Hip Hop Hooray: Two More Mixtapes

Hello old friends! It’s already time for another playlist! (What’s that you say? You are still reading the giant tome–literally 5000+ words–I wrote on the last one? Well, I would hate for you to run out of reading or listening material, so on we go!)

As you may have noticed, there was no hip hop on the first playlist. You might have found this strange since our junior high and high school years were right in the midst of the golden age of hip hop. Or you might not have noticed at all because you hate hip hop. If you’re in the former group, read on! If you’re in the latter group, well, I am sorry for you because you are missing out on a lot of great music.


Hip hop is not a genre that is known for worrying too much about clean language. If Tipper Gore were a reader of this illustrious site, she would certainly slap a Parental Advisory sticker on this playlist. If you are offended by swearing or other bad language, or by frank depictions of violence, the second half of this playlist may require some substantial picking and choosing. I won’t feel bad if you skip the second half or if you decide to pass on this altogether.

A NOTE: I think it’s interesting to see how hip hop was developing in this period, so I have arranged both sections of this playlist by track release dates. You’ll see multiple threads in the hip hop world existing at once, so while the playlists are not thematically consistent, they nonetheless accurately reflect what was happening at the time.

ANOTHER NOTE: I’m intending to trim down the commentary on this playlist a little, primarily because the other one took me longer to write than I anticipated. Plus, my kids apparently want me to “read to them” or “make dinner for them”, and Rocket League doesn’t play itself. So, dear reader, you may not need a bookmark for this entry. [Post facto note: I clearly wasn’t serious about keeping this shorter, even though I thought I was.]

PART 1: Good Dance Party Material

Most of this music wasn’t particularly important to the development of hip hop, but it’s just fun; it’s all pretty accessible stuff and generally pretty clean.

YouTube playlist here

Or Spotify:

1. Will Smith – “Parents Just Don’t Understand” – February 17, 1988

I remember lots of kids rapping pieces of this in the halls and entryway of Hillside. I recently watched this video with my kids, who are currently enjoying watching old episodes of “The Fresh Prince of Bel-Air”. That crazy Carlton!

Although I can’t say I’ve ever run off with my parents’ brand new Porsche–heck, I don’t think I’ve ever touched a brand new Porsche–this is still a great song for teenagers. After all, “parents are the same no matter time nor place.

2. Rob Base and DJ Easy Rock – “It Takes Two” – August 2, 1988

This song is one of several that effectively spawned the lame raps of parents and church groups everywhere, using a formula of “I’m [name here] and I’m here to say…”. That said, Rob Base does it with a little more style:

I wanna rock right now
I’m Rob Base and I came to get down
I’m not internationally known
But I’m known to rock the microphone

Plus, the second half of that quatrain gets referenced in the song “Boom” by Fan 3, featured on the “Confessions of a Teenage Drama Queen” soundtrack. So legit.

I remember this song making the cut at a couple of stomps, as well it should–it’s great dance music.

3. Tone Loc – “Wild Thing” – January 23, 1989

Note: the artist’s name is technically “Tone Lōc”, but that’s harder to type, so sorry, Loc.

Tone Loc was huge for about 5 minutes in 1989, popping out “Wild Thing” and “Funky Cold Medina”–the latter of which probably holds the record for being the song of to which the most people know the fewest words.

Along with a couple of my friends–I think Digby and maybe Nate Anderson–I did a karaoke performance of this at Last Blast. Because I’m klassy like that.

4. Young MC – “Bust a Move” – May 22, 1989

This was a song that was clearly written for me: “you’re standing on the wall like you was Poindexter“. I was a Poindexter. I am a Poindexter. I own it.

(Fun fact: the “Poindexter” in question here originates from a nerdy character in the cartoon “Felix the Cat”, not from John Poindexter, a Reagan advisor involved in the Iran-Contra scandal that occurred shortly before this song was released.)

I confess that with too high a frequency, I got “shot down cause ya over-zealous“. Sorry, ladies! I’ve never been anything if not transparent.

This was definitely a different time in music. When was the last time you heard lines like this:

You say, “neat-o”, check your libido
And roll to the church in your new tuxedo

That’s the biz. And speaking of Biz…

5. Biz Markie – “Just a Friend” – September 21, 1989

Most rappers today try to appear completely in control, completely awesome all the time. (Kanye, what?) Even back when this song came out, it was pretty rare for a rapper to be the chump in his own song. Enter Biz Markie.

Who can forget Biz’s stumbling singing, “You, you got what I need but you say he’s just a friend / And you say he’s just a friend, oh baby“?

I didn’t really listen to this song when it came out, but I did frequently by the end of high school. I imagine that I’m not alone in feeling like Biz is sharing a story that’s easy to relate to.

6. MC Hammer – “U Can’t Touch This” – January 13, 1990

Fun fact: MC Hammer was once a batboy for the Oakland A’s. We live in the Bay Area now, and this fact gets a lot of play out here–there was even an MC Hammer night at the Coliseum last year.

It’s easy to think of Hammer as a joke now, but if you think back, you’ll remember that he was freakin’ HUGE when this song came out. Remember when he was hawking BKs while Karl Malone was backing LA Gear?

I remember watching the video to this at Eric Wadley’s house, and seriously considering how great it would be to own some parachute pants. (More time context for you: Eric had taped this video over a recording of Star Trek: The Next Generation.)

7. Bell Biv Devoe – “Poison” – February 24, 1990

This track features one of the most memorable intro beats for any song ever. So great.

Somehow, this song (and a few others, including Black Sabbath‘s Iron Man) made it into very heavy rotation in a several-hour drive to scout camp in the summer of 1990. I think someone had made a mix tape with about 10 songs on it, and it was the only music we had, so I heard this song about 50 times on that trip.

I was just a little too young/immature at the release of this song to truly appreciate how intoxicating the opposite sex can be, but that changed soon enough.

8. Vanilla Ice – “Ice Ice Baby” – July 2, 1990

Of all the songs on this list, for me, this is the one that has the most memories associated with it. A few:

I can still hear Rick Kone shouting:

Kept on pursuing to the next stop
I busted a left and I’m heading to the next block
The block was dead
Yo so I continued to A1A Beachfront Avenue

While we were walking home from Hillside. I think all of our friends learned all the words to this song, but Rick was the first.

Another: My family went on a cruise around this time. They had a bunch of activities for kids, including a karaoke contest. My younger brother Matt, who must have been about 8 years old, decided to perform this song. It was just as awesome as you would expect from an 8 year-old. But my sister Robyn gave Matt the hugest round of applause and I was embarrassed that I hadn’t done so immediately as well. Great lesson for me.

And there are way more than I have time to write. Yeah, Vanilla has had his share of problems over the years. But this song is actually pretty good. And it any time my kids tell me they have a problem, I get the chance to say, “If there was a problem, yo, I’ll solve it!

Word to your mother.

9. Kris Kross – “Jump” – February 6, 1992

The Mac Daddy (James Kelly) and the Daddy Mac (Christopher Smith) were only 13 years old when their album dropped in 1992–in other words, they were just a couple of years younger than us. The album was a huge hit, and this track the biggest hit on it. I just learned that the video of this song sold 100,000 copies on VHS. Crazy.

This song was a constant at stomps at Highland. There were even a couple of kids who tried out the backwards-clothing thing briefly, although that never really caught on in SLC (as I recall). But where the fashion failed, the song was gigantic.

Fun fact: Kris Kross was discovered and produced by Jermaine Dupri, who you may recall from (among other places) his hit 1999 song, “Money Ain’t a Thang”.

Bonus: For your viewing pleasure, we present a classic Kris Kross Sprite commercial.

10. Arrested Development – “Tennessee” – March 24, 1992

Although the phrase “Arrested Development” might be likely to cause you to think of the terrific TV show, the group came first. This collective had a unique sound, particularly when you remember the overwhelming place of gangsta rap in the hip hop world at this time. Their generally positive focus was a dramatic departure from lots of other rap out in this era.

I remember listening to this entire album many times at Elliott Ferris‘s house. I don’t know if it was his or someone else’s, but we just about wore out this album. This song and Mr. Wendal both got constant play on the radio throughout 1992-1993.

Permit me one small moment of religiosity here–perhaps unusual in a rap playlist discussion, I know, but Arrested Development is an atypical group. I love the following line in this song, which Speech directs to God:

I know you’re supposed to be my steering wheel
Not just my spare tire

Although it might cause some of you to think of Carrie Underwood, for me it’s a reminder that a relationship with God is best when it’s not restricted to emergency situations only.

Fun fact: this song takes a sample from Prince, who is known to be a fierce protector of his copyrights. Apparently they didn’t clear that sample with the Artist before using it. He ended up sticking Arrested Development with a bill for $100K as a result.

11. House of Pain – “Jump Around” – May 5, 1992

This is one of the rap songs that I most enjoyed during high school. In retrospect, it’s a pretty pedestrian effort, but it accomplished its goal of getting people to jump around.

Despite not being the most innovative song out there, there were some great lines in this song:

Feelin, funkin, amps in the trunk and I got more rhymes
Than there’s cops at a Dunkin’ Donuts shop
Sho’ nuff, I got props
From the kids on the Hill plus my mom and my pops

You’ve got to like a song that hits the well-worn rap references of big amplifiers and cops at a doughnut shop, and then somehow mixes references to Cypress Hill and the rapper’s PARENTS in the same line. From the most expected to one of the least in the same verse.

Every time this came on at a dance or stomp, I’d do my best to find Digby and rap the whole thing. Incidentally, one of Rick’s sisters–either Angela or Kristina–transcribed this song from a recording for me. Awesome.

12. Sir Mix-A-Lot – “Baby Got Back” – May 7, 1992

Few songs get right to it like Mix-A-Lot’s classic:

I like big butts and I can not lie
You other brothers can’t deny
That when a girl walks in with an itty bitty waist
And a round thing in your face
You get sprung

So coy, Mix-A-Lot. So subtle.

That said, this song is and has always been infectious. It’s not one that I would have put on at home–not sure how the padres would have received it–but it’s as awesome now as it ever was.

I heard that Steve Nelson and The Piano Guys are doing a version of this song soon. Hope that intel is correct.

Reminiscence: There’s a classic episode of “Friends” where Ross discovers that singing this song to his new baby that makes her laugh. Rachel is initially very dismissive, but soon discovers that it’s true. Everybody likes Mix-A-Lot. And Friends always reminds me of Scooter, Garth, and Digby.

Another: I’m pretty sure that I heard this song at every wedding I attended in Chicago during our 7 years there. Those midwesterners love it. And that makes me love them even more.

13. Wreckx-N-Effect – “Rump Shaker” – August 25, 1992

Another song about butts? Yes! And there are more on this list! This was probably the biggest cultural moment for posteriors until Meghan Trainor and many others in 2013 and 2014.

Just in case you found Mix-A-Lot too subtle, Wreckx-N-Effect wanted to make sure you didn’t have to dig through any unnecessary euphemisms. They also get right to the point from the very beginning:

All I wanna do is zoom-a-zoom-zoom-zoom
And a poom-poom – JUST SHAKE YA RUMP

And it only gets less subtle from there. This song was also in constant rotation on the radio, but I don’t remember it getting played at any church dances. :)

Fun fact: Pharrell helped produce this song. I’m pretty sure I didn’t hear about him until at least 15 years after this, though. His “Happy” is one our family favorites now, though, and always good for starting up a dance party at our house.

14. Positive K – “I Got a Man” – December 1, 1992

By far the biggest hit of Positive K’s career, this song is the age-old story of a guy trying to convince a girl with a boyfriend to choose him instead. It doesn’t work.

Naming no names here, but I confess that there might have been a time or two when I really wanted to convince a girl that her current boyfriend was no good and she should choose me instead. But I always chickened out. At least K gave it a try.

Fun fact: this song samples a bunch of other songs–and in turn got sampled by our man Jermaine Dupri.

15. Snow – “Informer” – January 2, 1993

Back to the white rappers! Like Vanilla Ice, Snow just went right ahead and owned it with his name. There was a lot of this going on at the time. Remember the basketball player Jason Williams, nicknamed White Chocolate? I do confess that Snow’s name is particularly appropriate given the fact that he is from Canada.

(Did you think he spent time in Jamaica? Me too! But as far as I can tell, he did not. He picked up the the reggae influence and style from neighbors in Toronto.)

Everybody pretended to know the lyrics to this song when it came out. In reality, it was more like, “Informer! uh….., a licky boom boom down!

I will pay $20 to see anyone perform this at the reunion–but you have to actually know the words.

16. 95 South – “Whoot, There It Is” – March 22, 1993
17. Tag Team – “Whoomp! There It Is” – May 7, 1993

These two are presented, appropriately, as a tag team. As you may recall, these two songs came out almost right at the same time. Although they claim otherwise, it’s a virtual certainty that Tag Team knew about the 95 South song. Still, Tag Team‘s version became the more popular and enduring of the two.

These two songs continued the booty mania mentioned earlier. In fact, 95 South in particular seemed to have one-track minds, releasing songs like “Do the Booty Hop” and “Heiny Heiny”.

Although both songs have their appeal, it’s the Tag Team version that I remember best. I still hear it on the radio, and it takes me right back to 1993. I remember hearing this song on the radio frequently that summer, and always loved singing along to the beginning:

Tag Team, back again
Check it to wreck it, let’s begin
Party on, party people, let me hear some noise
DC’s in the house, jump, jump, rejoice
Says there’s a party over here, a party over there
Wave your hands in the air, shake your derierre
These three words mean you’re gettin’ busy:
Whoomp, there it is!

Also appropriate for our reunion are the lines that I most often quote today:

I’m takin’ it back to the old school
Cause I’m an old fool who’s so cool
If you wanna get down, I’mma show you the way
Whoomp, there it is! Lemme hear ya say …

Note: Spotify doesn’t have the 95 South track, so I omitted it.

18. Salt-N-Pepa – “Shoop” – September 21, 1993

I remember listening to this song while dragging State St. with Raleigh Smith. I’m sure I didn’t appreciate it as such at the time, but this song is delightfully liberated, which was fairly typical of rap by women in this time period. (General discussions of sexuality aside, I think it’s fairly uncontroversial to say that equality between the genders in owning their own desires is positive.)

Plus this song makes references to “Annie“, “Scooby Doo“, and “Prince“. What’s not to like?

19. Coolio – “Fantastic Voyage” – March 8, 1994

This song always makes me think of Cade Strate. (Fee, dude, you need to come to the reunion!) Although definitely not as famous as Coolio’s “Gangsta’s Paradise”–which was included on the soundtrack to “Dangerous Minds” with Michelle Pfeiffer–this song is one that more reminds me of high school.

We did a lot of cruising around looking for people in high school. (Aside: with the ubiquity of cell phones today, I don’t think this happens to nearly the same degree anymore. Too bad for today’s kids.) Although we didn’t have a ’65 like Coolio, we did have Scott’s Silver Bullet, Digby’s Jeep, Elliott’s Accord (with Satan-powered heat), and Raleigh’s Blue Boutique, among others. There were a lot of great times just cruising around with no end point in mind–some of my favorite times in high school, in fact.

Coolio presents a inclusive party here–he tells us that “Ain’t no bloodin’, ain’t no crippin’“, and “it really don’t matter if you’re white or black“. The video emphasizes the same, with all kinds of people coming out of the trunk. Plus this song has some amazing references–most obviously the sci-fi film of the same title, but also Diana Ross, the incomparable Nas, the Bible (2 Thessalonians 3:10), and even Harry Truman.

20. Montell Jordan – “This is How We Do It” – February 6, 1995

I cannot think of this song without thinking of Raleigh’s brother, Jordan Smith. He had this song and other hip hop classics memorized and would perform them with some serious panache. I hope that hasn’t changed!

Like Coolio, Montell Jordan is inviting everyone to this party:

This is how we do it, all hands are in the air
And wave them from here to there
If you’re an O.G. mack or a wannabe player

And this is how I hope our reunion will be. I hope to see you all there. “To all my neighbors, you got much flavor.

PART 2: Real Deal Holyfield Golden Age Material

NOTE, AGAIN: For real, if you have a problem with bad language, imagine Dante’s sign from “Inferno” above this playlist:

You have been warned.  I no longer bear any responsibility for your sensitivities.

YouTube Playlist here

Or Spotify:

1. Run DMC – “It’s Tricky” – February 8, 1987

This song, along with Beastie Boys“Fight For Your Right to Party”, was my introduction to hip hop. There’s no question that Run DMC was hugely influential in the popularization and development of hip hop; they get named-dropped and otherwise referenced all the time by other artists (including in Black Eyed Peas recent track, “Yesterday”). I had no context for that when I first encountered this song in late elementary school or early junior high, though; it was just a very different sound than the music I was generally listening to at home or with friends.

I know that Rick Kone and Eric Wadley introduced me to Beastie Boys; I believe they also introduced me to this song. At any rate, hearing this song planted a seed in my brain that has slowly but steadily grown ever since.

2. NWA – “Straight Outta Compton” – August 9, 1988

At Hillside Junior High, Mrs. Summerhays taught glee class. She had a truly astounding ability to whip a bunch of incredibly badly-behaved boys into a cohesive enough choir to perform “Goodbye My Coney Island Baby” and “The Little Old Lady from Pasadena” for our parents. She ruled with an iron fist, which was completely necessary. But she sometimes got laryngitis and had to be out for a couple of days.

When she was gone, we had substitutes, and the subs simply had no way to contend with the chaos that naturally resulted from 50+ adolescent boys who were boiling over with a need to cause mischief. I remember one kid tricking a sub into putting on a 2 Live Crew album for a short period of time. That didn’t end well.

On one occasion of Mrs. Summerhays’s absence, somebody brought in a copy of NWA‘s “Straight Outta Compton” on a Walkman, and I listened to this track. I remember feeling very guilty about it, but also feeling like I had discovered something amazing and foreign and vaguely important (although it’s possible that my recollection has been modified somewhat by retrospection). But I definitely knew that this was a totally different kind of hip hop than I’d ever heard before. It was angry and raw and completely separate from the little I’d been exposed to at that point; in a lot of ways, this felt more different from Run DMC than Run DMC did from the pop music I’d known before.

I never bought this album–or nearly any hip hop–in high school, but it’s an album I’ve listened to a number of times over the years. Whenever I hear this track, it still unearths that sense of finding something totally new for the first time. I doubt this song ever made it in a glee performance, though.

3. Public Enemy – “911 Is A Joke” – March 22, 1990

I remember Jared Robinson recommending Public Enemy to me in high school, and this song in particular. Flavor Flav was crazy (and continues to be crazy), and the whole clock-wearing or car-hood-ornament-wearing thing was so over the top. (Do you remember kids stealing the hood ornaments from every car around? I can sort of understand the attraction of having a Mercedes ornament, but someone once ripped the ornament off our Dodge Caravan. What the what?)

This song was shocking to me–or at least it was shocking to learn that 911 response time was abysmal in poor neighborhoods. NWA and others talk about their art being a reflection of their reality; this song clearly articulates that reality in a way that makes the segregation of communities and the services they receive abundantly apparent. As is true with many songs on this list, I had no personal reference to understand this track, but it nonetheless opened my eyes to what many other people experience.

4. LL Cool J – “Mama Said Knock You Out” – September 14, 1990

Any time the word “comeback” gets used in practically any context, my immediate reaction is to say, “Don’t call it a comeback, I’ve been here for years!

I have always loved the braggadocio of this song. How can you not appreciate the confidence of a guy whose name derives from “Ladies Love Cool James” and who spits “I’m gonna take this itty bitty world by storm / And I’m just getting warm“? It’s great. It takes the confidence of NWA but generalizes it completely, making it much easier to digest–for better or worse. There are tons of songs in this same vein, but this is one of the best.

My strongest recollection of this song is some guy playing it on a boombox in the parking lot of the Taco Bell at 21st and 21st, probably in the summer of 1991. I’d heard it before that, but something about hearing it outside when I was walking around with my friends and feeling like life was pretty good seared it into my brain.

5. Del Tha Funkee Homosapien – “Mistadobalina” – October 22, 1991

Fun fact: the titular character from this song–a certain Mr. Bob Dobalina–is a reference to a Monkees song, Zilch.

Fun fact number 2: Del the Funkee Homosapien is the rapper on the awesome Gorillaz track, “Clint Eastwood”. I only learned that recently, despite having listened to that Gorillaz song dozens of times. Also, the Monkees/Gorillaz combo here is delightful.

Fun fact number 3: Del is the cousin of none other than Ice Cube. No kidding.

This song is primarily here because it’s so dang catchy. It’s perhaps not Del’s greatest work, but it gets the people goin’! In comparison to the gangsta rap that was really hitting its stride around this time, the concerns expressed in this track are both tamer and more widely understandable:

Friends can be fraudulent, just you wait and see
First he was my moneygrip, then he stole my honeydip
Mista Dobalina is a serpent, don’t you agree?

It almost seems cute compared to Ice Cube’s lyrics from the same era. When people think of hip hop from this era, they sometimes forget that it wasn’t all East Coast/West Coast feuding–there was plenty of work like this.

I somehow completely missed this song when it came out, and didn’t pick it up until I heard it at the Sigma Chi house in college. Still, it reminds me of this era so clearly that it might as well have been a song I knew at Highland.

6. Eric B. & Rakim – “Don’t Sweat The Technique” – June 23, 1992

Aside: You know what? I COMPLETELY didn’t follow through on my promise to keep it brief. This one is WAY longer than the first playlist commentary! Where’s my editor? Amateur hour here.

OK, back on track: Eric B. & Rakim were extremely important to the development of hip hop. Rakim is widely considered to be one of the greatest MCs of all time, and his complex rhyme schemes influenced a huge number of aspiring rappers. This is a classic track, and one that I remember listening to on the radio junior year with regularity.

7. Das EFX – “Mic Checka” – July 16, 1992

The style this song is phenomenal. And the number of cultural references is off the hook: Gladys Knight, Wonder Twins, Bamm-Bamm, Daddy Warbucks, Rocky, Boomer Esiason, Peggy Fleming, Hawaiian Punch, The Captain and Tennille, Uncle Fester, and on and on. This song is a serious treasure trove of references to our generational experiences.

8. Digable Planets – “Rebirth of Slick” – November 9, 1992

At my house, there were very few TV shows that were explicitly on the “not allowed” list, but after one or two shows hit that list, I became more careful about what I risked putting on in the family room. One show that I watched quietly in the basement was “In Living Color”, as I suspected that the humor might not resonate well with my parents.

That show had lots of great musical acts on it, as well as the Fly Girls. One of those musical acts was Digable Planets, and they performed their big hit, “Rebirth of Slick (Cool Like Dat)”. Although Doodlebug got cut off at the end of the show, it was still a great performance that I couldn’t get out of my head. Plus, it featured a young Jennifer Lopez dancing in the background!

I also remember hearing this song while sitting in Clark Whisenant’s Land Cruiser at Rainbow on 21st and 21st, getting gas. I felt “chill like that” the whole night after that.

And of course, Digable Planets were right when they predicted: “the babes’ll go spastic / hip hop gains a classic.” This is indeed a classic.

9. Dr. Dre – “Nuthin’ But A ‘G’ Thang” – November 19, 1992

Speaking of classics, there are few tracks as iconic as Dre’s “Nuthin’ But A ‘G’ Thang”. I listened to this song many times in high school–always the radio edit, since I wasn’t buying any rap music at the time–and surely more than 100 times since high school. My brother Matt and I always enjoy a good duo performance of this and other Dre/Snoop songs, although we generally perform the extra clean version, where even some non-offensive language is replaced for good measure.

Sometimes people complain about Dre’s writing cred. They might even have a point on this track, where Dre doesn’t necessarily bring his best rhymes:

Well I’m peeping and I’m creeping and I’m creep-in


Never let me slip, ’cause if I slip, then I’m slippin’

That’s just lazy, Dre.  Snoop shines by comparison:

Fallin’ back on that ass, with a hellafied gangta lean
Gettin’ funky on the mic like an old batch of collard greens
It’s the capital S–oh yes I’m fresh–N double-O P
D O double-G Y D O double-G you see

But the truth is that Dre is and has always been a producer more than an MC (although he claims otherwise when he says, “You never been on a ride like this befo’ / With a producer who can rap and control the maestro / At the same time with the dope rhyme that I kick“). His production here and elsewhere–look at other true classics like “Still D.R.E.“–is beyond compare. Good rhymes, yes–but the production is the real reason I loved this song in high school and ever since.

Note: Spotify doesn’t have this track–or any Dre before 1999–so I substituted Still D.R.E. in here.

10. Wu-Tang Clan – “Protect Ya Neck” – December 14, 1992

Wu-Tang is a real murderers row of amazing hip hop talent. From Redman and Method Man to ODB and Raekwon, Wu Tang has been a force to be reckoned with ever since their seminal “36 Chambers” came out. There’s no question that this collective was a major force in shaping hip hop for many years to come.

Truth be told, I didn’t listen to much Wu-Tang back in high school. But listening to this song instantly transports me to its time period.

11. Naughty By Nature – “Hip Hop Hooray” – August 24, 1991

Digby knew all the words to this song. I remember him performing bits of it in my front yard. Of course, without the luxury of the internet to get lyrics, or even liner notes since none of us owned this album, the only way to gain that knowledge was to listen for it on the radio and then record it on a tape player–or just listen to it on the radio enough times to memorize it. Hard-earned knowledge.

Naughty By Nature had some very memorable songs, and this is one of the most well known (possibly just behind O.P.P.).

It’s a love song for hip hop.

I live and die for Hip Hop
This is Hip Hop for today
I give props to hip-hop so
Hip Hop Hooray

With songs like this and The Roots Act Too (Love of My Life) and lots of others, there are so many great odes to hip hop out there. This was the first one I ever heard.

12. Ice Cube – “It Was A Good Day” – February 23, 1993

It’s a little weird for me to see Ice Cube (AND Ice T) playing a cop in movies. Or even a barber. Or whatever. Back when this song came out, Ice Cube and his compatriots were among the most feared people in America. This bleak depiction of a life where a good day was marked by getting drunk early in the morning and not having to shoot anyone was totally beyond my comprehension.

Combined with his performance in “Boyz N The Hood”, this song told me everything I needed to know about Ice Cube–he was completely legit, and hard as [radio edit]. Like all great art (feel free to take issue with my characterization), this piece showed me something from the artist’s unique perspective and caused me to consider my own place in a world that was so drastically different than my own. I felt that way looking at “Saturn Devouring His Son” or seeing “Les Miserables” or watching “Spirited Away” for the first time–the complete otherness was fascinating and thought-provoking. I don’t now and never have related to this song at all, and yet I clearly hear Ice Cube–which is a big part of what makes it so great.

13. Cyprus Hill – “Insane in the Brain” – June 22, 1993

You always know if you are listening to Cyprus Hill–their style and voice is immediately recognizable (almost to the same degree as Snoop or Red Hot Chili Peppers or The Doors). And this song is no exception.

You know how songs sometimes have a clear place association in your mind? Well, for some reason, this song always takes me back to 13th East and 21st South, by KFC and that self-wash car wash. I was sitting in my car at the light one day in 1993 or 1994 when this came on, and I thought it was amazing. I’m still not sure what membrane is being referenced, but I also don’t care.

14. A Tribe Called Quest – “Award Tour” – November 1993

There are few albums as good as A Tribe Called Quest’s The Low End Theory–but Midnight Marauders gives it a run for its money. And Award Tour is unquestionably the best song on a great album.

There is some serious skill applied to this track. Take Q-Tip‘s first verse, where he talks about the brand of steering wheel Formula 1 drivers use (“See, lyrically I’m Mario Andretti on the MoMo“), whips out some geometry with a dose of wordplay (“Who can drop it on the angle, acute at that“), and references scat singing (“So, do that, do that, do do that that that“), an important predecessor of rap. That’s pretty tight.

I remember walking out into the Highland parking lot after school one day and someone had this track playing loudly from their car, out near the corner of 21st and 17th. I remember thinking it was pretty rad. Subsequent revisitation has only convinced me that I had no idea how good it really was.

15. KRS-ONE – “Sound of Da Police” – December 6, 1993

I’ll be honest: KRS-ONE is not an artist to whom I’ve spent a lot of time listening. I couldn’t name many of his tracks, and would know almost none of his lyrics cold. No special reason; I just haven’t really gotten to know him. That said, I liked and still like this track. It’s very much in the same vein as some NWA songs in skepticism of a police force that may not have the interests of all citizens equally in mind, as made clear in its insinuation that cops may be complicit in drug dealing.

Plus, this song uses the line “I’d rather say ‘see ya’ cause I would never be ya”, a reference to 1991’s “New Jack City”. I remember Scott Thomas using a similar line during freshman gym after he crushed a home run in softball.

16. Snoop Doggy Dogg – “Gin and Juice” – January 15, 1994

I am confident that this track would make playlists for many of our classmates. For me, it is forever associated with Raleigh Smith‘s beast of a car. (Early 70s, maybe a Pontiac? I’m not sure. But it was huge. And looked like a gangsta car. Which caused po-po problems for Scott and Raleigh, as it turned out. Ask them for the story.)

I learned a lot from this song–mixed drink recipes, the definition of “Indo”, that Snoop valued short-term physical companionship above long-term love-based relationships, and so much more. Plus, it’s another great Dre production.

Snoop’s impossibly mellow flow is on masterful display here. I’ve never listened to another rapper who, even at high speed of lyrical delivery, sounds so placid, so unhurried. It’s a good way to be.

17. Beastie Boys – “Sabotage” – January 28, 1994

I can’t stand it, I know you planned it
I’m gonna set it straight, this Watergate

The shrill opening lines from Ad-Rock and bass guitar-backed beat set this track up as the polar opposite of “Gin and Juice”, which was released less than two weeks earlier. The video for this song is frantic, while Snoop’s is completely in control. This time in hip hop history was one of broad experimentation, and the vast gulf between “Gin and Juice” and “Sabotage” shows this in spades.

This song appears on the “Ill Communication” album, the first hip hop album I ever bought. Props to Digby and Eric for first introducing me to Beastie Boys in about third grade.

18. Nas – “N.Y. State of Mind” – April 19, 1994

What, you were thinking of the Billy Joel song? Not in my house! Or at least not on this playlist.

Not too much to say about this one–it’s one of the core tracks on an album that is generally considered to be the greatest hip hop album of all time. In writing this, I even learned that the lyrics are featured in the Norton Anthology of African American Literature. Pretty great.

19. Warren G – “Regulate” – April 28, 1994

Jordan Smith completely owned this song–I think his performance was even better than Nate Dogg‘s. When we were playing basketball at Raleigh‘s house, Jordan regularly put this one and proceeded to regulate.

This song tells the story of Warren G and Nate Dogg getting into, and out of, trouble before finding some girls. Nate Dogg “generously shares with Warren G the credit for neutralizing the situation, though clearly Nate Dogg did all of the hard work”, one astute commentator mentions.

You gotta love the g-funk, and Nate Dogg’s signature song only gets better with age (like so many of our classmates).

20. Common – “I Used To Love H.E.R” – September 27, 1994

High school is a great time for people to fall in love with something–writing, math, volleyball, guitar, whatever. So many people find their passion(s) in those years. I’m looking forward to seeing how many of our classmates continued with their passions after Highland! Is Kori still in love with drama? Is Rosie still producing great art? Is Jared still a butt rocker?  Is Dave Ward still the president?

One of the best known “conscious rappers“, Common was always clearly in love with the genre as well as the message. This song almost sounds like a love song about a girl, but turns out to be an ode to hip hop. He calls out a lot of rappers who seem to have lost the truth of the genre:

Now I see her in commercials, she’s universal
She used to only swing it with the inner-city circle
Now she be in the burbs, looking rock and dressin’ hippie
And on some dumb shit, when she comes to the city
Talking about popping Glocks serving rocks and hittin’ switches
Now she’s a gangsta rolling with gangsta bitches

He clearly wouldn’t have been thrilled with suburban me appropriating hip hop for myself–but notably, he also decries those who make rap into nothing more than glorification of the gangsta lifestyle. Good thing you can’t see my “Thug Life” tat when I have my shirt on.

21. Notorious BIG – “Big Poppa” – February 20, 1995
22. Tupac – “Dear Mama” – February 21, 1995

Although each of these songs merit their own lengthy entry, I am super tired of writing. Also, these two rappers often find their narratives intertwined, and also find themselves listed together atop rankings of the greatest rappers of all time, so sticking them together seems OK.

In truth, Biggie and Pac are as different as they are similar, as evidenced by these tracks. Listen to them both. Although the titles might sound similar, they are exceptionally different in flow, tone, and message. They were released within a day of each other and yet sound years apart.  They are opposite poles of a hip hop divide that would eventually lead to the death of both artists.

I spent plenty of hours listening to both of these artists around the end of high school and into the following year. I always liked 2Pac more than Biggie. Some of you may feel the opposite. But I hope that whatever differences we have–even big ones like East Coast/West Coast–can be bridged by our commonalities. Let’s all come together.

Thanks for reading. And thanks for everything that all of you have done for me over the years–either directly or through your influence. To quote Pac:

And there’s no way I can pay you back, but my plan
Is to show you that I understand
You are appreciated