Sugarhill Gang - Rapper's Delight (1979)

It could be (and has often been) argued that this song was not a natural continuation of the Hip Hop movement that had been building underground. As early as 1979 the discussion about the difference between commercial ‘sell-out’ / pop-rap and real Hip Hop was prevalent. Because the song was performed by three ‘studio rappers’ who hadn’t been among the ones who pioneered Hip Hop on the Bronx streets, this song was initially dismissed by some.

Be that as it may – “Rappers Delight” was the first (or actually the second … ) Hip Hop song that was released as a single. And despite the controversy surrounding it (also about who actually wrote the lyrics; don’t forget Grandmaster Caz’s uncredited contributions)  – the song became a huge hit around the world. There are many disco influences in the music – the groove was taken from “Good Times” by Chic – but the raps are classic and served as a template for how emceeing could actually be done on a record.

Fun fact: the whole song was recorded in one take.

Grandmaster Flash & The Furious Five - The Message (1982)

Arguably the most important song in Hip Hop history ever. Up till then, Hip Hop lyrics were mostly about fun, parties, and self-aggrandizing. “The Message” was the first song with unabashed commentaries on life and society, and it had a huge influence on many conscious Hip Hop artists who came later. Melle Mel is seen by many as one of the best rappers ever, and Grandmaster Flash was a pioneering DJ. Along with Kool Herc and Afrika Bambaataa, Flash is often considered one of the “Godfathers of Hip Hop”.

Run DMC - Suckers MCs (1983)

Released in 1983, as the B-side to Run DMC’s first single “It’s Like That”, this classic Run DMC cut could still comfortably fit in the Old School category when we only look at the timeline, but in terms of sound it actually does not. This song is a perfect early indicator of the direction Hip Hop was going in. Harder, sparser beats and a new, more aggressive style of rapping. Run DMC is THE group that is responsible for bringing Hip Hop from the Old School to the Golden Age.

LL Cool J - Rock The Bells (1985)

From LL’s groundbreaking debut album Radio. “Rock The Bells” is one of LL Cool J’s signature tracks and a landmark track in Hip Hop history.

Schoolly D - P.S.K. What Does It Mean? (1985)

One of the first songs (or even the very first) that was labeled ‘gangsta rap’ and THE track that inspired Ice T to write 6 N The Morning. Hugely influential, this all-time classic by Philly legend Schoolly D.

Ice T - 6 N The Morning (1986)

Inspired by what arguably was the first ‘gangsta rap’ song – 1985’s “PSK What Does It Mean” by Philly rapper Schoolly D – Ice-T’s “6 N The Morning” is one of the most influential songs in Hip Hop (for better or worse…), as it more or less started gangsta rap. Where most gangsta rappers accomplish nothing but making themselves look like tough-guy posturing, gun-toting idiots, Ice T did it RIGHT. He always combined authenticity with humor, displaying calm confidence without the need to prove anything. Even if most so-called gangsta rap ultimately didn’t do many favors to Hip Hop as a culture, Ice T is one of the few representatives of that particular form of Hip Hop who belongs in the Hip Hop Hall Of Fame without a doubt.

Ultramagnetic MCs - Ego Trippin' (1986)

The original version of one of the centerpieces of Ultramagnetic MCs‘ underrated 1988 masterpiece Critical Beatdown was recorded as early as 1986. A super innovative and absolute classic track.

Beastie Boys - Paul Revere (1986)

The bass-line and reverse beat on this song are just crazy. Co-written by Run DMC and Rick Rubin, the song is a fictional and humorous account of how the Beastie Boys met. Pure genius, “Paul Revere” is Beastie Boys’ best song in a catalog full of classic songs.

Run DMC - Peter Piper (1986)

The opening track to Run DMC‘s magnum opus Raising Hell and a tribute to the skills of the multi-talented Jam Master Jay. On this DJ-favorite, Run and DMC trade lyrics based on nursery rhymes and fairy tales while at the same time paying homage to JMJ’s skills on the turntables.

Boogie Down Productions - South Bronx (1986)

In response to MC Shan’s “The Bridge”, Boogie Down Productions came out HARD with “South Bronx”. It left no room for doubt about where Hip Hop originated nor who reigned supreme. An all-time classic Hip Hop anthem. The song was produced by DJ Scott La Rock, KRS-One and Ultramagnetic MCs’ Ced Gee, and the first single of Boogie Down Productions’ classic debut album Criminal Minded that would be released in 1987.

Public Enemy - Rebel Without A Pause (1987)

“Rebel Without a Pause” was the first song created for and the first single released from Public Enemy‘s masterpiece It Takes a Nation of Millions to Hold Us Back. The song was released in 1987, way before the album came out in the summer of 1988, and it was sort of a bridge between the still somewhat unpolished sounds of Yo! Bum Rush The Show to the Bomb Squad produced perfection on It Takes A Nation.

Eric B & Rakim - I Ain't No Joke (1987)

Rakim immediately sets the perfect tone for the rest of Eric B and Rakim’s debut album with this brilliant opening track to Paid In Full. After dropping their first two classic tracks – “Eric B Is President” and “My Melody” – in 1986, Rakim really raised the bar for lyricists in 1987 with his revolutionary rhyming on Paid In Full – one of the top albums in all of Hip Hop’s history.

Just Ice - Going Way Back (1987)

This track by Just-Ice (with the help of a young KRS-One) deals with the origins of Hip Hop in the Bronx and the rest of New York. Just-Ice names everyone that matters – a real Hip Hop history lesson.

Audio Two - Top Billin' (1987)

Talk about a classic Hip Hop song. The brilliant reworking of the “Impeach The President” beat is simply unbeatable. Even if they never made any other real noteworthy music, Audio Two will forever be remembered because of this monumental track – released in 1987 as the lead single for their otherwise disappointing 1988 album What More Can I Say?

Biz Markie - Vapors (1988)

The lead single from the late Biz Markie‘s full-length debut album Goin’ Off. In full story-telling mode, Biz shows us how people’s behavior towards you changes after you become successful. ”Vapors” is a monumental 1980s Hip Hop song.

Big Daddy Kane - Set It Off (1988)

The ultimate example of Big Daddy Kane’s rapping prowess and lyrical skill. Pure, unadulterated Hip Hop – it doesn’t get any better than this. With “Raw”, “Ain’t No Half-Steppin΅ nad “Long Live The Kane”, one of the stand-out tracks of the all-around masterful Marley Marl-produced debut album Long Live The Kane.

EPMD - You Gots To Chill (1988)

“You Gots To Chill” is the quintessential EPMD song. It introduced the world to the laidback funk-laced Hip Hop of EPMD – and is just as timeless as Strictly Business, the classic album it came from.

MC Lyte - Paper Thin (1988)

An emcee who can spit with the best of them, male or female. MC Lyte‘s debut album still is a classic piece of work, that belongs in any Hip Hop fan’s collection. “Paper Thin” is the now-classic cut with which Lyte made her mark.

Public Enemy - Black Steel In The Hour Of Chaos (1988)

This is one of the most impactful songs Public Enemy ever did, and that is saying something. A powerful story of a jailbreak, directed at the US government and its prison system. Hard-hitting lyrics, perfect instrumental – this is Public Enemy at its best.

Stetsasonic - Talkin' All That Jazz (1988)

This underappreciated song is a response to critics of (sampling in) Hip Hop. The stand-out track from Stetsasonic’s solid second album In Full Gear.

Eric B & Rakim - Follow The Leader (1988)

Five minutes of lyrical perfection. Together with “Lyrics of Fury”, perhaps one of the best examples of how advanced Rakim was with his lyricism. Listen to it and then listen to it again and let it sink in. Rakim will take the listener on a metaphorical trip into outer-space and then back into the listeners head – a lyrical masterpiece.

Marley Marl ft Craig G, Master Ace, Big Daddy Kane & Kool G Rap - The Symphony (1988)

Marley Marl’s “The Symphony” is THE ultimate posse cut, the standard by which all other posse cuts are measured. Marley Marl’s beat brilliantly interpolates Otis Redding’s Hard to Handle, Masta Ace and Craig G warm things up nicely, and Kool G Rap and Big Daddy Kane kill it with classic verses.

Boogie Down Productions - My Philosophy (1988)

This track was so far ahead of its time, Hip  Hop still hasn’t caught up yet. Filled with Hip Hop Quotables, “My Philosophy” addresses the commercialization of Hip Hop and the rise of wack and fake rappers. Over 30 years old and as relevant today as ever.

Rob Base & DJ E-Z Rock - It Takes Two (1988)

This platinum-selling single arguably is THE biggest mainstream-friendly Hip Hop song of the 1980s. Massive crossover appeal and a party favorite to this day.

N.W.A - Straight Outta Compton (1988)

N.W.A’s Straight Outta Compton album was a game-changer; for better or for worse. One of the first real Gangsta Rap albums, going multi-platinum without any radio play. It influenced and changed the direction of Hip Hop, producing countless clones for decades to come. The difference between all the clones and this album is the originality and authenticity of Straight Outta Compton; combined with the revolutionary & flawless production of Dr Dre and the raw energy & at the time shocking lyrical imagery of Ice Cube, MC Ren & Eazy E. The album is a super classic and this title track is the perfect opening salvo.

Slick Rick - Children's Story (1988)

After he made his imprint on the scene in 1985 on Doug e Fresh’s classic songs “The Show” and “La Di Da Di”, Slick Rick released his nearly flawless debut album The Great Adventures Of Slick Rick in 1988. Slick Rick’s superior storytelling abilities, combined with his humor and typical rap style shine on the whole album, this is the best song.

Ice T - Colors (1988)

The powerful title track of the classic 1988 movie “Colors”, and one of Ice-T’s best tracks.

Eric B & Rakim - Microphone Fiend (1988)

Strangely the single release of this track wasn’t a huge success in 1988, but since then this track has come to be recognized not only as the quintessential Eric B & Rakim song but as one of Hip Hop’s biggest songs as well.

N.W.A - F*** Tha Police (1988)

One of the most controversial songs in Hip Hop ever? The sad thing is that in the more than 30 years since this song was recorded nothing has changed…

De La Soul - Buddy ft. Jungle Brothers & Q-Tip (1989)

“Buddy” is the third single from De La Soul’s classic debut album 3 Feet High and Rising. Great vibe and great lyrics – humorous and full of double entendres. Some people prefer the remix and video version, we are sticking with the original version.

Special Ed - I Got It Made (1989)

Special Ed’s signature track. Over an epic beat laid down by Howie Tee, a young Special Ed (15 years old at the time!) drops some of the best and most humorous braggadocious rhymes ever. All these guys today rapping about how much money they make should listen to this song…

Queen Latifah ft Monie Love - Ladies First (1989)

Empowering content AND dope flows by both Queen Latifah and Monie Love – this feministic anthem is an all-time Hip Hop classic.

Beastie Boys - Shake Your Rump (1989)

Everything that makes Paul’s Boutique so brilliant comes together on this track. The album performed commercially disappointing upon release (people were probably expecting more “Fight For Your Right” style frat-rap), but Paul’s Boutique would eventually universally be recognized as the creative and innovative masterpiece that it is.

Public Enemy - Fight The Power (1989)

Arguably Public Enemy’s best-known track, the musical theme for Spike Lee’s classic movie Do The Right Thing is universally regarded as one of the best songs of all time. We agree.

LL Cool J - Mama Said Knock You Out (1990)

The Marley Marl produced title track of LL Cool J‘s fourth album, Mama Said Knock You Out, showed LL in top form. 22 years old at the time – and already a Hip Hop veteran, LL Cool J felt it was necessary to knock out all critics who said he fell off with his third album, Walking With A Panther. The song was produced by Marley Marl and uses samples from James Brown’s “Funky Drummer,” the Chicago Gangsters’ “Gangster Boogie,” Sly & The Family Stone’s “Trip to Your Heart” the drum break from Digital Underground’s “The Humpty Dance”, and LL Cool J’s own “Rock the Bells”.

Boogie Down Productions - Love's Gonna Getcha (Material Love) (1990)

The perfect example of storytelling and conveying a message through music. The brilliant video that goes with it makes this thought-provoking song even stronger.

Kool G Rap & DJ Polo - Streets Of New York (1990)

The first single from Kool G Rap & DJ Polo’s 1990 album Wanted: Dead or Alive, has G Rap rapping about the social issues in New York City’s ghettos, such as alcoholism, domestic violence, drug abuse, gambling addiction, gun violence, homelessness, police corruption, poverty and prostitution, over piano and saxophone samples of the Fatback Band’s “Gotta Learn How To Dance”

Too Short - The Ghetto (1990)

A departure from his trademark ‘dirty raps’, this radio-friendly social commentary is one of Too Short‘s biggest hits (selling close to 3 million units).

A Tribe Called Quest - Check The Rhime (1991)

The lead song of The Low End Theory – one of Hip Hop’s most celebrated albums ever – shines because of the back-and-forth synergy between Q-Tip and Phife, who bounce their lines off each other effortlessly and to perfection. The ultimate ATCQ track?

Black Sheep - The Choice is Yours (Revisited) (1991)

“The Choice Is Yours” is the second single taken from Black Sheep‘s classic debut A Wolf In Sheep’s Clothing and an all-time party favorite. The original version is great, the revisited version is even better.

Naughty By Nature - O.P.P. (1991)

Restyling themselves Naughty By Nature after a not bad but unsuccessful debut album under the name “The New Style”, NBN became a major commercial success. “O.P.P.” is probably their best-known track in a long string of hits.

Geto Boys - Mind Playing Tricks On Me (1991)

Geto Boys’ signature and best track. Check Brian Coleman’s Check the Technique: Liner Notes for Hip-Hop Junkies for the story behind “Mind Playing Tricks On Me“.

Tribe Called Quest - Scenario ft. Leaders of the New School (1991)

Probably one of the best known and most popular posse cuts in the history of Hip Hop. With his legendary bars on this track, Busta Rhymes pretty much laid the foundation for his solo career and stardom (and the end of The Leaders Of The New School). Infectious and catchy, this song closes out the already perfect Low End Theory album on a high note.

Cypress Hill - How I Could Just Kill A Man (1991)

Arguably the best track from Cypress Hill’s highly original debut album. DJ Muggs’ funk-laced and bass-heavy production filled with creative sampling, combined with the unique voices of emcees Sen Dog and especially B-Real, created Cypress Hill’s instantly recognizable, signature sound.

Pete Rock & CL Smooth - They Reminisce Over You (T.R.O.Y.) (1992)

“They Reminisce Over You (T.R.O.Y.)” was inspired by the death of Pete Rock & CL Smooth’s close friend Troy Dixon (better known as “Trouble” T. Roy of Heavy D & the Boyz) in 1990. The song was the lead single off their monumental debut album Mecca And The Soul Brother and is now widely regarded as one of the best Hip Hop songs of all time.

Ice Cube - It Was A Good Day (1992)

This feel-good hood anthem is Ice Cube’s best song, a timeless and essential piece of Hip Hop.

House Of Pain - Jump Around (1992)

THE ultimate party anthem in Hip Hop? This timeless DJ Muggs-produced House Of Pain classic is certainly up there with the best of them.

The Pharcyde - Passin' Me By (1992)

In an era when gangsta rap was starting to dominate West Coast Hip Hop, these guys didn’t feel the need for gangster posturing and weren’t afraid to show their humorous & vulnerable sides. “Passin’ Me By” is one of the big tracks off their epic debut album Bizarre Ride II The Pharcyde and an undisputed Hip Hop classic.

Dr. Dre ft Snoop Doggy Dogg - Nuthin' But A G Thang (1992)

A hugely influential & timeless classic, this ‘G-Funk’ track and lead single off Dr. Dre’s seminal The Chronic ushered in a new era in Hip Hop. It established West Coast dominance in rap, and it was the breakthrough moment for Dr. Dre’s young protégé Snoop Doggy Dogg.

The Goats - Typical American (1992)

“Typical American” is the lead track off The Goats’ debut album Tricks Of The Shade – a highly original concept album, ahead of its time. An underground classic by this forgotten Philadelphia alternative Hip Hop trio.

Wu-Tang Clan - Protect Ya Neck (1993)

The debut single from Wu-Tang Clan’s classic first album Enter the Wu-Tang (36 Chambers) was a gamechanger. It features verses from eight of the original nine Wu-Tang members. It was an incredible introduction of a new supergroup to the Hip Hop scene and a perfect prelude of equally brilliant things to come.

2Pac - Keep Ya Head Up (1993)

Being a central part of the gangsta rap culture, 2 Pac was no stranger to misogyny in his lyrics. He had another side too, however. This uplifting song is all about the betterment of women. The interpolation of The Five Stairsteps’ brilliant “O-o-h Child” makes for a more than pleasing instrumental too.

A Tribe Called Quest - Electric Relaxation (1993)

Not just one of ATCQ’s best tracks, this ode to women is one of the best tracks in Hip Hop. A masterpiece.

KRS One - Sound Of The Police (1993)

As relevant today as it was three decades ago, in this song KRS-One addresses police brutality specifically directed at Black people, cleverly linking the days of slavery to the way police acts in these modern times. Poignant, powerful, and sadly still relevant. One of the many excellent tracks on KRS’s debut album under his own name.

Snoop Doggy Dogg - Gin & Juice (1993)

“Gin & Juice” is the second single by Snoop Doggy Dogg from his debut album Doggystyle, and one of Snoop’s signature songs. Expectations for Snoop’s debut album were sky-high after his performances on Dr Dre’s The Chronic, and with Doggystyle Snoop (and Dre) delivered, and then some.

Wu Tang Clan - C.R.E.A.M. (1993)

The final single from Wu-Tang Clan’s monumental debut album Enter The Wu-Tang (36 Chambers). C.R.E.A.M. offers a haunting lesson in street economics; with excellent verses from Raekwon and Inspectah Deck, and with Method Man‘s unforgettable hook.

Souls Of Mischief - '93 Til Infinity (1993)

Souls Of Mischief‘s lead track off their slept on 1993 debut album with the same title is an all-time Hip Hop classic.

OutKast - Players Ball (1993)

The pimped-out classic that started it all, the first single of Southernplayalisticadillacmuzik which would be released in 1994. An incredibly important and influential song, as it was OutKast’s introduction to the world and the kick-off of a decade with brilliant OutKast music. A staple for Hip Hop, not just for the South.

Jeru The Damaja - Come Clean (1993)

“Come Clean” is a 1993 DJ Premier-produced song by Jeru the Damaja from his brilliant 1994 debut album The Sun Rises in the East. The song (and the rest of the album) feature some of the best production work DJ Premier has ever done, this is one of his most recognizable beats.

Warren G ft Nate Dogg - Regulate (1994)

“Regulate” is the worldwide smash hit by Warren G and Nate Dogg. Released in the summer of 1994, the track appears on the soundtrack to the film Above the Rim and later Warren G.’s album Regulate…G Funk Era. One of those timeless tracks that still gets played today.

O.C. - Time's Up (1994)

O.C.‘s “Time’s Up” from his underrated 1994 album Word…Life was a scathing accusation, pointed at studio gangsters and thug-posturers who were flooding the Hip Hop scene at the time.

Nas - N.Y. State Of Mind (1994)

The quintessential Nas track and one of Hip Hop’s best songs ever, bar none. A classic narrative of life on the NYC streets, this is one of the many classics Nas’ partnership with DJ Premier would yield and just maybe the biggest of them all.

Common - I Used To Love H.E.R. (1994)

In this super classic track, Common cleverly describes what appears to be his changing feelings for a girl, but what turns out to be his ever-evolving relationship with Hip Hop. Truly a landmark recording and the centerpiece of one of the best albums in one of Hip Hop’s best years.

The Notorious B.I.G. - Juicy (1994)

The first single from Notorious B.I.G.‘s monumental debut album Ready To Die and an unbelievable critical and commercial success. This classic Biggie joint is an all-time classic not just because of its universal appeal, but because of its essentially positive vibe and emotion.

Gang Starr - Mass Appeal (1994)

Gang Starr always had that straight-up, real hardcore Hip Hop. In this classic joint from their fourth album Hard To Earn, they address sell-out artists who are willing to compromise their sound and themselves for chart success. The quintessential Gang Starr track.

Luniz - I Got 5 On It (1995)

“I Got 5 On It” is a mega-hit by Oakland duo Luniz. It was released in May 1995 as the lead single from their debut album, Operation Stackola, and is one of those rare songs that has stayed in rotation worldwide to this day. “I Got 5 On It” brilliantly samples Club Nouveau’s “Why You Treat Me So Bad” (1987), Kool and the Gang’s “Jungle Boogie” (1973) and Audio Two’s “Top Billin’” (1987).

KRS One - MCs Act Like They Don't Know (1995)

The perfect symbiosis of the KRS-One – DJ Premier collaboration. Over Premo’s masterpiece instrumental, interpolating Kurtis Blow’s classic “The Breaks”, KRS once again lets other rappers know what’s the deal. The lesson to be learned here: you’re not a real emcee if you can not rock a crowd. No one is better suited to make that claim than one of the best live performers Hip Hop has ever seen.

Mobb Deep - Shook Ones II (1995)

Classic Mobb Deep rhymes over a signature sinister Havoc beat – this song is not just Mobb Deep’s best, but one the very best in the history of Hip Hop. THE centerpiece of the all-around epic album The Infamous, which played a big part in the ‘renaissance’ of East Coast Hip Hop.

The Pharcyde - Runnin' (1995)

This Pharcyde track was produced by the late, great J Dilla – resulting in a timeless masterpiece. “Runnin’” was released as the first single from The Pharcyde’s underrated second album Labcabincalifornia in 1995, and remains one of Pharcyde’s most recognizable and most popular songs.

Coolio - Gangsta's Paradise (1995)

“Gangsta’s Paradise” was 1995 biggest selling single – in any musical genre – and even one of the biggest selling singles ever. The huge mainstream success of this song pretty much ended Coolio’s Hip Hop career, but this song has to be recognized as a classic (even if you’ve heard it a thousand times too many…).

The Roots - What They Do (1996)

Taken from The Roots‘ classic third album Illadelph Halflife, this brilliant video (with its subtitles) shows a sense of humor perfectly matches up to the song’s message. Like De La Soul‘s 1993 “Ego Trippin’ Pt 2“, the song and the video sarcastically critique the ‘bling-bling’ cliches that already started dominating Hip Hop videos back in the mid-1990s. Classic material, with a message as relevant today as it was over 25 years ago.

Ras Kass - Nature Of The Threat (1996)

One of the most controversial Hip Hop songs of all time? This trip through human history touches on religion, homosexuality, Afrocentrism, racism, government corruption, and more – all in a stunning display of lyrical mastery by one of the most underrated emcees ever.

Ghostface Killah - All That I Got Is You (1996)

In this beautiful autobiographical song, Ghost tells the story of his impoverished childhood and the struggles growing up. He raps about how he grew up in a three-bedroom apartment without his father who left him at the age of six. Growing up poor he experienced hard living conditions like “Pluckin’ roaches out the cereal box. ”

The album version featured Mary J Blige, the video version regular Wu-Tang collaborator Tekitha. “All That I Got Is You” is another absolute Hip Hop classic.

2Pac - Dear Mama (1996)

“Dear Mama” is an emotional tribute to 2Pac’s mother and one of his most celebrated and most famous songs.

Bone Thugs N Harmony - Crossroads (1996)

Released as a single in 1996, and in this version not appearing on their album 1995 E. 1999 Eternal album, “Tha Crossroads” is the biggest selling single and Grammy-winning song by Bone Thugs-N-Harmony. This remake of the original “Crossroads” was done after the death of BTNH mentor Eazy E, which makes this timeless dedication to deceased loved ones all the more heartfelt.

The Fugees - Ready Or Not (1996)

A great commercial as well as a critical success, The Score was a massive improvement on The Fugees‘ enjoyable but uneven Blunted On Reality debut album. The Score is a timeless and flawless masterpiece and “Ready Or Not” is but one of the many outstanding tracks on the album, a rather brilliant reworking of the 1968 Delfonics classic.

Puff Daddy ft. The Lox, Lil’ Kim & The Notorious B.I.G. - It’s All About The Benjamins (Remix) (1997)

There’s a lot to be said about Puff Daddy and the negative impact his marketing machine had on Hip Hop in general, but there’s no denying this is a banger. Epic line-up, and a classic instrumental with a dope beat switch from Biggie’s verse. This is Puff Daddy’s best song.

Camp Lo - Luchini (a.k.a. This Is It) (1997)

“Luchini (This Is It)” is the lead single released from Camp Lo‘s underrated 1997 debut album, Uptown Saturday Night. Great vibe, great song.

Wu Tang Clan - Triumph (1997)

This monumental song features all nine original members of the Wu-Tang Clan, plus Cappadonna. Straight bars, no hook – this is an epic track with Inspectah Deck laying down one of the most lauded opening verses is Hip Hop ever.

Black Star ft Common - Respiration (1998)

“Respiration” is a track off the Mos Def and Talib Kweli are Black Star album, with three brilliant verses from Mos Def, Talib Kweli, and guest emcee Common, putting three of the most renowned poets in the genre on the same song and giving rap fans a sneak preview for the careers of all three artists. The song unfolds as a vignette of short stories, each verse a snapshot of city life, starting in Mos Def and Kweli’s perception of Brooklyn, and ending in Common’s hometown of Chicago. Some say “Respiration” is the most perfect rap song ever written. What do you think?

Pharoahe Monch - Simon Says (1999)

“Simon Says”, the first single of Pharoahe Monch’s solo debut Internal Affairs was released in 1999. “Simon Says” became a hit single, peaking at No. 97 on the Billboard Hot 100. Despite its success, the song caused controversy when Monch was later sued for the song’s use of a sample from Akira Ifukube’s Gojira Tai Mosura in the hook.

Mos Def - Mathematics (1999)

From his classic solo debut album Black On Both Sides, this timeless DJ Premier-produced banger is one of Mos Def’s signature cuts. Fun fact: this is one of Premier’s own favorite beats.

OutKast - B.O.B. (2000)

“B.O.B.” is a crazy track, with spitfire rhymes and a head spinning beat – as unconventional as it is brilliant. The epitome of OutKast’s unique approach to Hip Hop.

Eminem - Stan (2000)

This bone-chilling tale of an obsessed fan is the centerpiece of the all-around masterpiece The Marshall Matters LP, and one of Eminem’s biggest singles in a catalog full of classics.

Mos Def, Pharoahe Monch & Nate Dogg - Oh No (2000)

Oh No is a classic track from Lyricist Lounge 2 with A+ verses from Mos Def and Pharoahe Monch and with Nate Dogg on the hook. An East Coast – West Coast collaboration you can’t go wrong with.

Immortal Technique - Dance With The Devil (2001)

“Dance With The Devil” is an extremely descriptive metaphor for the degradation of values and culture, and the consequences of that degradation for individuals and society as a whole. An incredibly powerful and hard-hitting song with a clear message: don’t ‘dance with the devil’. Think about it.

J-Live - Braggin Writes (2001)

J-Live is one the most underappreciated emcees of all time and his debut album The Best Part is one of the most underappreciated Hip Hop albums ever. “Braggin’ Writes” is one of the incredible tracks on this album.

Eminem - Lose Yourself (2002)

The theme song from Eminem’s semi-biographical movie 8 Mile not only is Eminem’s best single, but also one of the best (and most successful) in the history of Hip Hop.

Mr. Lif - Return Of The B-Boy (2002)

“Return Of The B-Boy” (in which Mr. Lif is resurrected as a Hip Hop messiah), is the epic 8-minute centerpiece of Mr. Lif’s masterpiece cult classic I Phantom.

Missy Elliott - Work It (2002)

Missy’s “Work It” is a perfect throwback jam that brilliantly incorporates Run-DMC’s “Peter Piper,” Rock Master Scott & The Dynamic Three’s “Request Line” and Blondie’s “Heart of Glass.”

Jay-Z - 99 Problems (2003)

Rick Rubin brings the old-school rock-driven beats he used to build the careers of LL Cool J and Beastie Boys on for this third single from Jay-Z’s The Black Album. The hook “I got 99 problems but a bitch ain’t one” is taken from the Ice-T single “99 Problems” from the album Home Invasion (1993). The second verse is a fictional account of racial profiling by the police, but it is based on a true story.

50 Cent - In Da Club (2003)

50 Cent’s breakthrough is one of the most recognizable songs in Hip Hop ever, thanks to Dr. Dre’s classic instrumental.

Madvillain - All Caps (2004)

The best track on Madvillainy, one of the best Hip Hop albums of all time. In his trademark abstract way, MF DOOM conveys a simple message: always remember it’s MF DOOM, not MF Doom. All Caps.

The Game - Hate It Or Love It (2005)

The Game embodies his hometown’s underdog spirit in “Hate It Or Love It”, which achieved commercial success worldwide when it was released as a single in January 2005. While The Game was riding high on the strength of two massive singles, “West Side Story” and “How We Do”, it was “Hate It Or Love It” that showed The Game at his apex. It was the moment he captured everyone’s attention with his tales of the hood. With razor-sharp rhymes, The Game and 50 Cent construct a rags-to-riches story, rapping about where they came from and their struggles growing up in rough, poverty-stricken neighborhoods. A classic Hip Hop tune and The Game’s biggest hit to date.

Common - The Corner (2005)

“The Corner” is the second single released by rapper Common from his sixth album, Be. It features a chorus and production by Kanye West as well as spoken word lyrics by The Last Poets. The song’s lyrics deal with street corners in poor neighborhoods. The song’s beat contains samples from “You Make the Sun Shine” by The Temprees and “What It Is” by The Temptations.

Percee P - Throwback Rap Attack (2007)

Whenever we compose a list like this one, we need little excuse to include Percee P. He is one of the most underrated lyricists ever, and he deserves the spotlight. “Throwback Rap Attack” is the centerpiece of his first and only album Perseverance, which was entirely produced by Madlib. This song is an exhibition of superior lyricism, supported by a dope driving Madlib beat.

UGK - International Players Anthem ft. OutKast (2007)

“International Players Anthem” is an iconic collaboration between Southern titans UGK and OutKast, with a stand-out spoken word opening from Andre 3000, and dope verses from Bun B, Pimp C, and Big Boi over a butter-smooth instrumental.

Nas & Damien Marley - Patience (2010)

Distant Relatives is a collaborative studio album by Nas and Jamaican Reggae vocalist Damian Marley, the legendary Bob Marley’s youngest son. Distant Relatives is a seamless fusion of Hip Hop, Reggae, Dancehall, and African musical elements, with uplifting afro-centric vocals about freedom, family, spirituality, and ancestry. At 65 minutes, Distant Relatives offers both quantity and quality – all killer, no filler. Distant Relatives is aging really well and sounds as timely and timeless today as it did the day it was released. Maybe because this is a collaboration or because it’s a fusion of musical styles and not 100% Hip Hop, this genre-blending gem is often forgotten when Nas’ work is discussed. The empowering “Patience” is the absolute stand-out track on Distant Relatives.

Kanye West - Monster (2010)

“Monster” is the best track on Kanye West’s best album, and “Monster” is one of the best posse cuts in Hip Hop too. Kanye comes with clever bars, Jay Z with a dope braggadocious verse, but it is Nicki Minaj who steals this show, going all out with a killer performance.

Lupe Fiasco - Mural (2015)

This is the only post-2010 song on this list, not because there hasn’t been any good Hip Hop since then (on the contrary, in fact), but songs need to ‘marinate’ for a decade or more to be sure they can be counted among the best of all time. Lupe Fiasco’s “Mural” is an exception – this was an instant classic, the best Hip Hop song of the decade. “Mural” appears on Lupe Fiasco’s fifth studio album Tetsuo & Youth. The song title draws parallels to an actual mural, given its length and the permanent impact this song will have. Almost nine minutes long with no hooks, the song contains 785 unique words and is a masterclass in lyricism.

Stream 100 Of The Best Hip Hop Songs Of All Time @ Spotify