My Top 100 Rap Singles of the 1990s
Over the past year I've posted lists of my favorite R&B, pop, and rock singles of the 1990s. But I found this one particularly exciting and a little daunting to work on, because there may be no genre that exploded more creatively and commercially in a 10-year period as much as hip-hop in the '90s. Even in these 100 songs I think I'm only scratching the surface, but I tried to at least suggest the incredible range that rap had even at the mainstream level in the '90s. Here's the Spotify playlist, which has everything except one of the versions of "Deep Cover," and has unfortunate clean edits of a couple songs:
1. Notorious B.I.G. - "Juicy" (1994)
Now and again, I hear some rising rap star for the first time, and their breakthrough single sounds like a self-congratulatory look back at their long 16 or 22 years of life before they made in the music industry, and here they are, a star. And I shouldn't be annoyed, because these kinds of songs are direct descendants of the first single from the first Biggie Smalls album. But then, nobody ever did it better than Biggie. I've never been big on singing or rapping along with music while I listen to it, and I rarely memorize a verse well enough to rap along with it anyway, but this is definitely one of those few songs I know word for word.
2. Geto Boys - "Mind Playing Tricks On Me" (1991)
So much of the Geto Boys' music was shock rap that works as pure provocation. "Mind Playing Tricks On Me" still has a horror movie atmosphere to it (including a dream sequence that takes place on Halloween), but it's much more psychological and ruminative. Scarface has an incredible catalog, but producing "Mind Playing Tricks" and writing 3 of its 4 verses is easily his crowning achievement.
3. A Tribe Called Quest f/ Leaders Of The New School - "Scenario" (1992)
The Low End Theory is my #1 rap album of all time, so I knew this had to be pretty high up on the list. The posse cut has become kind of a leaden ritual of mainstream hip hop, DJ Khaled packing MCs on songs to show off his clout or all-star remixes trying to push a hit single further of a charts. But the oneupsmanship that a good posse cut can bring out of MCs is a powerful force, and nobody's exploited it better than Busta Rhymes, who shined so bright on "Scenario," where every verse is great, that he all but ensured that Leaders Of The New School would break up and that his solo career would far surpass the group's success.
4. Snoop Doggy Dogg - "Gin And Juice" (1994)
Although I love the rawer sound of '80s hip hop, it's really remarkable how much a handful of great artists spurred each other to refine and heighten rap production in the early '90s. What Ali Shaheed Muhammed and Q-Tip did on The Low End Theory inspired what Dr. Dre did on The Chronic, which in turn inspired Tribe's Midnight Marauders. Snoop's charisma on those Chronic and Doggystyle hits is overwhelming that you almost forget how beautifully constructed those beats are, but for me Snoop and Dre's tag team peaked with "Gin And Juice." I love how those 4 bass notes kick off the track. By the way, people always quote "with my mind on my money and my money on my mind" as a Snoop line, but it's definitely someone else's voice on that part. But who? Sounds like it could be Dre or Daz but I'm not sure.
5. Warren G and Nate Dogg - "Regulate" (1994)
Death Row's roster of talent was so deep that they didn't even bother to sign Snoop's old Long Beach friends or their group 213, even after Nate Dogg and Warren G made essential contributions to most of the label's classic albums (although the pair of Death Row guys that got branded by the label as Snoop proteges, Daz and Kurupt of the Dogg Pound, became West coast legends too). But Warren and Nate still made themselves into stars off the strength of gangsta rap's smoothest smash, sampling Michael McDonald for a hit off Death Row's soundtrack for Above The Rim. "Regulate" blew up the same summer as "Thuggishh Ruggish Bone," and Nate Dogg and Bone Thugs-n-Harmony are probably equally pivotal figures in turning rap singing or melodic rapping into an artform in its own right.
6. Wu-Tang Clan - "C.R.E.A.M." (1994)
Before I even heard Wu-Tang's breakthrough single, I heard kids quoting the hook, and in my mind "cash rules everything around me, cream, get the money, dolla dolla bill y'all" sounded like one of those choruses where a DJ scratched together phrases from 3 or 4 different records. It was only later in listened to the song that I realized Method Man was just casually spitting the whole thing. It's crazy to think this was most people's introduction to Wu-Tang, and a great one, but it was still only the tip of the iceberg, a song that only involved 4 of the 9 members of the group.
7. Pete Rock & C.L. Smooth - "They Reminisce Over You (T.R.O.Y.)" (1992)
Although many of the rap legends who died young have been memorialized in song (most famously, for better or worse, "I'll Be Missing You"), the most profound expression of grief in hip hop might be Pete Rock's dedication to a relatively minor figure, Heavy D & The Boyz dancer Trouble T Roy. Pete Rock says he cried while making the song, and the emotion just pours out of the track, but even on a technical level the drum programming is incredible, the snare hitting all these little unpredictable accents more like a jazz drummer than a drum machine.
8. Queen Latifah - "U.N.I.T.Y." (1994)
As you can see from the last 3 songs, acronyms were very big in '90s hip hop, although "U.N.I.T.Y." didn't really stand for anything in the song, Latifah was just spelling out the word. There was nearly decade where Salt-N-Pepa reigned as the biggest female rap act, but a lot of great solo MCs thrived in that era too, and "U.N.I.T.Y." and MC Lyte's "Ruffneck" were such badass, tough-sounding songs that really changed my perception of women in hip hop.
9. 2Pac - "Keep Ya Head Up" (1993)
It's funny that even as the criteria for good rapping continues to expand as hip-hop evolves, people still seem to bend over backwards to insist that Tupac Shakur wasn't a good rapper. But he was one of rap's greatest songwriters, with a great ear for flows, phrasing and rhetoric that more that made up for his shortcomings in rhymes, and "Keep Ya Head Up" is one of the songs I come back to the most
10. DMX - "Ruff Ryders Anthem" (1998)
The Swizz Beatz sound inelegantly stuck out like a sore thumb amidst all the sleeker, more artful rap production of the second half of the '90s. But I think one of the reasons DMX was the guy who stamped Swizz at a hitmaker is he was such a seasoned MC, honing his craft for a decade before he exploded in '98, who could dart around those simple beats with all these jazzy little accents that made a song like "Ruff Ryders Anthem" sound like more than the sum of its harts.
11. LL Cool J - "Mama Said Knock You Out" (1991)
The scene in Chris Rock's 2014 movie Top Five where Rock's character names his top five rappers culminates in him sheepishly adding "my 6th man's LL Cool J," and then, shouting over his friends' derision, defensively adding "BEFORE THE SHOW!" (the show being LL's 1995-1999 sitcom "In The House"). But LL Cool J coined the term GOAT and he's still one of rap's GOATs, and "Mama Said Knock You Out" sits nicely as the pinnacle at almost the exact halfway point of his historic run as one of the greats, the top of the pyramid of his career.
12. Outkast - "ATLiens" (1996)
I can remember reading reviews of ATLiens in a couple magazines before I'd ever heard Outkast and being really intrigued (I also hadn't heard Atlanta referred to as the A-T-L so I had the completely wrong idea of how ATLiens was pronounced). Nowadays I like their early stuff best, and kind of gravitated to this as my dark horse favorite of their '90s singles, I feel like it's onne of their best-sounding beats, notably self-produced by Andrew and Big Boi rather than by Organized Noize.
13. Juvenile - "Ha" (1998)
Even though No Limit had brought the national spotlight to New Orleans and no doubt motivated Universal's $30 million investment in Cash Money Records in 1998, "Ha" sounded like it had been beamed in from another planet when it showed up on MTV. And even after "Back That Azz Up" made good on Universal's bet and 400 Degreez went quadruple platinum and we got a lot more used to Mannie Fresh's beats and Juvenile's voice, "Ha" still sounds bold and bizarre as the launching pad for southern rap's most profitable empire.
14. Puff Daddy f/ The LOX, Lil Kim and the Notorious B.I.G. - "It's All About The Benjamins (Remix)" (1997)
"Benjamins" would've been the hardest song Bad Boy ever put out even if it remained the original mixtape version with just Puff, Jada and Sheek (which, fascinatingly, was put together by an uncredited Missy Elliott). But the addition of the iconic Lil Kim verse and the incredible beat switch for the Biggie verse really put it into another stratosphere. It's weird to think that I didn't really like this song when it first came out.
15. Craig Mack - "Flava In Ya Ear" (1994)
It's tempting to opt for the remix of "Flava In ya Ear," which is the gold standard everyone aims for when making an all-star remix to a hit song. But I think the late Craig Mack deserves some credit for how killer this song is in its original incarnation. In college I had a roommate who loved this song so much that he memorized all the lyrics, and honestly all three of Craig's verses are as great as the verses on the remix.
16. Mobb Deep - "Shook Ones Part II" (1995)
Now I'm sad noticing that I just put three songs in a row with rappers that have passed away. I'm glad I got to interview both members of Mobb Deep while the group was still together, though, and their music has aged incredibly well, especially The Infamous. As someone who's tried recording a lot of household objects and knows that turning them into music very rarely actually works and sounds good, I'm in awe of how Havoc made one of the hardest beats of all time by turning the sound of a stove igniting into a hi-hat.
17. Souls Of Mischief - "'93 Til Infinity" (1993)
There are a few songs on here that I don't think I actually heard until the '90s were over, and this is definitely one of the highest. Just an incredible beat with so much energy and personality in the verses, makes me feel like the Hieroglyphics crew could've made a lot more mainstream hits beyond this song (although one of the guys shouted out at the end of "'93 Til Infinity," Del The Funky Homosapien, was later on a pretty big Gorillaz song).
18. Method Man f/ Mary J. Blige - "I'll Be There for You/You're All I Need to Get By" (1995)
Hip hop was a close neighbor to R&B from the beginning, and somewhere between Jody Watley and Rakim's 1989 hit "Friend" and Ja Rule's string of hit duets in the early 2000s, a durable formula of guys rapping verses and girls singing hooks emerged as a perennial chart staple. And perhaps the greatest example of the form is, fittingly, the Queen of Hip Hop Soul and one of rap's most enduring heartthrobs putting a twist on a classic Marvin Gaye/Tammi Terrell duet. The "All I Need" without Mary J. Blige on Tical has little to do with the the 2 hit versions -- I hear the Puff Daddy mix on the radio more, but I always preferred the RZA-produced Razor Sharp Mix that appears in the video, so that's what I put on the playlist.
19. Busta Rhymes - "Put Your Hands Where My Eyes Could See" (1997)
Busta Rhymes appeared on and made hits throughout nearly the entire decade, but it feels right that he really hit his peak of ubiquity in 1997, when he became the ideal muse for Hype Williams and served as an animated counterpoint to the more laconic figures like Puffy and Ma$e. "Put Your Hands Where My Eyes Could See" probably had some minor imitators but it always feels like it sits apart from the other hits of '97, that Seals and Croft sample sounds so ominous and almost menacing in this context.
20. Jay-Z f/ Jaz-O and Amil - "Jigga What, Jigga Who (Originator '99)" (1999)
Jay-Z made four of his best albums in the '90s, including his biggest seller, but it feels like his 20th century fame only hinted at the kind of dominant GOAT figure he'd become in the new millennium. Similarly, Timbaland's biggest chart success came in the 2000s, but he really broke the mold and revolutionized R&B and then hip-hop production in the '90s. And when Jay and Timbo started working together, some serious magic started happening.
21. N.O.R.E. - "Superthug" (1998)
Much like their hometown Virginia Beach pal Timbaland, Pharrell Williams and Chad Hugo of The Neptunes got their foot in the door apprenticing with R&B hitmakers, but their inventive signature sound really blossomed once they started getting in the studio with rappers. It's funny, I experienced a lot of the music on this list primarily when the videos came on MTV or BET or The Box, and sometimes TV speakers really didn't do the music justice. So I liked 'Superthug" at the time, but mainly as this silly song where the whole hook was "what what what what what," and it took me a few years to realize how crazy the beat was.
22. Luniz - "I Got 5 On It" (1995)
About a decade ago, Spin asked me to put together a list of the biggest Hot 100 hits about or mentioning weed, and "I Got 5 On It" ranked at #9. If Id ordered the list by quality, though, this song would #2 behind "Gin & Juice."
23. EPMD - "Crossover" (1992)
I think more than most rappers of the late '80s and early '90s, EPMD provided a template for the sound and attitude of popular hip-hop in the decades to come. But in their moment, EPMD were kind of underdogs, scoring a string of gold albums while the few multiplatinum rap albums were by guys more like MC Hammer. So it's a little ironic that EPMD's biggest hit is the one decrying crossover appeal.
24. Gang Starr - "Mass Appeal" (1994)
Another brilliant song decrying catering to the masses that happened to be catchy enough to become the group's biggest Hot 100 hit. DJ Premier is still probably my top hip hop producer of all time, and one of my favorite moments as an interviewer was talking him on the phone a few years ago and hearing him explain different kinds of DJ scratches and imitate them with his voice.
25. 3rd Bass - "Pop Goes The Weasel" (1991)
And now 3rd Bass is our third group in a row who scored their biggest hit (in their case their only Hot 100 hit) by denouncing other rappers who went pop. Of course, 3rd Bass had the additional anxiety of being one of the most prominent white groups in the aftermath of the enormous success of the Beastie Boys and Vanilla Ice. Hilariously, 3rd Bass had Henry Rollins play Vanilla Ice in the "Pop Goes The Weasel" video, but even as satire it's a good pop rap song, trading in the Queen and David Bowie sample for an inspired combination of Peter Gabriel and The Who samples.
26. Naughty By Nature - "O.P.P." (1991)
As much as the early '90s were the disheartening MC Hammer era of pop rap, there were some genuinely great crossover hits in those years. As a prepubescent kid I barely understood "O.P.P." and that made the song seem even dirtier to me than it really was, but man, what an insanely catchy song, Treach had such a star quality that it always surprised me he never had a big solo career. Hilariously, practically the only line in the song that isn't sexual innuendo is the part where Treach tells the guy who programmed the bassline, "Dave, drop a load on 'em."
27. Digital Underground - "The Humpty Dance" (1990)
As with "O.P.P." I think a lot of the innuendo of "The Humpty Dance" went over my head at the time. It's such a deliriously entertaining song, though, Digital Underground deserved to be known for more than this song, but it seemed like Shock G was cool with Humpty Hump being a big part of his legacy. I kind of associate "The Humpty Dance" with things like "Love Shack" and "Groove Is In The Heart," songs that made popular music seem absurdly campy but irresistibly fun when I first started to really pay attention to what was going on.
28. Biz Markie - "Just A Friend" (1990)
Biz Markie died last year just a couple months after Shock G, and it felt like a very sad period that also underlined that both of these guys demonstrated how it was possible to be a total fun-loving goofball but also embody hip-hop to the core.
29. DJ Jazzy Jeff & The Fresh Prince - "Summertime" (1991)
He's The DJ, I'm The Rapper was the first rap album I ever heard when hanging out with one of my older cousins, and it's a pretty perfect kid-friendly record to seduce suburban kids to the charms of hip hop. But by the time Will Smith made his best and most enduring song, he had already made the jump to acting with the first season of "The Fresh Prince of Bel-Air," paving the way to make a bigger impact on the box office than he'd ever made on music.
30. Positive K - "I Got A Man" (1993)
I thought "I Got A Man" was one of the funniest songs I'd ever heard for about a decade before I even realized that the 'girl' on the song was actually also Positive K with his voice pitch-shifted up. But it still feels like a classic of the 'battle of the sexes' rap subgenre, alongside "Bitties In The BK Lounge," "Nann," and "Chickenhead."
31. Sir Mix-A-Lot - "Baby Got Back" (1992)
Another cartoonishly silly crossover hit that I still think took a ton of talent to rap and produce. In another world, Sir Mix-A-Lot probably could've continued on the path of "Posse On Broadway" and become a respected trailblazer for northwest rap who's not associate with a novelty song, but I'm glad we live in a world where I can listen to "Baby Got Back" ever now and again.
32. Lost Boyz - "Renee" (1996)
I remember when I met one of my favorite Baltimore rappers, Tate Kobang, and I thought it was cool as hell that this talented kid barely out of his teens namechecked Lost Boyz-era Mr. Cheeks as one of his biggest influences. "Lights, Camera, Action" was fun and all, but "Renee," man, that's an incredibly well written song.
33. Ice Cube - "It Was A Good Day" (1993)
"It Was A Good Day" is pretty atypical for one of the West Coast's greatest MCs. In fact, it kind of sounds like every other song Ice Cube made for the first decade or so of his career was recorded on a bad day. But it's still a great showcase for Cube's skill as a writer, and the way he took the kind of laid back new wave of gangsta rap that his former groupmate Dr. Dre had spearheaded, and turned it into this dryly funny satirical narrative about a day in the life of an L.A. badass.
34. Nas - "It Ain't Hard To Tell" (1994)
Being a kid who didn't really know much about hip-hop beyond what I saw on "Yo! MTV Raps," I never heard of Nas until "If I Ruled The World" and It Was Written. Even the one Hot 100 entry from Illmatic somehow missed me, and I didn't pick up Nas's debut or understand why he was so revered until, I dunno, 2002? But I'm kind of surprised "It Ain't Hard To Tell" wasn't bigger at the time, it's such a perfect closer for the album, I don't know if it helped or hurt Nas that SWV had just done their "Human Nature" sample 2 years earlier.
35. Jeru The Damaja - "Come Clean" (1994)
Wierdly, though I didn't hear a word about Illmatic in '94, I remember MTV showering more attention on Jeru The Damaja's album than Nas or Biggie's legendary debuts at the time. "Come Clean" was probably the first DJ Premier production I ever heard, and it really is a memorably weird track.
36. Missy Elliott - "The Rain (Supa Dupa Fly)" (1997)
As much as my memories here are invariably tied up in MTV, "The Rain" is probably one song that everybody thinks of as inextricably linked to its music video. Like Juvenile's "Ha," I think of "The Rain" as a gutsy, atypical song to use to introduce the artist to the national public, but it worked in a similarly enormous way.
37. LL Cool J f/ LeShaun - "Doin' It" (1995)
In addition to being arguably the #1 MC of hip hop's first two decades, LL Cool J often seems like one of the most dangerously horny men who ever lived, and in that sense "Doin' It" is the most LL song LL ever made. The female MC on the song, LeShaun, absolutely killed the track, which was apparently based on one of her solo songs. Unfortunately, LL and Hype Williams decided to cast other women to lip sync LeShaun's verses in the video because she was pregnant, and her career never really progressed beyond that one hit, and I have to wonder if she could've hung with Kim and Foxy if she got the chance.
38. Big Punisher f/ Joe - "Still Not a Player" (1998)
It always amuses me when two songs get smushed together into something that becomes far bigger than either of the originals (like "Teach Me How To Dougie," which totally eclipsed "Teach Me How To Jerk" and "My Dougie"). It was pretty clever for Big Pun to combine his single "I'm Not A Player" with Joe's single "Don't Wanna Be A Player" into a new song, but those of us who hadn't heard either needed no context to love it. I'm still irritated that "Still Not A Player" appears before "I'm Not A Player on Capital Punishment, though, that's just bad sequencing!
39. Salt-n-Pepa f/ En Vogue - "Whatta Man" (1993)
Salt, Pepa and Spinderella were the top-selling women in hip hop for almost a decade, and their collaboration with the top girl group of the early '90s was really just an inspired pairing, really a great example of how fun and full of personality a pop rap song can be.
40. Black Sheep - "The Choice Is Yours (Revisited)" (1992)
The aptly named Black Sheep never really built a legacy as significant as the other Native Tongues groups, but this is probably one of the top 3 best Native Tongues singles. I saw Black Sheep play the Ottobar in Baltimore around I think 2002 or 2003, and those guys really know how to put on a show. The place absolutely exploded when they broke out "The Choice Is Yours," might be a top 5 live hip hop moment for me.
41. UGK f/ Smoke D - "Front, Back & Side To Side" (1994)
UGK were one of the best southern rap groups of the '90s, but they didn't really start to get even half of the mainstream profile they deserved until "Big Pimpin'" and "Sippin' On Some Syrup" hit just after the decade ended. Those first four albums are full of classic songs, though, with "Front, Back & Side To Side" giving them an early taste of national radio airplay in '94, and again in 2006 when they remade the song with T.I.
42. Goodie Mob - "Cell Therapy" (1995)
Outkast's debut single "Player's Ball" hit #37 on the Hot 100, and from there the duo kept climbing until they started making #1s. Their Dungeon Family compatriots in Goodie Mob hit #39 with their debut single, but then they got any higher on the charts after that. And it's a shame that they don't really get their due as more than 'Cee-Lo's old group' for classics like Soul Food.
43. The Roots f/ Erykah Badu and Eve - "You Got Me" (1999)
Playing drums was a big part of my gateway to loving hip hop, just appreciating the way the mix is centered on the drums and there's such a wide variety of textures and rhythms in the percussion on rap records. But sure, at one point was also a little closed-minded as a white rock musician who lamented that loops and breaks were replacing human drummers. Once I came to respect the art of beatmaking, though, I also gained a richer appreciation for The Roots' singular achievements in the genre and the way Questlove mastered both the drum set and the drum machine. And "You Got Me," with its sneaky transition from a delicate live R&B groove to the skittering drum'n'bass outro, is one of his finest moments. "You Got Me" and Things Fall Apart blew me away when I was 17, and I remember learning about the launch of OkayPlayer.com via the album's liner notes, so writing my first piece for the site earlier this year was a big deal for me.
44. Black Star f/ Common - "Respiration" (1999)
The whole idea of "conscious" rap being this sort of adversarial corrective to mainstream hip-hop really peaked in the late '90s, and that era has aged in weird ways. But Mos Def, Talib Kweli, and Common all made some great music then, and even though it wasn't really much of a hit, "Respiration" really stands out as a masterpiece, Mos in particular really did something special on that record.
45. Cypress Hill - "Insane In The Brain" (1993)
"Insane In The Brain" was a hit on the rap charts and not the rock charts, but it feels like that song was the start of this weird drift were Cypress Hill kind of got adopted as an 'alternative' group that got played on MTV's "Alternative Nation" and some rock stations alongside white rap groups like Beastie Boys and House of Pain and co-headlined Lollapalooza. Was it because they were synonymous with smoking weed, or because they were Latino? I dunno. But still, a great song, and I was so disappointed just now to put on the album version of "Insane In The Brain" and not hear the Youngbloods "I think I'm goin' crazy" sample that's at the end of the video mix.
46. Sagat - "Why Is It? (Funk Dat)" (1994)
I've spent a lot of the last 2 decades writing about Baltimore hip hop and watchfully noting the rare occasions when a Baltimore rapper made it to the Billboard charts, from B. Rich to Shodie Shordie. But back in the '90s, the only guy from the city who had a moment like that was Sagat and his odd hip house track full of Seinfeld-like gripes about modern life. Who was this guy and what was his deal? To this day, I have yet to meet anybody in the city who knows him or anything about him.
47. Arrested Development - "Tennessee" (1992)
While I'm casually admitting corny things about my history as a white kid listening to hip hop, let me just admit that the first rap CD that I ever bought was Arrested Development, and not the big album everyone had, I got the Unplugged album. I mostly find Arrested Development embarrassing now, but "Tennessee" actually sounds better to me now than it did in the '90s, great record. It's funny to think that Baby Tate, a rising rapper in 2022, is the daughter of Dionne Farris, the singer at the end of "Tennessee"
48. The Fugees - "Fu-Gee-La" (1996)
The Fugees became bigger and more iconic than Arrested Development, especially once they launched solo careers, but I think of them in similar terms as respectable granola post-Native Tongues pop rap, and I have little desire to listen to much of their stuff these days. This song kicks ass, though.
49. Camp Lo - "Luchini (This Is It)" (1997)
Ski Beatz produced back-to-back classics in Jay-Z's Reasonable Doubt and Camp Lo's Uptown Saturday Night, and legend has it Jay wanted the "Luchini" beat. That's an exciting hypothetical to think about, but I wouldn't change how things went down, it was the perfect track for Sonny Cheeba and Geechi Suede to talk their inscrutable and deeply coded shit over.
50. Domino - "Getto Jam" (1994)
Domino is one of those fleeting '90s rap stars that I think has been lost to time, but if you were alive back then, you probably remember at least one of the two Top 40 hits from his gold-selling self-titled album. Domino lived in Long Beach and probably got his record deal because Def Jam was looking for the next Snoop Dogg. But Domino was born in St. Louis, which is kind of interesting considering that he was one of the first rappers with a really melodic flow to hit the top 10 over half a decade before Nelly took melodic rapping to new heights.
51. Public Enemy - "911 Is A Joke" (1990)
52. Chubb Rock - "Treat Em Right" (1992)
53. 2Pac f/ Digital Underground - "I Get Around" (1993)
54. DJ Kool - "Let Me Clear My Throat" (1997)
55. Bone Thugs-N-Harmony - "Thuggish Ruggish Bone" (1994)
56. Dr. Dre f/ Snoop Dogg - "Nothin' But A 'G' Thang" (1993)
57. Silkk The Shocker f/ Mystikal - "It Ain't My Fault" (1998)
58. Ol Dirty Bastard - "Brooklyn Zoo" (1995)
59. Juvenile f/ Mannie Fresh and Lil Wayne - "Back That Azz Up" (1999)
60. Akinyele f/ Kia Jeffries - "Put It In Your Mouth" (1996)
61. Xzibit - "What U See Is What U Get" (1998)
62. A Tribe Called Quest - "Award Tour" (1993)
63. DMX - "What's My Name?" (1999)
64. Lil Kim f/ Lil Cease and Notorious B.I.G. - "Crush On You" (1996)
65. Jermaine Dupri f/ Jay-Z - "Money Ain't A Thang" (1998)
66. Mobb Deep - "Quiet Storm" (1999)
67. Gang Starr f/ Nice & Smooth - "DWYCK" (1994)
68. Makaveli f/ Outlawz - "Hail Mary" (1997)
69. Busta Rhymes - "Gimme Some More" (1998)
70. MC Lyte - "Ruffneck" (1993)
71. Outkast - "Player's Ball" (1994)
72. Queen Latifah f/ Monie Love - "Ladies First" (1990)
73. Dr. Dre f/ Snoop Dogg - "Deep Cover" (1992)
74. Big Punisher f/ Fat Joe - "Twinz (Deep Cover '98)" (1998)
75. DMX - "Get At Me Dog" (1998)
76. Lord Tariq & Peter Gunz - "Deja Vu (Uptown Baby)" (1998)
77. Notorious B.I.G. f/ Mase and Puff Daddy - "Mo Money Mo Problems" (1997)
78. Trick Daddy f/ Trina - "Nann" (1998)
79. Naughty By Nature - "Hip Hop Hooray" (1993)
80. Wu-Tang Clan - "Triumph" (1997)
81. Jay-Z - "Hard Knock Life (Ghetto Anthem)" (1998)
82. Heavy D & The Boyz -"Black Coffee" (1994)
83. Tear Da Club Up Thugs f/ Project Pat - "Slob On My Knob" (1999)
84. Eric B. & Rakim - "Juice (Know The Ledge)" (1992)
85. Nonchalant - "5 O'Clock" (1996)
86. Lauryn Hill - "Doo Wop (That Thing)" (1998)
87. Scarface - "I Seen A Man Die" (1994)
88. A Tribe Called Quest - "Check The Rhime" (1991)
89. Notorious B.I.G. - "Big Poppa" (1995)
90. Da Brat - "Funkdafied" (1994)
91. Onyx - "Slam" (1993)
92. Lil Wayne f/ Juvenile & B.G. - "The Block is Hot" (1999)
93. Jay-Z f/ Foxy Brown - "Ain't No" (1996)
94. The Pharcyde - "Passin' Me By" (1993)
95. Do Or Die f/ Twista and Johnny P - "Po Pimp" (1996)
96. Busta Rhymes - "Woo Hah!! Got You All In Check" (1996)
97. Dr. Dre f/ Snoop Dogg - "Let Me Ride" (1993)
98. The Lost Boyz - "Jeeps, Lex Coups, Bimaz & Benz" (1995)
99. DMX - "How's It Goin' Down" (1998)
100. LL Cool J - "Jingling Baby" (1990)
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