, that poetic prophet from Queensbridge, hooked up with the Fugees’ Lauryn Hill in ’96 to craft this gem. The track, hailing from his “It Was Written” album, synthesizes Nas’ raw lyricism with Lauryn’s soulful melodies, embodying the often-omitted conscious side of 90s hip hop. Nas imagines a world without the systemic oppression faced by marginalised communities, creating a blueprint for the utopia he’d construct if he had the power. It can’t be denied, this track isn’t just another hip hop song; it’s a vibrant manifesto for a brighter future.

13. Survival of the Fittest – Mobb Deep

Lace up ya Timbs and strap on ya bulletproof vest ’cause we steppin’ into the Infamous era of Queensbridge. “Survival of the Fittest” is a raw testament to Mobb Deep’s aptitude for crafting atmospheric, gritty tales all about life on the streets. This ’95 banger off their critically hailed album ‘The Infamous’ got heads bobbing and ears perking up all over the Big Apple. Powered by Havoc’s gloomy, haunting beats and Prodigy’s stone-cold rhymes about the realities of their jungle, this cut solidified their place in the echelon of 90s Rap East Coast hip-hop royalty. The remarkable blend of Havoc’s production prowess and Prodigy’s lyrical venom birthed a paradigm-shifting anthem for all the hood soldiers trying to survive their concrete jungles.

12. Check Yo Self – Remix – Ice Cube

A prime cut from Ice Cube’s catalogue, son. It’s got the West Coast G-Funk that Cube spearheaded as a solo artist, warning fake gangsters about the consequences of their actions. Sampling Das EFX’s “They Want EFX,” the track hits with an infectious beat that invites everybody to bob their heads. Cube comes correct with his signature hard-hitting bars that throw shade and celebrate street realities. The remix, produced by DJ Pooh, takes it up a notch with a killah bassline and slick cuts. A classic joint that defined the 90’s tough-talking, reality-based gangsta rap era. Don’t get it twisted, fam, if you’re new to the game, this track’s a good starting point.

11. I’ll Be Missing You (feat. Faith Evans & 112) – Diddy

Puff Daddy, Faith Evans & 112… oh my… ya feel me? Sometimes, hip hop ain’t just about the boom-bap, it’s about expressing emotion in the rawest form. And nobody did that better than Puff Daddy, Faith Evans, and 112 with “I’ll Be Missing You.” A tribute to the fallen soldier: the irreplaceable Notorious B.I.G. Puff Daddy’s verse dropped like teardrops on the mic, and Faith Evans rendered the hook so raw, it’ll leave your heart stinging. This track is a monumental example of the depth 90s hip hop could reach, connecting with fans on a level deeper than your average club banger. It ain’t the grittiest hip hop track, but its emotional resonance is undeniable.

10. Can I Kick It? – A Tribe Called Quest

A Tribe Called Quest dropped this joint in ’90, stirring waves in the hip hop scene. It’s the perfect fusion of jazz and hip hop, serving as a testament to Tribe’s future-forward vision. Utilising Lou Reed’s ‘Walk on the Wild Side’ sample, they showcased their knack for blending diverse musical influences. It ain’t just the beats though – the lyrics are a sequence of effortless cool, from the signature call-and-response of the title to skillful verses. While it ain’t the hardest track, “Can I Kick It?” symbolises Tribe’s easy-going, intellectually stimulating vibe. It’s a classic – no argument.

9. Still Not a Player (feat. Joe) – Radio Version – Big Pun

A stone-cold classic from the late, greater-than-great Big Pun. This radio version, featuring Joe, was a monolithic statement in the rap game when it hit the airwaves in ’98. Combining Pun’s intricate rhymes and irreverent, unapologetic attitude with Joe’s smooth, buttery vocals, it was a radio-ready banger that still had serious street cred. It’s a prime example of an MC at the top of his game showcasing playful braggadocio and unabashed charisma. While Big Pun left us too soon, this joint remains a solid testament to his unique style and irreplaceable talent. A quintessential track of the late 90s golden era.

8. No Sleep Till Brooklyn – Beastie Boys

A hard-hitting ode to New York’s most populated borough, riding an incessant, thrashing guitar riff courtesy of Slayer’s Kerry King, the Beastie Boys melded punk rock ferocity with hip hop lyricism to create a sound that was nothing short of revolutionary. This joint’s raw energy and headbanging appeal embodied the rebellious spirit of the 90s hip hop scene, pushing boundaries and breaking down genre walls with gusto. Whether you’re a hip hop head or a metal fan, “No Sleep Till Brooklyn” reminds us of a time when the two seemingly disparate worlds united under the genre-defying banner of the Beastie Boys.

7. I Got 5 On It – Luniz

This joint right here is a bona fide classic! Crafted in ’95, Luniz dropped this gem on their album “Operation Stackola” and straight up ran the airwaves. This Oakland pair, Yukmouth and Numskull, weren’t playing games, unspooling tales of street life over a smooth-ass beat sampled from Club Nouveau’s “Why You Treat Me So Bad”. The hook? Catchier than a cold, son. And let’s not front, we all know what that ‘5’ stands for. More than just a weed anthem, it spoke volumes about the social and economic realities in the ‘hood. “I Got 5 On It” ain’t just a song, it’s a cultural moment and remains a quintessential slice of that ’90s hip hop pie. Straight fire!

6. Mo Money Mo Problems (feat. Puff Daddy & Mase) – 2014 Remaster – The Notorious B.I.G.

This joint right here is pure, unadulterated ’90s hip hop gold. A chart leader from Biggie’s “Life After Death”, “Mo Money Mo Problems” encapsulates the paradox of success that defined the East Coast rap legend’s career. With a hook that’ll be ringing in your ears long after the track ends, Mase and Puff Daddy go verse-for-verse with the late, great Notorious B.I.G. In true Bad Boy fashion, the track samples Diana Ross’s “I’m Coming Out” for the beat, an insidious earworm that’s both playful and poignant. Even in remaster, Biggie’s verses hit with the same ferocity and intricacy, reminding us why he was crowned King. Unfailingly, it’s a crucial piece of hip hop’s golden age tapestry.

5. Juicy – The Notorious B.I.G.

A classic by The Notorious B.I.G., is easily one of the defining tracks of ’90s hip hop. Biggie’s silky flow over a smooth Mtume sample gives us a vivid depiction of his rags-to-riches story, capturing the essence of hip hop as aspirational music. The track resonated deep in the heart of the urban streets, and projected Biggie’s voice to the global stage. His storytelling finesse shows just why he’s considered one of the greatest lyricists of all time. His running commentary on the socio-economic issues faced by African-Americans, coupled with his ambition and bravado, makes “Juicy” a quintessential hip hop anthem. Straight up, this joint is synonymous with Biggie’s legacy.

4. C.R.E.A.M. (Cash Rules Everything Around Me) (feat. Method Man, Raekwon, Inspectah Deck & Buddha Monk) – Wu-Tang Clan

An outright blessing, an anthem – a statement. This joint dropped ’94 and it was a game-changer, versifying the unadulterated street hustle. Genius from Shaolin’s finest, this track got Method Man on the hook, and formidable verses from Raekwon and Inspectah Deck that encapsulate the raw grit of the ghetto. The strong, stripped-down beat is RZA’s own, still echoing in the hip-hop culture, but let’s not forget Buddha Monk, lending a desperate eeriness with his haunting background vocals. This quintessential Wu-Tang expression is a stark chronicle of the urban survival struggles, showing how paper chase dominates everything. If ever there was a soundtrack to hood ambition, this is it, fam.

3. Return of the Mack – Mark Morrison

This smooth cut dropped in 1996 and forever immortalised Morrison in the halls of 90s hip hop. The overall vibe is nuanced yet undeniably catchy, layering R&B rhythms with hip hop sensibilities. It’s the track’s hook that catches you, a sonic earworm that never fails to transport you to a time of baggy jeans and music videos on MTV. Notably, the track served as an assertion of Morrison’s own comeback, a nod to his turbulent personal life, making the track resonate beyond its infectious beat. Despite Morrison’s disappointing lack of follow-through, there ain’t no denying – “Return of the Mack” defined an era.

2. Shook Ones, Pt. II – Mobb Deep

The epitome of gritty, grimy, 90s East Coast rap. Havoc and Prodigy, masters of depicting the realities of Queensbridge, birthed a seminal anthem for the hood. This track’s influence is undeniable – its cold, menacing instrumental and vivid street narratives paved the way for countless imitators. There ain’t no such things as halfway crooks, they declared, shedding light on the difference between those who merely pose and those who live the life. A masterclass in storytelling, this track’s not just an appealing head-nodder, it’s a parable about survival in the most intense environments. Urban poetry at its finest.

1. Hypnotize – The Notorious B.I.G.

More than a track; it’s a time capsule of the golden era of hip hop. Fresh off Bad Boy Records, this jewel doesn’t just slap, it reverberates through the annals of hip hop history. Biggie’s unparalleled lyrical prowess and charismatic delivery ensured the jam went down smooth. Factor in the slick production from beatsmith Puff Daddy, and the result was a hypnotic triumph that topped Billboard’s Hot 100. This track is Biggie’s legacy, perfectly blending his street-poet wisdom with his opulent vision – a testament to both his harshest realities and his wildest dreams. It’s a self-fulfilling prophecy for the King of New York; his reign may have been tragically cut short, but music like this ensures he’ll be remembered as hip hop royalty forever.

A good friend put this all into a Spotify Playlist making it a real go-to at any time of day, it’s an absolute must have in your saved list.

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