Playlist: Best Hip-Hop Songs of the 90s

If you haven’t known me for a long time, it might surprise you to learn that I spent my youth listening to hip-hop. Exclusively. (I suppose the flip side of that is that if you only knew me then, you’d be shocked to learn that I no longer listen to hip-hop. The rest of you probably just clicked here due to some search, and are wishing I’d get on with it already). I don’t listen to it much anymore, other than the most popular, backpacker types (Common, Kanye, Lupe Fiasco, etc), nor do I listen to the music of my youth that often. I pared down my hip-hop CD collection from 400+ to somewhere around 30, and thrust myself into the world of indie rock as hard as I once followed urban American music.

My reasons for changing genres are varied. I’ll try to avoid sounding like a lot of douchebags who say that hip-hop was only good when I was young, but as it got more commercial, it did lose some appeal. But that’s not just it, because I could have simply turned away from the 50 Cents of the world to independent hip-hop artists like Jurassic 5. Nor am I going to suggest that I somehow came to my senses. Hip-hop is a valid art form, and the stuff I listened to in my youth was usually pretty good (well, more often than not). But, I do think growing up had a lot to do with it, not that the music is necessarily immature, but it is youth-orientated, more so than even rock-n-roll. At the time, while I couldn’t exactly relate to the plight of urban African-Americans, I could relate to the youthful energy and the frustration of being an outcast, as all teenagers feel like that. And hey, maybe it was simply because 90s rock music sucked (I don’t mean that. Well, not completely).

But just because I gave it up, doesn’t mean I don’t get nostalgic from time to time. And thus, I put together this playlist, audaciously titled “Best Hip-Hop Songs of the 90s”. I’ll cop to this right now: these are in no way THE 18 best hip-hop songs from the 90s. This is a playlist instead of a list-list, so the goal was to not just put the best songs that I could on it, but also to come up with a CD that flowed well and represented a good range of hip-hop throughout the decade. So when I was putting this playlist together, I did so with these guiding principles in mind:

1. No more than one song per artist- This one should be a given, and is a rule I’ve followed in mix-making most of my life. If you pack a mix with the same artist, it no longer feels like a mix, now does it? (The exception being, of course, single-artist career-spanning mixes). So for this playlist, I had to find the best songs from some my favourite artists, whereas if it were simply a listing of the 18 best songs, some artists double up. Note: the other exception to this rule is if an artist appears on another artist’s song, or in the case of group and solo work (e.g., Method Man appears both as a member of the Wu-Tang Clan and for his own song).

2. Songs must flow well into one another- Given that this is already a chronological mix subject, I decided to arrange the songs by year. That way I could follow the music from junior high through to high school and finish in college. This chronological order gave me less flexibility in ensuring good flow, so sometimes superior songs were cut from the playlist simply because they didn’t sound good with the other songs near it. This led to what might be my favourite hip-hop songs from the 90s, Public Enemy’s “Welcome to the Terrordome” being cut from the playlist. It sounded too different from everything else, and didn’t feel like a good way to start the playlist.

3. It had to fit on one CD- I’ll be enjoying this mix on my iPod, where length doesn’t matter. But I also wanted to record it as a mix for friends, so I had to make sure it fit on a CD. This is why it’s 18 tracks long, instead of a figure that makes more sense, like 20. Also, this resulted in longer songs getting cut in order to fit more songs in (so a five-minute plus song would get cut instead of two 3 minute tracks).

4. I had to still enjoy the song for more than nostalgic reasons- When compiling the playlist, I either ripped or downloaded plenty of albums from my youth, and enjoyed listening to many of them. But then I tried to separate my nostalgia from my genuine feelings, trying to decide whether or not I’d still listen to a song like it if I were to hear it for the first time now. The result was basically no gangsta rap, and very little misogyny, which is a positive. It also led to even more of a backpacker feel. So be forewarned.

5. Awkward intros and outros led to deletion- Even when I lived and breathed this stuff, I couldn’t stand how much space was wasted on hip-hop albums with annoying skits. Worse is when they bled into tracks, so songs that featured awkward intros or outros with the track were usually deleted. The big exception is with the first track, which has a brief intro, but that plays better given that it is the first track.

So keep these rules in mind as you go through the list, and feel free to listen to the tracks. In fact, I kinda hope you check at least some of them out, given that I just bought more memory for this blog so I could put them up in here. So follow me back to the days of Starter caps and Timberland boots…

1. Can I Kick It? – A Tribe Called Quest (1990)
This song has practically become a hip-hop standard, used in any film or commercial looking to evoke the early 90s, powered by the sample of Lou Reed’s “Walk on the Wild Side”. I didn’t actually get into the Tribe until 1991’s Low End Theory, with this song marking one of the rare instances of me seeking older albums of an artist. At the time, I was always focused on staying current with music (a problem a lot of young people have, and not just with music), ignoring things even if they were merely a year old. But I couldn’t ignore this track, forcing me to track People’s Instinctive Travels and the Paths of Rhythm down (not an easy task back in the early 90s, when the selection of rap CDs available to a young lad in Calgary wasn’t what it is today).

2. They Reminisce Over You (T.R.O.Y.) – Pete Rock & C.L. Smooth (1992)
Of all the tracks on this mix, none make me feel as nostalgic as this one. Oddly, this track probably made me feel a wave of nostalgia even when I heard it for the first time back in 1992, even though it I had nothing to feel nostalgic about at the time. That’s the feeling producer Pete Rock and rhyme-partner CL Smooth were going for, with “Reminisce” being right there in the title (and breathlessly repeated throughout the song). So when the jazzy horn and bass sample of Tom Scott’s “Today” start playing, and C.L. begins his ode to fallen friend Trouble T-Roy, I’m consistently knocked flat with waves of emotion. There’s a lot of dead homie tributes in hip-hop, and I’d say this one is the best of them.

3. Passing Me By – The Pharcyde (1992)
As a hard-luck high school kid who watched more of his crushes from afar than those that he scored with, I identified with this tale of schoolboy heartbreak a lot. I also listened to the album it was on, Bizarre Ride II the Pharcyde, a lot, more often than most other albums, both because of its greatness and for a more simple reason: I had it on cassette. Instead of buying the CD, I recorded my friend Greg’s copy (freeing me up to spend my money on other CDs). And since I had a Walkman at the time (rather than one of those big, clunky discmans), I ended up listening to things I had on cassette more often than the things I had on CDs, both because I had a long bus commute to high school, and the simple fact that I had fewer cassettes than I had CDs. In 92, I was still a couple years from my first car… which also featured a tape deck. I am old.

4. How Many MC’s… – Black Moon (1993)
Another album I had on cassette. So I had to download it recently, and was pleased to learn that it’s still great. Enta da Stage served as a precursor to the great New York hip-hop that would dominate the mid-90s (along with Dr. Dre’s G-Funk on the West Coast). This track is a more hard-edge than most of the tracks on this playlist, but Black Moon actually did wear backpacks in their debut video, so I guess this isn’t totally out of place. The sparse production reminds me a little of Joy Division in the sombre mood it evokes, which is probably why I still dig it.

5. Soul by the Pound (Thump Mix) – Common Sense (1993)
The Artist Formerly Known as Sense is probably my favourite rapper (although I’m not sure how I feel about Universal Mind Control). He’s become the rapper you love even if you don’t love rap, largely on the strength of his soul-infused Be album. He’s matured considerably since his debut, but this track is still my favourite from his catalogue. It might lack the enlightened approach of later tracks that delved into the declining state of hip-hop, civil rights, or a letter to his unborn child, but you have to love the youthful energy of his unsigned hype phase, where he spit out rapid-fire lyrics over a booming bass track and samples of A Tribe Called Quest, Brand Nubian, and Redman. At the time, this track was a little frustrating, as it represented an awful trend in hip-hop: releasing superior remix versions of songs as singles, leading listeners like myself to buy albums in order to hear those singles, only to be let down by the far inferior album version. Instead, I had to get my fix by watching the video on VHS. Yes, VHS. It was like YouTube with electromagnetic tape.

6. 93 ’til Infinity – Souls of Mischief (1993)
“This is how we chill from 93 ’til…”. Well, it’s already been 15 years, and so far, the Souls of Mischief were right. Cause this jazzy track is still so very chill. Nostalgia story: I won a Rap City contest based on the Souls of Mischief crew the Hieroglyphics. The prize pack included this CD, a Casual comic book, a long-sleeved Hieroglyphics t-shirt and a Hiero logo medallion, which became the first piece of jewelry I’d ever wear. Eventually, it became a thing the girl I was seeing at the time would wear, like it was a letterman jacket or something. With one of those girls, the only way I could figure out that she was breaking up with me (because she was doing a piss-poor job of verbalizing it) was when she handed me the medallion back, which set a light bulb off. But don’t worry, it wasn’t that serious a relationship, so this song brings back no painful memories.

7. C.R.E.A.M. – Wu-Tang Clan (1993)
The jazzy early 90s give way to the gritty mid-90s with the Wu-Tang Clan, who were like nothing else I’d heard when they debuted in 93. RZA’s sparse production picked up from the stripped down beats of Black Moon and added a cinematic scope. Every song felt like it was dipped in grime and darkness, made fascinating by the varied contributions of 10 MCs and their wildly different styles. Enter the Wu-Tang might be my favourite hip-hop album of all-time, and is currently the only one in my record collection.

8. Catch a Bad One – Del tha Funkée Homosapien (1994)
The original Hieroglyphics member, Del changed up his style significantly from his debut with this track, going from a fun-but-somewhat corny style of I Wish My Brother George Was Here to the haunting violin strings and clashing high hats that power this track. In it, the former hippy-esque Del who released the gimmicky “Mistadobalina” lets loose with in-your-face lyrics that assert his place at the top of the emcee hierarchy. It’s interesting that he had to break away from his cousin Ice Cube in order to sound harder.

9. Nappy Heads [Remix Radio Edit] – Fugees (1994)
As annoying as it was to find that Common Sense’s Can I Borrow a Dollar? album didn’t contain the single version of “Soul by the Pound”, it was even worse with the Fugees’ debut album Blunted on Reality, as the Fugees remixed every single they released from that album. And what was left on the album, both singles and non-singles, sucked. Wannabe hard vocals coming from Wyclef Jean, L-Boogie Lauryn Hill, and the other guy just didn’t sound right, especially over the unimaginative production throughout the album, so that was a complete waste of money. Luckily, the remix version of “Nappy Heads” that they released as a single showed a lot more creativity, signalling that the band was one to watch. Their reunion performance of this track was the highlight of Dave Chappelle’s Block Party. (Oh, and yes, I do know that the “other guy” is Pras Michel. I was being funny).

10. Mass Appeal – Gang Starr (1994)
A popular theme of 90s hip-hop was warning against the evils of rap music becoming pop music, and insulting those who crossover (EPMD’s “Crossover” was a late scratch from this list). Oh how times have changed. It almost makes songs like Gang Starr’s “Mass Appeal” sound quaint in a world where the biggest hip-hop artists (T.I., Kanye West, Lil’ Wayne) are also the biggest names in pop music. Maybe this difference helps explain why I switched from hip-hop to indie rock: as it became more popular, hip-hop could no longer fulfil my immature need to avoid listening to things that are popular.

11. It Ain’t Hard to Tell – Nas (1994)
It’s kinda perfect to have this track follow “Mass Appeal”, as Guru’s lyric “maybe your soul you’d sell to have mass appeal” from the above song could easily apply to Nas, who followed up what might be the greatest debut solo hip-hop album of all-time with several diminishing returns. He went from being the heir apparent to Rakim with the street-wise poetry of Illmatic to rapping about money, hoes, and clothes in horrific attempts to go pop. Here, he’s at his best, rapping over a brilliant sample of Michael Jackson’s “Human Nature” with a track that at the time seemed to signal the promise of a new voice, but in retrospect marks the apex of his career.

12. Juicy – The Notorious B.I.G. (1994)

Maybe Nas saw all the dough Biggie was making being both gangsta and commercial, and decided he had to get in on that action. It’s a little odd that this playlist has a song by the Notorious B.I.G., yet none by his nemesis 2Pac, given that at the time, I was firmly in the 2Pac camp. He was my favourite rapper throughout the decade, but his songs haven’t aged as well. Mostly, it comes down to the fact that most of Pac’s songs fail to live up to my number four rule above, whereas exactly one Biggie song (this one) did.

13. I’ll Be There for You/You’re All I Need to Get By – Method Man with Mary J. Blige (1995)
Ah, the hip-hop ballad, the area where many have tried, but only a few have succeeded. Most hip-hop ballads fall into one of two camps: either they’re too earnest and wimpy to take seriously (a la LL Cool J’s “I Need Love”), or they’re too ridiculously hardcore and sexist that they fail as a love song (a la Notorious B.I.G.’s “Me and My Bitch”, which is sampled in this song). Method Man’s remixed “All I Need” (yet again another single that differs from the album track) manages to succeed where most fail, by being sincere without being corny, while maintaining Meth’s street-cred without sounding like a punk. You get the impression that Meth’s boo would actually enjoy having these lyrics written about her.

14. Shimmy Shimmy Ya – Ol’ Dirty Bastard (1995)
I’ve loved this song since it came out, a perfect example of the craziness that made ODB so much fun. But it took Judd Apatow’s Knocked Up to remind me how much. I think I ripped it onto my iPod as soon as I got home from the theatre.

15. Let Me Clear My Throat (Old-School Reunion Remix) – DJ Kool with Biz Markie and Doug E. Fresh (1996)
Depending on when you were born, you might refer to this playlist as “old school”. Which seems ridiculous to me, since the Old School already existed when this stuff was contemporary, but I suppose it’s all relative. To me, old school is stuff like this song (in content if not in date), with party rappers from the 80s like Doug E. Fresh and Biz Markie rapping over infectious DJ beats, encouraging people to jump, or wave their hands in the air as though they are indifferent. Or something like that.

16. Paparazzi – Xzibit (1996)
If this playlist was an attempt to give a full overview of the landscape of hip-hop in the 90s, it would be a miserable failure for the simple fact that the West Coast is way underrepresented. There was a couple Oaktowners early with the Hieroglyphics crew, but that’s not exactly what one thinks of when you think of 90s West Coast rap. Nope, you think of Dr. Dre-inspired gangsta rap, and this is the closest this list gets (featuring production from Tha Alkaholiks rather than Dre). What can I say? As a 31-year-old white dude, the gangsta rap just doesn’t speak to me as it once did. This track manages to make the list because the haunting classical sample of Gabriel Fauré’s “Pavane” (yes, I looked that up). It makes this more than your typical West Coast track, and is yet another entry into the “sell outs suck” meme of hip-hop (brought to you by the guy who went on to host an MTV show).

17. Big Pimpin’ – Jay-Z with UGK (1999)
I had to write “very little misogyny” instead of “no misogyny” mostly because I couldn’t cut this track from the list. It’s probably my favourite Jigga track, and probably my favourite hip-hop track to whistle. The middle-eastern production by Timbaland meshes perfectly with Jay’s vocals, along with the assists from the Underground Kings. I think a big factor for something making this list is if the production is more than your typical hip-hop beats, so “Big Pimpin'” qualifies, despite its more typical subject matter.

18. Ms. Fat Booty – Mos Def (1999)
I finish off with Mos Def, the rapper who was supposed to represent hip-hop’s turn away from the excesses it was suffering through in the late-90s with a more positive, afro-centric approach (similar to that found earlier in the decade). Instead, he reached a small audience and seemed to focus on his acting career more than his music career, while hip-hop got more into excess than before. Oh well.

And there you have it, the best in 90s hip-hop brought to you by a 31-year-old white Canadian guy who doesn’t listen to a whole lot of hip-hop anymore. Do with it what you will. Feel free to suggest omissions, as this might not be my last nostalgia exercise.

List: My Favourite Album for Every Year I’ve Been Alive
Playlist: 18 Great Songs to Appear in Commercials
Top Five Songs from the 90s

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2 thoughts on “Playlist: Best Hip-Hop Songs of the 90s

  1. Pingback: List: The 15 Most Influential Albums of My Life « Critically Speaking

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