The Top 40 of the Top 40 of the 1990s, 40-31

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October 15, 2015 by billysparrow

So, earlier this year, somewhere in the midst of listening to either the 80s on 8 or 90s on 9 weekly countdown on Sirius XM, I had an idea. Generally, I have lots of ideas and/or questions while listening to these shows, like “How was there so much terrible R&B in the 1990s?” or “Stars on 45 was really a thing?” or “What is Henry Lee Summer doing these days?” But, for the purposes of this blog, I’m going to focus on one particular idea I had. We can explore other topics–those above and many others–at your leisure.

The idea of which I speak is trying to come up with the Top 40 of the Top 40 of the 1980s and 1990s. That is, my personal 40 favorite songs of those songs that charted in the Top 40 according to the weekly Billboard Hot 100 in each of the two decades.

To answer the obvious questions:

Yes, I am single.

Yes, I probably have too much free time.

No, I can’t think of anything better to do.

The initial compiling was made easier by the discovery of John Michaelson and Jarrett Nolan’s Weekly Top 40 website, which lists the weekly Top 40 for 1955-2000. I probably would’ve still proceeded with this endeavor without the website, but its existence assured that I would have free time for more important things, like watching marathons of “The Facts of Life,” “Celebrity Bowling,” and “Bar Rescue.” So thanks, fellas.

Now, I will obviously be doing a different Top 40 for each decade, because if I combined them into one Top 40, there’d be maybe three songs from the 1990s. I’m not saying the 1990s was a weak decade for music; I’m writing it. If you’re reading this out loud, I guess you’re saying it. But that’s on you.

Anyway, my task for the 1990s countdown was made easier by the discovery that 95% of the cool songs I liked in the 1990s never actually charted in the Top 40. For instance, by the number of times I heard “The Way” by Fastball in college, I would have thought that song was #1 for several weeks. Never cracked the Top 40. The inferior “Out of My Head” was the only Fastball song to chart. And that’s one more song than The Wallflowers had, which I still find amazing. However, there was one song I love that I would’ve never thought charted. We’ll get there eventually.

For now, we’ll start the 1990s countdown with numbers 40 to 31, represented by YouTube videos of the songs (unless Prince sang them, in which case you’ll just have to sing them in your head). Each Thursday will bring another 10 until we’re all done. And in the last one I’ll give you 100 to 41 (minus the YouTube links), so you can see that I’ve taken this task seriously and that, um, I’m a lunatic, I guess. And then I will move on to the 1980s, which, right now, IS MELTING MY BRAIN! TOO MANY SONGS! TOO MANY CHOICES! HELP ME!

OK then, here goes My Top 40 of the Top 40 of the 1990s. Feel free to agree or disagree. But those who agree will be respected much, much more.

40. Lord Tariq and Peter Gunz, “Deja Vu (Uptown Baby)” [Peaked at #9, 3/28/98]

I’m a sucker for a good New York City song. And, yes, I’m calling this a good New York City song, despite the fact that it takes almost the whole song until Staten Island gets a shoutout (not in the video, so just trust me). But at least it gets mentioned before Long Island. And, yes, that is Shea Stadium in the video, and that was definitely not in the Bronx.

Also, I did not know that the musical hook is taken from a Steely Dan song (“Black Cow”), because my Steely Dan knowledge is light. In fact, they’re making the money from the song, because they sued for copyright infringement and won. So I guess this is now my favorite Steely Dan song.

And please know that whenever I have to go uptown anywhere, I say “Uptown, baby” in my head. Or maybe I’m saying out loud.

39. Digital Underground, “The Humpty Dance” [Peaked at #11, 6/2/90]

This was hanging in the low 40s earlier today, but then I came to my senses and moved it up to #39. There’s just too much good here to leave it out. It should be in only for “Yo, fat girl, come here/Are you ticklish?/Yeah, I called you fat/Look at me I’m skinny.” And, yes, listen to that bass groove.

Sure, it is a completely stupid song, but, SPOILER ALERT, it won’t be the last stupid song in my Top 40. Sometimes the stupid songs have it all over the smart ones. Actually, most of the time they do.

38. Pras featuring Mya and Ol’ Dirty Bastard, “Ghetto Supastar (That Is What You Are)” [Peaked at #15, 8/8/98]

I am a sucker for soundtrack songs, but (a) I’ve never seen “Bulworth” and (b) I’d like this song even if it wasn’t on a soundtrack. The “Islands in the Stream” echo is much appreciated, and, as always, adding Ol’ Dirty Bastard to anything makes it better. There’s no attribution for this on Wikipedia, so maybe it’s not true at all, but I like the idea of it anyway:

“According to Pras, the song was originally to be a collabaration [sic] between himself and Mya. Ol’ Dirty Bastard was in the same building, recording another entirely different song and mistakenly burst into the studio where Pras and Mya were setting up, leading Pras to invite him to be a part of the song.”

Ol’ Dirty Bastard, you are missed.

37. Coolio, “1,2,3,4 (Sumpin’ New)” [Peaked at #5, 5/4/96]

Sometime in the last few years, I came to this interesting realization: I think I like Coolio. Or, at least, I like the Top 40 hits Coolio had. At the time his songs were on the radio, I don’t think I gave him a second thought (I liked “Gangsta’s Paradise” well enough), but here in the 2010s, I’m a Coolio fan, I guess, though he lost me a little on his episode of “Celebrity Wife Swap.”

Anyway, at the risk of losing all the Coolio fans who planned on checking every installment to see where the other Coolio songs ranked, I will reveal that this is the only Coolio song in the Top 40 (two others are in the Top 100). It’s got the best groove of the three.

And, as a bonus, here’s Coolio singing the song with the Muppets.

36. US3, “Cantaloop (Flip Fantasia)” [Peaked at #9, 3/5/94]

Speaking of a solid groove, here’s another winner. It’s one of those songs that it’s hard to imagine became a hit. It just seems too good to be popular. That doesn’t make any sense, does it? So be it.

If I were ever to do a Top 40 of One-Hit Wonders, I’m pretty confident this would chart pretty high. But I’m not doing that. I gotta have a life here. Get off my back!

Through the first five, I seem much less white than I am. That will end soon. Also, I appear to have a fondness for songs with parentheses.

35. Chumbawamba, “Tubthumping” [Peaked at #6, 12/6/97]

Hey, look, another great one-hit wonder! What’s that you say? This song isn’t great? It’s stupid and annoying? Well, maybe you’re stupid and annoying? Did you ever think of that?

Oh, c’mon, baby. I didn’t mean it. Don’t leave. Come back. Let’s drink a whiskey drink. And then a vodka drink. And then a lager drink. And then a cider drink. We’ll sing the songs that remind us of the good times, and then the songs that remind us of the best times.

See, that’s better.

34. Prince, “Cream” [Peaked at #1, 11/16/91]

Sorry, Prince hates YouTube. So just sing it to yourself. Or call me and I’ll sing it for you. Sure, that’ll be weird. But not that weird. If it is in fact true that Prince wrote this song while staring at himself in the mirror, it won’t be any weirder than that.

“Cream/Sh-boogie bop.” I don’t know why that’s great. It just is.

33. Ini Kamoze, “Here Comes the Hotstepper” [Peaked at #1, 12/24/94]

When I first started putting this list together, I was pretty convinced that a current listen to this song would prove that it didn’t hold up. I was mistaken. It is just as good as ever. Another stellar one-hit wonder. And I think if everyone approached a police officer by saying “Excuse me, Mr. Officer” (or Mrs. Officer if appropriate…sorry, Miss and Ms. don’t work syllabically) in that exact cadence, our police/community relations would really improve.

If I had any shame left, I would be ashamed to admit that it wasn’t until the initial current listen that I finally realized that they’re saying “Murderer” in the chorus. I think I thought they were saying “Word it up,” which makes absolutely no sense and proves that I am very, very white.

32. Jewel, “Foolish Games” [Peaked at #2, 5/10/97]

Look, I have Jewel bootlegs on cassette. I’ve also seen her in concert more than once (one time Matt Pinfield gave me a ticket outside of Irving Plaza; if I thought a Matt Pinfield story would dazzle you, I’d tell you the whole tale, but I think we can agree to just leave it at that). And I have her book of poetry signed. I’m OK telling you all that.

Sure, I thought/think she’s quite attractive, but I do think she has good songs and a great voice. And this is my choice for the best of her Top 40 hits. Judge me if you wish. Just know that if you do, I am never dubbing you copies of those bootlegs.

31. Spin Doctors, “Little Miss Can’t Be Wrong” [Peaked at #17, 12/26/92]

I spent a healthy amount of time (which is to say no more than a few hours) trying to first distinguish between this and “Two Princes” and then deciding which one I liked better. I’ve already spoiled enough by saying that there are no more Jewel or Coolio songs in the Top 40, thus alienating that vast readership, so I will not reveal if “Two Princes” appears later in the countdown. Let that mystery haunt your dreams.

I will say that, for whatever reason, “I hope those cigarettes are gonna make you cough/I hope you hear this song and it pissed you off/I take that back, I hope you’re doing fine/And if I had a dollar, I might give you 99” makes me happier than it probably ought to.

This also almost certainly sounds better while not watching the video.

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3 thoughts on “The Top 40 of the Top 40 of the 1990s, 40-31

  1. […] previous 10 can be found here, in case you need a reminder or you just want to reread it and have your mind blown […]

  2. […] Bottom 20 of the Top 40 of the Top 40 of the 1990s can be found here and […]

  3. […] Top 40 of the Top 40 of the 1990s here, here, and […]

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