The late 90s was a great time to be a teenager.
The X-games was reaching critical popularity, Hip Hop had risen from outsider art to mainstream success, and Donald Trump was only known for cameos in Home Alone 2 and pizza commercials.
The reason I bring up the X-games and Hip Hop is because both had a profound affect on me.
Not just because of who I was, but because of what age I was.
Both skateboarding and 90s Hip Hop are very appealing things to a teenager. Especially a socially anxious teenager, in a constant state of identity crisis with a proclivity for black and white thinking.
What skateboarding values, is the thing that Hip Hop used to: a high-bar for entry and a strict code of ethics.
It was a BIG deal to be called a poser, just as it was a big deal to be called wigger. I couldn’t risk being called either.
But my answer wasn’t to avoid both subcultures, it was to dive in further.
Purity Tests Are Appealing to the Identityless
KRS-One once said you can’t be part of Hip Hop unless you practice Hip Hop, specifically one of the (now) 9 elements.
I took that very seriously (black and white thinking, ahem).
When I was growing up Hip Hop was more like the FDA guidelines for nutrition: 4 basic groups.
I couldn’t dance, I couldn’t afford turntables, I tried tagging and was terrible at it. But I loved writing.
So MC’ing it was.
At that time, I remember there being strict rules (very appealing) about having your own voice or your own style.
Anything less than originality was seemingly punishable by violence.
I took this originality idea, probably, a bit too far.
For me, this meant not sampling a sample that someone else had already sampled.
It even meant that sampling too-popular songs from the past was blasphemous.
I had just “joined” the world of Hip Hop and I was already criticizing Puffy for not passing rigorous purity tests I misinterpreted.
In fact, I was just cribbing the criticisms that Mos Def pointed out on Blackstar’s “Children’s Story”, itself, an updated version of Slick Rick’s song of the same name.
Where Slick Rick was telling a story of a kid on the run from police, Mos Def focused his version on the music industry.
“Me and you kid we gonna make some cash”
“Jackin’ old beats and makin’ the dash…”
They jacked the beats, money came wit’ ease
But son, he couldn’t stop, it’s like he had a disease. He jacked another and another, Michael Jackson, Stevie Wonder
Set some R&B over the track for ‘deep cover’ (187!)
I’ve Learned Better
Long story short, sampling and signifyin’ in music have a long history in black culture.
Signifyin(g) is also a way of demonstrating respect for, goading, or poking fun at a musical style, process, or practice through parody, pastische, implication, indirection, humor, tone- or word-play, the illusions of speech, or narration, and other troping mechanisms… Signifyin(g) shows, among other things, either reverence or irreverence toward previously stated musical statements and values.
The rules about who can use what can feel arbitrary to those on the outside, but to those within the culture, right and wrong ways of referencing past artifacts can feel instinctual.
I say all this to say that teenage-me didn’t know what the hell he was talking about and certainly wasn’t in the position to be gatekeeping anything, let alone, Hip Hop.
So now, with some distance and time between me and my austere teenage self, I want to celebrate the songs that remake the classics, songs so classic as to be almost deemed untouchable, and bring them back to life for a newer generation.
These are songs teenager me would be mad at on principal…while dancing to them and memorizing every word.
Songs That Sample a Blasphemously Popular Song and Justify That Sampling
So, this will mostly just be a list of Old Song vs New Song.
But to make the cut, a song has to at least justify its existence, these songs will get a rating of Justified as signified by a picture of Janet Jackson and Tupac from Poetic Justice:
Then there will be songs that go above and beyond and actually improve on the legacy of the original song they sampled.
These will get a rating of Legendary, signified by a picture of Lawrence Fishburne as Jimmy Jump from King of New York.
Song 1: Tom Tom Club vs Mariah Carey
Mariah Carey’s smash hit “Fantasy” sampled Tom Tom Club’s “Genius of Love”, which I’m told was a party jam before my time.
Mariah’s version is one of the most important songs of my childhood, the 90s, and the history of the world.
That means we’re starting off the list with a: Legendary.
Song 2: The Police vs Puff Daddy, Faith Evans, and 112
I’m not gonna lie, I could rate almost every song on this list as having improved upon its original, mostly because I love hip hop.
But we have to get nitpicky.
While I still get chills and teary eyed every single time (to this day) I hear Faith Evans sings her bridge on “Missing You”, I have to rate this a Justified because Puffy sampled “Every Breath You Take” without asking Sting, so Sting sued him and made 100% of the royalties off of “Missing You”.
Very un-business like Puffy.
Song 3: Foreigner vs M.O.P.
Foreigner’s song “Cold As Ice” peaked at #6 in 1977 on the Billboard charts which is way too high for a song with only one good part.
Luckily for us, M.O.P. sampled that one good part, repeated it over and over, and rapped awesomely on it.
This one is an easy: Legendary.
Song 4: Otis Redding vs Kanye West and Jay Z
I absolutely love “Otis”.
My younger self might have been too idealistic (Kanye made the beat in 20 minutes) to acknowledge how fun this song is, while my older self has outgrown that.
There’s something absolutely exciting about this minimalism of the “Otis” beat, but “Try a Little Tenderness” is a very high bar to clear.
Rating: Poetic Justice.
#5. Pete Rodriguez vs Cardi B, Bad Bunny, and J Balvin
If you were born anytime after 1967 “I Like It Like That” is one of those songs you almost can’t imagine not existing.
Like “Tequila” or every other song on The Sandlot soundtrack, “I Like It Like That” is an anthem that feels foundational to pop music and all that would come after the 1960s.
But after hearing Cardi B’s version, you can’t help but wait for the beat to drop on Pete Rodriguez’s version.
“I Like It” is simply that good.
It also has the added benefit of having 2 choruses. The original Peter Rodriguez part and Cardi’s addictive melody overlaid on top.
2, in this case, is more fun than just 1.
Rating: 1990 Lawrence Fishburne.
#6. Steve Miller and Chip Taylor vs Shaggy and Rayvon
“Life is one big party when you’re still young, but who’s gonna have your back when it’s all done” Shaggy sings on the 2000 “Angel”.
It was the sad-but-fun pop ballad you could belt out at a house party or while driving around your hometown, trying to find something better to do.
This anthem of teenage heart ache actually samples 2 songs.
The underlying music is Steve Miller Band’s, “Joker”.
And the chorus is from Chip Taylor’s “Angel of the Morning” made most famous, perhaps, by Juice Newton in 1981.
Though Shaggy draws heavily from two, separately charting singles, both of which probably make the canon of pop history, he puts enough of his own melody and style into it to make the whole effort worthy of existing.
#7. The Isley Brothers vs Kendrick Lamar
This might the most controversial opinion on this list.
“That Lady, Parts 1 & 2” is such a generationally definitive song, it’s unfair to argue that any song that samples it could improve upon it.
Unfair perhaps, but I’ll give it a try.
American music wouldn’t be the same without the refrain, “who’s that lady”, but what “i” has that its predecessor doesn’t is a vocal edge that matches its blistering guitar playing.
“i” leans into the hazy, sweltering-city-summer sound of the original guitar riff, embodying the “Across 110th Street”-eqsue side of the Isley Brothers classic.
Kendrick’s version, where he talks about inner-struggles (“everybody lack confidence”), battling the devil (“Satan wanna put me in a bow tie, pray that the holy water don’t go dry”) and how, despite it all, he still loves himself, feels almost more in line with the tone of the music, now re-contextualized, than lyrics about a pretty woman.
And I love myself
(The world is a ghetto with big guns and picket signs)
I love myself
(But it can do what it want whenever it want, I don’t mind)
I love myself
(He said I gotta get up, life is more than suicide)
I love myself
(One day at a time, sun gon’ shine)
I gotta go with the King of New York.
#8. Ben E. King vs Sean Kingston
“Stand By Me” may be the most iconic song on this list.
Sean Kingston risked a lot, and had a lot to prove, to justify the existence of a song that samples a civil rights anthem to this extent.
And maybe “Beautiful Girls” found me at the right time in my early 20-something life, but Sean Kingston does just enough catchy-as-hell magic to keep me from balking all these years later.
#9. Kenny Rogers and Dolly Parton vs Pras, Mya, and Old Dirty Bastard
A few years ago, this would be an easy win for Pras and friends.
But it’s a simple fact of life that the more in-your-30s you are, the more you love “Islands In The Stream”.
I didn’t have to exist when “Islands” (justifiably) topped the charts for months, so it never got played out for me.
I did exist while “Ghetto Supastar” was a hit and it still, never got played out for me.
While “Ghetto Supastar” is undeniably a better lyric than “Islands In The Stream”, I can’t call it on this one.
Let’s give it a rating of Janet Jackson + Tupac + Lawrence Fishburne and call it a day.