Top 100 old-school hip-hop songs.

I’m a huge fan of old-school hip-hop music and have wanted for some time to put down some kind of ranking of my favorite songs from that era. I’ve been working on this post since late February, but it’s finally done now that the draft crush and our summer east coast swing are over. It started out as a top 40, then a top 50, then 75, after which I figured I’d just push it to 100.

This is list is entirely my opinion, and maybe 90% of it is just about how much I personally like the songs, with the other 10% reserved for the song’s influence or importance in hip-hop history. And it’s about how the songs have held up over time, not which songs I liked when they first came out or how they fared on the charts.

I’ve limited the list to songs released, either as singles or on albums, prior to 1996. That cutoff means no Jay-Z or Eminem and virtually no Nas or Outkast, to pick a few examples, but with one exception (a song recorded before the deadline but released afterwards) I stuck to the deadline for all tracks. Enjoy.

100. “Check Yo Self” – Ice Cube

Samples an early hip-hop classic, “The Message,” that was already dated before the 1980s ended, with guest vocals by Das Efx on the chorus. Ice Cube’s lyrics often led to controversy – something I doubt he minded since even bad publicity sells records – but I don’t think the anti-gay lines in this song would fly today like they did in the early ’90s. (Corrected on 7/7 – added this song to remove an ineligible song from higher on the list.)

99. “Gotta Get Mine” – MC Breed featuring 2Pac

No disrespect to MC Breed, who died of kidney failure when he was 38, but 2Pac is the main attraction here, one of five appearances for him on this list. Snoop Dogg references this song at the beginning of the second verse of “Gin and Juice.”

98. “Black Steel in the Hour of Chaos” – Public Enemy

Perhaps the greatest opening lines in the history of hip hop: “I got a letter from the government/The other day/I opened, and read it/It said they were suckers/They wanted me for the army or whatever/Picture me givin’ a damn, I said never.”

97. “Fuck tha Police” – NWA

I always wondered if this was mostly a publicity stunt (that worked). I’m not doubting the anti-police sentiment behind it, but the title is so clownishly incendiary that it was a lock to get negative attention in the mainstream media, which would sell more records. In that sense, it’s brilliant. The song was surpassed by its own marketing.

96. “Walk This Way” – Run-DMC

More here for its importance than the quality of the rhymes. It’s hard to express their mainstream influence unless you lived through it; they had street credibility but were inoffensive enough to be marketed to white, suburban audiences. Unfortunately most of their catalog sounded dated within a decade of its release.

95. “The Humpty Dance” – Digital Underground

It was written as a novelty, it became a hit as a novelty, and like most novelty hits it wrecked the artist’s career when they couldn’t produce another song just like it. That’s too bad, because they were one of the most interesting acts of the late ’80s/early ’90s, but between this and the forgettable “Kiss You Back” their run was good for about an album and a half.

94. “Holy Intellect” – Poor Righteous Teachers

No shot of crossover success for a group that rapped almost entirely about their Islamic faith, but the speed and quality of the rhyming here is remarkable.

93. “Ain’t Sayin Nothin” – Divine Styler

Remember House of Pain’s line in “On Point” about how “I used to rap with the Divine Styler?” He was actually a hell of an MC, and just about anything from that first album is worth listening to. His second disc was a wildly experimental jazz/rap/ambient fusion that was way ahead of its time, and he took a long break before coming back with a late-90s disc after his conversion to Islam that had one standout track, “Make It Plain.”

92. “Chief Rocka” – Lords of the Underground

These guys came along a little too late, when the west coast scene was paramount and east coast groups had a harder time breaking through even if their sound was more overtly commercial.

91. “Express Yourself” – NWA

I love hearing Dr. Dre rap about how marijuana causes “brain damage/and brain damage on the mike can’t manage” about five years before creating his magnum opus and naming it after the drug.

90. “True Fu-Schnick” – Fu-Schnickens

Total novelty act, but I admit, I love hearing how quickly Chip-Fu can drop rhymes. For a one-trick act, it’s a good trick.

89. “Rock Box” – Run-DMC

Jam Master Jay really held this group together, as neither Run nor DMC were especially gifted rappers.

88. “Rock the Bells” – LL Cool J

The low production values on a lot of early hip-hop classics, including Audio Two’s “Top Billin” and BDP’s “Criminal Minded,” makes them relatively hard to listen to today. This one survives because of the strength and ferocity of LL’s rhymes, which soon gave way to the Smoove B-like persona that dominated his later work (and set him up well for a career in Hollywood).

87. “Hot Sex” – A Tribe Called Quest

“I heard she likes a two-on-one like my man John Ritter.” Never a big fan of Phife’s – Q-Tip carried all of the weight for the Tribe – but that’s among his best lines.

86. “Eric B. is President” – Eric B. & Rakim

“I came in the door/I said it before/I never let the mike magnetize me no more.” There’s something about a debut single that makes an announcement that the artist has arrived, and the entire genre is about to get a swift kick in the ass. Rap’s greatest MC with one of its greatest DJs combine for a track that remains memorable even though it sounds like it was recorded on a handheld cassette recorder.

85. “Ain’t No Half Steppin” – Big Daddy Kane

A poor cousin to his two real standout tracks, which are much further up the list.

84. “A Roller Skating Jam Named Saturday” – De La Soul

Speaking of self-immolation, why did De La Soul fight to shed the alternative-rap label that brought them so much success? I never understand artists trying to be less commercial. If you want to make less commercial music for artistic reasons, but deliberately flipping off your audience by creating less interesting content is insane.

83. “Funkin’ Lesson” – X-Clan

The Afro-centric rap movement died a quick and probably justified death, but these guys were pioneers in their heavy use of P-Funk shortly before that became the foundation for most west coast rap and the “G-Funk” movement.

82. “Vapors” – Biz Markie

Biz Markie was a legitimate rapper before the novelty hit I won’t even deign to name here, and a pretty good beat-boxer as well.

81. “The Formula” – The D.O.C.

The DOC appears on this list three times from his incredible and somewhat overlooked debut album, after which a bad car accident wrecked his voice and ended his hip hop career. The whole disc stands up well against The Chronic and Doggystyle even though it came out three years earlier, with similarly funky beats, clever wordplay, and plenty of weapon-filled boasting.

80. “Rump Shaker” – Wreckx-n-Effect

Not Teddy Riley’s best track – that would be Blackstreet’s “No Diggity” – but a worthwhile novelty hit with the raunchiest use of state names in rap history.

79. “Nuttin But Love” – Heavy D

The Overweight Lover’s stuff hasn’t aged all that well either, although I admit a certain guilty pleasure in “We Got Our Own Thang;” this track has his best rhyming by far and one of the most memorable lines in any video from the 1990s – “Yo, that’s that Noxzema girl!” Heavy D was born in Jamaica but reggae was always a background note in his music before this album, where you could hear its influence more strongly.

78. “Quik is the Name” – DJ Quik

I remember seeing DJ Quik appear on the Billboard top 200 albums chart and being completely confused. How the hell did someone I’d never heard of end up with a top 20 album out of nowhere? I hadn’t heard of him because west coast rap got very little airplay or even word-of-mouth on the east coast at that point; his success was regional at a time when rap was never heard on pop radio.

77. “On Fire” – Stetsasonic

“And rock and roll could never hip hop like this.” The line that spawned an alternative classic from the 1990s by Handsome Boy Modeling School, one-half of which was Stetsasonic mastermind Prince Paul.

76. “Welcome to the Terrordome” – Public Enemy

This song seemed like a major disappointment when it came out, because it had all of the urgency of It Takes a Nation of Millions… without the same caliber of lyrics or music; it felt like PE had rushed the track (and album) out to capitalize on the late-blooming success of their previous album. But today the urgency of the track stands out, and it marked one of Chuck D’s last great lyrical achievements before the group faded into the hip-hop background.

75. “Nappy Heads” – Fugees

Did any rap act every do less with more than the Fugees? The talent involved was enormous, and yet their biggest hit was a straight-up soul remake of an adult contemporary classic. Lauryn Hill had her one amazing solo album before releasing Lauryn Hill: Unhinged, and Wyclef has had a strong solo career, but as the Fugees one plus one plus one (Pras) equaled something less than three.

74. “My Philosophy” – Boogie Down Productions

A six-minute rant by the literate if rather preachy KRS-ONE. I’ve wondered how BDP’s legacy would differ if DJ Scott La Rock had lived; would it be greater because their music would have been better, or would it have suffered because so much of their fame came from that tragedy?

73. “Hip Hop Hooray” – Naughty by Nature

Naughty by Nature pretended to be hardcore, but most of their singles were straight-up pop songs, designed to sell lots of records. I have no problem with that, but just be what you are, right?

72. “Check the Rhime” – A Tribe Called Quest

I’m going to run out of things to say about the Tribe soon enough.

71. “Droppin’ Rhymes On Drums” – Def Jef

Def Jef was better known as a producer and as the rapper behind the disgustingly misogynistic song “Give It Here,” but this track is stronger all around – better rhymes, faster pinpoint delivery, and intense backing music that makes the whole thing sound like a sprint.

70. “Do the Right Thing” – Redhead Kingpin & the FBI

Recognizable within a second for that opening sample, and led by Redhead Kingpin’s laconic delivery that eventually became the hallmark of Snoop Dogg, but one thing bothered me about this song: He never actually says what the right thing is.

69. “Flavor for the Non-Believes” – Mobb Deep

I didn’t realize how successful this duo had been until I researched them for this list – their best track for me came from their original demo, although I think most people would argue for “Peer Pressure” or the crude “Hit It From the Back.”

68. “Don’t Sweat the Technique” – Eric B. & Rakim

There’s something slightly off about this track; Eric B. dropped some of the fattest beats of his career, only to have Rakim deliver what was for him a subpar performance, with slower, less inspired rhymes, which in hindsight was a bad sign for his post-breakup future. “I made my debut in ’86” rapped at half-speed is just cringeworthy.

67. “O.P.P.” – Naughty by Nature

Ignore, for a moment, that this too was aimed squarely at mainstream pop audiences. The song is full of clever wordplay, from the disguising of the two p-words to “throw that skeleton bone right in the closet door” to “you’re now down with a discount” to the inscrutable “look you to the stair and to the stair window.” And it’s backed up by a sample from the Jackson 5. You can’t like old-school hip hop and dislike this song.

66. “What’s My Name” – Snoop Doggy Dogg

Yeah, Snoop, we got it. You only say your name twelve times in every song you record.

65. “U Don’t Hear Me Tho’” – Rodney-O and Joe Cooley

Released four or five years too soon, this was G-Funk before the term existed, layered on heavy samples of P-Funk music with the same gangster ethos that Dr. Dre would later mine for great profits. The lines “Time for me to kick another fly funky verse/and if I die, put a soundsystem in my hearse” is one of my favorite from the entire era.

64. “Let the Words Flow (a.k.a. The Power)” – Chill Rob G

This is the song that Snap! ripped off for their own version of “The Power,” featuring slightly better production and markedly inferior rapping by something called Turbo B. (Their original version contained Chill Rob G’s vocals, but he threatened to sue and they had to re-record them.) Hip hop has seen plenty of tracks saying “everyone else’s rhymes suck,” but this is one of the few that seems to actually argue that everyone else should get better, rather than just boosting the ego of the rapper making the statements.

63. “Southernplayalisticadillacmuzik” – Outkast

One of the few hip-hop acts to hold my attention after the end of the Golden Era, Outkast just sneaked under the wire here with their first album, which came completely out of left field into a genre dominated by G-Funk at the time and that had never produced anything like the inventive music on their debut, a funky, sludgy sound that seemed to take the humidity of Atlanta summers and put it on wax.

62. “Shake Your Rump” – Beastie Boys

The second-best track on one of the greatest albums in the histories of hip-hop and of alternative music (Corrected 7/7).

61. “Passin’ Me By” – The Pharcyde

The record-buying public largely passed these guys by, a true alternative-rap act who didn’t have the commercial sound for major record sales but showed strong rhyming skills and a pervasive sense that they were having a great time laying down tracks.

60. “Changes” – 2Pac

Possibly cheating – this song was recorded in 1992, but wasn’t released as a single until 1998. But it belongs here, as it’s clearly of this era and genre and features some of 2Pac’s most intelligent and thoughtful lyrics. Discussing the plight of the black American underclass in rap lyrics without sounding trite is a major achievement when you consider how few other artists managed to pull it off. And consider these lines, written nearly twenty years ago: “There’s war on the streets/And there’s war in the Middle East/Instead of wary on poverty/They got a War on Drugs so the police can bother me.” Plus ça change, plus c’est la même chose.

59. “It’s Funky Enough” – The D.O.C.

The fact that the samples all seem to be written in minor keys gives this song a sinister air that set it apart from most mainstream and alternative rap of the time. In the lyrics, the D.O.C. spends more time boasting about Dr. Dre’s prowess as producer than he does about his own rhyming skills.

58. “Keep It Underground” – Lords of the Underground

Not quite as campy as Onyx, but not quite as polished as Naughty by Nature, so they fell through the cracks as I mentioned above. But both of their songs on this list would have fit in well with the rap scene of the late 1980s before everything shifted with the rise of the west coast.

57. “Straight Outta Compton” – NWA

NWA’s press completely outstripped the quality of their output; they had two tremendous rappers in the fold, but their limited catalog was never as good as the hype or the controversy would indicate. They chose controversial subjects, which sold records and frankly was an important addition to a scene that had grown somewhat stale due to the lack of regional diversity. But that doesn’t make me more likely to reach for one of their records today.

56. “Same Song” – Digital Underground

The last gasp for these guys and the wax debut for 2Pac. I always loved that they named this EP release This is an EP Release.

55. “Lucas with the Lid Off” – Lucas

I believe I have two white rap artists on the list, and Lucas is one of them, although he used a sepia-toned video to obscure his race. The jazz-rap thing never really took off; there were scattered successes, a few of which are on this ranking, but as a movement it couldn’t sell enough records, instead producing more one-hit wonders like this one. Weird fact: Lucas’ father, Paul Secon, was a co-founder of Pottery Barn.

54. “I Got a Man” – Positive K

“Are you a chef? Cause you keep feeding me soup.” “I’m not waiting, because I’m no waiter/So when I blow up, don’t try to kick it to me later.” “All confusion, you know I solve ’em/You got a what? How long you had that problem.” So many great lines, and yet never forced.

53. “Wild Wild West” – Kool Moe Dee

One of the first rap songs to cross over in New York and get some time on MTV. It’s not Kool Moe Dee’s best rapping work, but the beat and (for the time) production values elevated it, and it inspired a remake and a film that we’d best pretend never happened.

52. “They Want Efx” – Das EFX

The list of allusions in this song would make the Beastie Boys proud, and of course their “iggedy” style of rapping spawned a brief craze that died quickly, probably because few rappers could actually pull it off.

51. “Bop Gun” – Ice Cube

The best of all of the George Clinton-inspired rap songs, in part because he appears on the track. Always liked Ice Cube holding up four fingers in the video when saying “Nineteen-ninety-THREE” (since the video came out in ’94). Cube’s a better technical rapper than he gets credit for, but he was best known at the time for violent, hate-filled lyrics that once caused Billboard to question whether one of his albums went beyond the boundaries of free speech.

50. “The Mighty Hard Rocker” – Cash Money & Marvelous

Just a vintage mid/late-80s east coast hip hop track, overlooked perhaps because they were only the second most-popular MC/DJ combo in Philly (and unlike the other pair, in this case the DJ was the central figure rather than the MC). It also didn’t help that the record label decided to market the Fresh Prince-like “Find An Ugly Woman,” which didn’t showcase the skills of either member – and, worse, wasn’t funny, either.

49. “It Takes Two” – Rob Base & DJ EZ-Rock

Hearing this song triggers a Pavlovian response in me where everything smells like Drakkar Noir.

48. “I Left My Wallet in El Segundo” – ATCQ

The best example I know of a rap song that tells a single story from start to finish, with Tribe’s trademark humor and weirdness. I actually own a limited edition 12-inch of this track on clear green vinyl.

47. “I Get Around” – 2Pac

“And I don’t know why/Your girl keeps pagin’ me.” Shock G and Money B of Digital Underground appear, but 2Pac makes it clear he was the best MC in the DU posse. The way his death was paired with Notorious B.I.G.’s as equivalent musical losses always bothered me – there’s no comparison, with 2Pac a top-5 all-time MC … when he wanted to be. Maybe in another universe he lived to see his mid-30s, stopped the “Thug Life” front, and became hip-hop’s most literate MC. Or maybe not.

46. “Steppin’ to the A.M.” – 3rd Bass

These guys always felt like they were trying too hard to establish their street credibility, as if they couldn’t wreck a mic without thinking, “We’re white.” I mean, I heard P.W. Botha never recovered from getting the gas face from MC Serch.

45. “Let Me Ride” – Dr. Dre

“Bodies being found on Greenleaf/With their fuckin’ heads cut off/Motherfucker, I’m Dre.” Talk about making your impression felt. Love the Ice Cube cameo in the video.

44. “Can I Kick It?” – ATCQ

Answer: Yes, you can.

43. “I Got It Made” – Special Ed

A lot of early hip-hop tunes came in for criticism because most of their songs were about nothing more than how talented the MCs in question were, but that doesn’t mean there weren’t better boasts and worse ones. The best rappers could drop clever rhymes to make the point for them, even if the music and production weren’t anything special. The sequence of lines in “I Got It Made” that includes “When I got too hot, I found a spot in the shade/And when my dishes were dirty, I got Cascade” seemed like a challenge of how far Special Ed could take the same basic rhyme and structure before he ran out of things to rhyme about.

42. “Protect Ya Neck” – Wu-Tang Clan

Wu-Tang are one of a handful of acts that ushered me out of hip-hop fandom; their style is very loose and unmetered, unlike the tighter rap style of 1980s east coast rap. You could argue that it’s almost improvisational, like a lot of jazz, but I never got into jazz either. This one track from their debut album is transitional, resembling the more structured rap hits that probably influenced these guys but with hints at the explosion that their next album would cause in the genre. My favorite Wu-Tang solo track came from my favorite Wu-Tang member on Twitter – Ghostface Killah’s “Daytona 500.”

41. “Potholes in My Lawn” – De La Soul

Absolutely hated this song when it first came out because it was so different from what I knew and liked of hip-hop up to that point. The problem wasn’t with the song, which boasted bluesy music and the great imagery that showed up all over 3 Feet High and Rising, but with the closed mind of a 15-year-old.

40. “I Go to Work” – Kool Moe Dee

If I worked in an MLB marketing department and wanted to put together a four-and-a-half minute highlight clip for a star player, this would be the backing track. The music is very James Bond, and Kool Moe Dee’s rhymes are faster and better than on his better-known “Wild Wild West.”

39. “Dre Day” – Dr. Dre featuring Snoop Doggy Dogg

The consummate diss track, with a lowbrow comic video to match. But even better now is the shot at around the 3:52 mark of the video of the guy on his cell phone the size of a brick and the shape of a satellite phone. I guess that was cutting edge in 1993.

38. “I Ain’t No Joke” – Eric B. & Rakim

Pretty sure this is the origin of the phrase “as serious as cancer,” as well as the song to which Shaq was referring with his “slam it … and make sure it’s broke” line at the end of the regrettable “What’s Up Doc (Can We Rock?).” Vintage Rakim across the board.

37. “The World is Yours” – Nas

Recently tweeted “Whose world is this?” and got a slew of responses involving lines from this song, more reasons why I love my readers. Illmatic was another rulebreaking record that didn’t do it for me when it first came out, and even now I don’t reach for any Nas tracks when I’m in the mood for hip hop – I have to be in the mood for Nas.

36. “Strictly Business” – EPMD

A solid track in its own right, elevated for me by the twin samples (“Let a sucker slide once, then I break his neck” and “I control your body”) used in Styles of Beyond’s 1999 track “Killer Instinct.” And Ryu of Styles of Beyond is the rapper on Crystal Method’s “Name of the Game,” which has nothing to do with EPMD but doesn’t fit in any other comment here.

35. “Mama Said Knock You Out” – LL Cool J

I feel like LL’s stature as a rap icon has dimmed as he’s become a mainstream Hollywood star, but he was relevant for almost a solid decade in the rap scene. Not only was this a tremendous track in its own right (although it’s ironic that the guy who said “I think I’m gonna bomb a town!” is now part of a secret spy team in LA fighting bad guys … trying to bomb that town), but with this song he was the biggest rap artist to perform his tracks live, including on live TV, with a backing band rather than just a DJ.

34. “Strobelite Honey” – Black Sheep

“Thank you for your time honey but ho I gotta go.” These guys were considered part of the Native Tongues group, but didn’t have the alternative vibe of De La Soul or the Tribe. They were, however, two-hit wonders, with this the funnier but less enduring of the two.

33. “I Get the Job Done” – Big Daddy Kane

That whole New Jack Swing movement didn’t last long and barely made a dent in the hip-hop scene, but this one collaboration between Kane and producer Teddy Riley, the top dog in the New Jack Swing arena (and the brains behind Wreckx-n-Effect and Blackstreet), was its finest moment. And Kane gave us lines like “So when your main course ain’t doing nothin’ for ya/Just think of me as a tasty side order.”

32. “Runnin’” – The Pharcyde

I’ve wondered if there’s a timing effect in our favorite songs by certain artists – the track you hear first becomes a standard against which you compare all future tracks from that artist, so it becomes your favorite or among your favorites by default. Or is it that you’re more likely to hear a top track first, because that’s how our music industry is (or, at least, has been) structured? Anyway, this was the first Pharcyde track I heard, and I’m pretty sure it’s their best. I think.

31. “Fight the Power” – Public Enemy

Although this appeared on Fear of a Black Planet, it was much more along the lines of the best tracks on It Takes a Nation of Millions to Hold Us Back, angry, loaded with powerful allusions and strong rhetoric, backed by a funky sample-filled music track that was among their best. I wonder if Chuck D still supports Tawana Brawley, whose claims of a violent assault by white public officials and police officers were discredited before the grand jury, and who appeared in the “Fight the Power” video.

30. “Paid in Full” – Eric B. & Rakim

I use the opening drum loop as the alarm tone on my cell phone. Stick with the original rather than the Coldcut remix.

29. “Mind Playin’ Tricks On Me” – Geto Boys

Aside from some confusion over the meaning of “bastard,” it’s a surprisingly thoughtful effort from a group better known for rapping about violence against women.

28. “Dirty South” – Goodie Mob
Before Cee-Lo was dressing up as Big Bird and performing with Muppets, he was part of a pioneering Atlanta hip-hop act that gave the Dirty South subgenre its name. (And his departure spurred the greatest diss album title ever: One Monkey Don’t Stop No Show.) This song and album just sneaked in under the wire, coming out in November of 1995, but the extent of social commentary and criticism under all the drug references harkened back to PE’s or Native Tongues’ best work from the late ’80s.

27. “93 ‘Til Infinity” – Souls of Mischief

The failure of the Hieroglyphics collective, which included Souls of Mischief and the next artist on this list, to find a mainstream audiences is one of the great commercial tragedies of hip-hop. Souls’ MCs, who were barely out of their teens when the album came out, had an easy, natural flow, and the production by Main Source and Gang Starr gave the album a jazzy feel without making it as inaccessible or distinctly noncommercial as a lot of jazz-rap tracks. Allmusic.com compared the album favorably to A Tribe Called Quest, but I think it’s more like a West Coast version of Tribe, harder lyrically and musically but with the same laid-back vibe.

26. “Mistadobalina” – Del the Funkee Homosapien

Ice Cube’s cousin. And the rapper on Gorillaz’ “Clint Eastwood.” I’m still not entirely sure what “Mistadobalina” is about but it’s been stuck in my head on and off for about twenty years.

25. “Doowutchyalike” – Digital Underground

The album version, which runs about seven minutes, is like a playground for Shock G and his Humpty Hump alter ego, way too long for mainstream radio, but unlike most songs of that length, it varies enough to hold your interest right up to the end. This is the track for which they should be remembered, not “The Humpty Dance,” although it hasn’t worked out that way.

24. “Jump Around” – House of Pain

“I got more rhymes than the Bible’s got Psalms/And just like the Prodigal Son, I’ve returned.” Best use of a Biblical reference to boast about one’s rhyming prowess, bar none. Their follow-up single, “On Point,” couldn’t match this song’s pop appeal, but did have a great line from Danny Boy: “Well, it’s the D to the A, double-N Y B-O/Why? Cause I rock shit like Ronnie Dio.”

23. “Microphone Fiend” – Eric B. & Rakim

“I was a fiend/Before I became a teen/I melted microphones instead of cones or ice cream.” “E-f-f-e-c-t/A smooth operator, operatin’ correctly.” “Cool, cause I don’t get upset/I kick a hole in the speaker, pull the plug, then I eject.” And that’s all from the first verse. There was no one like Rakim before he came along, and there has been no one like him since.

22. “Night of the Living Baseheads” – Public Enemy

Chuck D knew how to grab the listener’s attention with his first line, didn’t he? “Here is/Bam/And you say God damn/This is a dope jam.” I had always thought the sample played during the chorus breaks was something about a knife, but courtesy of Wikipedia and The-Breaks.com finally figured out last year that it’s “Twas the Night” from Curtis Blow’s “Christmas Rappin’.”

21. “California Love” – Dr. Dre and 2Pac

The best combo – can’t really call it a “duet” – of otherwise unconnected two rap artists in history, released on December 28th, 1995, just days before the cutoff for this list. The song’s chorus was sung by Roger Troutman of the group Zapp (“More Bounce to the Ounce”) in his last major appearance before he was killed by his brother in a murder-suicide.

20. “Gin and Juice” – Snoop Doggy Dogg

We know what #whitewhines are, so what do we call “With so much drama in the LBC/It’s kinda hard being Snoop D-O double-G?”

19. “So Wat Cha Sayin’” – EPMD

These guys boasted about their rhyming skills well above their actual abilities, but this was both their best-performed track and their strongest musically, in part because the samples didn’t overwhelm the rhymes like they did on “You Gots to Chill.” I’d prefer not to hear Erick Sermon try to sing Luther Vandross again.

18. “The Choice is Yours” – Black Sheep

“Engine, engine, number 9/On the New York Transit Line/If my train goes off the track/Pick it up, pick it up, pick it up!” It’s amazing that Black Sheep could put out two unbelievable tracks, and then never put out another song of value after that debut album.

17. “Ghetto Bastard” – Naughty by Nature

Of course, the one time NBN puts out a song of social commentary it doesn’t sell as well as the party tracks, so they went back to rapping about drinking and sleeping around. I can’t blame them, but there’s this barely contained rage in this song and a pretty strong argument in favor of nurture over nature.

16. “Going Back to Cali” – LL Cool J

The first alternative rap song to break through as a mainstream hit at a time when LL was veering dangerously into rap-balladeer territory. The structure is so unconventional at a time when nearly every hip-hop single followed the same pattern and subject matter that it probably only found airplay because of LL’s existing fan base, but that same break from the norm is what made it an instant classic.

15. “Streets of New York” – Kool G Rap & DJ Polo

One of two of my favorite tracks built off a sample of the Fatback Band’s “Gotta Learn How to Dance” along with Groove Armada’s “My Friend.” Kool G Rap’s mouthful-of-gold-teeth style can be a little offputting, like talking to someone with a giant plug of tobacco in his cheek, but like “Ghetto Bastard” this song has a serious point, and there’s a certain raw simplicity to it – he’s setting the scene, but offering no prescriptions – that gives it power even when the New York he’s describing has changed for the better.

14. “Award Tour “ – A Tribe Called Quest

Do dat, do dat, do do dat dat dat.

13. “Me, Myself And I” – De La Soul

So was the success of this song the worst thing to happen to De La Soul? They shied away from anything commercial on future albums, and what looked like a potential Hall of Fame career (because of their willingness to ignore the norms of hip-hop lyrics) ran off the rails after one album. Why didn’t they embrace their alternative-rap status and use it to move the genre forward? Or to at least just make themselves more money? Maybe they didn’t want to recreate 3 Feet High again, but they made it clear they wanted no part of mainstream success, and twenty years on I still don’t understand it.

12. “Player’s Ball” – Outkast

Apparently the Player’s Ball is a real thing, at least according to Wikipedia, which we know is never wrong. Fortunately, the song isn’t about that but about growing up in what was about to be called the Dirty South, with this staccato, off-beat delivery that sounds like you’re about to tumble down a flight of stairs.

11. “Rebirth of Slick (Cool Like Dat)” – Digable Planets

The best song to come out of the jazz-rap movement – not that that’s a high standard – built on a slowed-down riff from jazz pianist James Williams’ 1977 track “Stretchin’” and a drum loop from the Honeydrippers’ “Impeach the President.” The rhymes are surprisingly mundane, focusing again on the rappers’ skills, but the dark, descending bass line is the star of the show here.

10. “Raw” – Big Daddy Kane

See, if you’re going to dedicate the entire track to telling me about what a great MC you are, you need to back it up like this. Kane found commercial success with the Smooth Operator persona, but his legacy should start with this track, one of the best straight-up bragging songs in hip-hop history. “Cause I’m at my apex and others are below. Nothing but a milliliter, I’m a kilo.”

9. “T.R.O.Y.” – Pete Rock & C.L. Smooth

Dedicated to Trouble T-Roy, a member of Heavy D and the Boyz who died after falling from a balcony, the song is MC C.L. Smooth’s tribute to people who mattered in his life, including his single mother, an uncle who filled the role of father figure, and T-Roy. It’s smooth (he at least lives up to that part of his name) and soulful but never maudlin, and the sax sample from Tom Scott will be stuck in your head for weeks.

8. “No One Can Do It Better” – The D.O.C.

G-Funk before the term existed, and early evidence that Dr. Dre (who produced the album) was a force to be reckoned with beyond N.W.A. Twelve years after the accident that turned his powerful voice into a hoarse whisper, the D.O.C. is apparently headed for an experimental operation to restore much of what he lost, and in between his replies to friends you can see updates from him on his Twitter feed.

7. “Follow the Leader” – Eric B. & Rakim

I don’t think any single song got me into hip-hop more than this one; it is certainly the reason I’m a huge Rakim fan, and while it doesn’t have the same funky vibe as most of their other standout tracks, it has some absolutely vintage Rakim lines, including my favorite from him: “In this journey, you’re the journal, I’m the journalist/Am I eternal? Or an eternalist?” It ain’t braggin’ if you can do it.

6. “Talkin All That Jazz” – Stetsasonic

A strong defense of rap from early criticism by (white) media members, most of whom probably didn’t realize their kids were listening to the same music they were attacking. Hip-hop has done more to elevate the status o the bass line than any other movement in music history, and this one, borrowed from Lonnie Smith’s “Expansions” (and slowed down), might be the best.

5. “Bring the Noise” – Public Enemy

Gil-Scott Heron’s influence on Chuck D was all over their early work but never more apparent than on this track, a not-that-subtle call to black power where D was at his height in both lyrical content and the quality of the rhymes themselves, putting him with Rakim in his ability to craft the inside rhyme. But we’re just going to pretend that Anthrax cover never happened, OK?

4. “Hey Ladies” – Beastie Boys

The best track off the sample-laden album Paul’s Boutique, which itself was a major landmark in hip-hop that will likely never be repeated because of restrictive laws on sampling passed in its wake. (Of course, with the rise of downloadable music, the law seems strangely out of date now, as sampling could bring more attention to older tracks and spur sales that weren’t possible when those old records were out of print.) This album, and this track in particular, didn’t meet commercial expectations but established the Beastie Boys’ critical bona fides, particularly for their ability to craft clever lyrical allusions, setting them up for their second career as alternative artists that used hip-hop as opposed to garden-variety rappers. (Corrected on 7/7. The album wasn’t produced by Prince Paul, but the title pays homage to him.)

3. “Nuthin’ But A ‘G’ Thang” – Dr. Dre feat. Snoop Doggy Dogg

It’s funny that Snoop Dogg managed to upstage Dr. Dre, a strong MC in his own right, but that’s exactly what happened, with Dre shining more as a producer than a rapper. This song single-handedly elevated west coast rap over east coast and ushered in the G-Funk era, which was later hoisted on its own petard by Warren G’s regrettable “Regulate,” for better (stronger production values and a heavier emphasis on 1970s funk) and worse (a subsequent drop in lyrical quality from those who imitated the subject matter but couldn’t rhyme like Dre or Snoop).

2. “Scenario” – A Tribe Called Quest featuring Leaders of the New School

Busta Rhymes’ breakout track – unless you count “Case of the PTA,” which I don’t – was also Phife Dawg’s best work, with some of the best call-and-response lines (“Who’s that?” “Brown!”) in rap history. If there’s a flaw here, it’s that there’s not enough Q-Tip, but every other MC stepped up his game to fill the gap in a signature moment for east coast rap.

1. “I Know You Got Soul” – Eric B. & Rakim

The best MC in history has to be at the top of the list, right? Especially when his DJ paired him with one of its most memorable beats (based on Bobby Byrd’s song of the same name), and the MC in question brought his A-game in a track that has been referenced regularly for 20 years, including its opening lines: “It’s been a long time/I shouldn’t’ve left you/Without a strong rhyme to step to/Think of how many weak shows you slept through/Time’s up, I’m sorry I kept you.” Rakim’s line “pump up the volume” spawned a M/A/R/R/S song and a teen-angst movie (that I admit, I loved, and have seen at least three times), and Eric B.’s heavy use of James Brown is credited with spurring a revival of interest in Brown’s music through increased sampling in hip-hop tracks. Both guys were at the tops of their games – I like to think that the music pushed Rakim to deliver one of his two best performances – and it has proven both enduring and influential even as the artists themselves have faded from the scene. There’s no better track in old-school hip-hop than this one.

So what songs did I miss? What artists? I’ll admit up front I’m not a big B.I.G. fan, and many of the poppier acts of the 1980s (Kid ‘n Play, DJ Jazzy Jeff & the Fresh Prince) never did much for me when they were current. But I look forward to your suggestions and comments.