1)Cher, “Believe”
SONG: I’d like to say that this is a case like Aerosmith’s “I Don’t Wanna Miss A Thing–that is to say, where years and years of people hating the song have made me forget that if I were hearing it for the first time it might not seem like such a piece of shit, but two things nullify that argument right away. One nullification comes from the Curse Of Nineties Irony–I can distinctly remember people making terrible fun of this song, and Cher herself, the week the song came out, which would have been in October 1998, not 1999. This was a phenomenon that I somewhat doubt existed prior to the irony-drenched 1990s. The second and more obviously effective nullifier concerns her voice–of course the Auto-Tune sounds like shit nowadays and probably sounded like shit before it became one of the most hated devices in pop, but the parts where she has to belt the high notes make her sound deep and manly. I could also bring up a third nullifier, which is that the backing music is just a simple plunked-synth line and an even simpler preprogrammed beat, but maybe we should be happy that she didn’t spend her money on anything even worse.
VIDEO: Cher parties in a club with people 35 years her junior. This was probably the beginning of celebrities past the age of 50 Botoxing themselves so that you could no longer even guess how old they actually were. A girl who looks more like Natalie Portman than Portman herself walks around a stuffed, green-lit club sporting Drew Barrymore’s pageboy hair from Scream and feels sad, then Cher for some reason switches place with her.

2)TLC, “No Scrubs”
SONG: I suppose I could give them the chorus. It’s held up, right? Do the kids today know it?
VIDEO: They’re in some zero-gravity silver metal science-fiction corridor walking around on the walls. The “midriff plus big pants” look that pop stars would beat to death within a couple of years dates the video to 1999 just as much as all those pumps and L’eggs date R&B videos from 1990 to that year. The rap part involves Left Eye doing a cross between The Robot and a bunch of martial arts moves at an electronic eye, good for a laugh.

3)Monica, “Angel Of Mine”
SONG: Nearly holds the record for the single most generic song I’ve heard in any of these Billboard posts I’ve done, and that’s saying something (yes, it’s worse than the LeAnn Rimes song I had to listen to twice!) If I’m not entirely sure, it’s I’ve already forgotten some of these R&B songs…hell, just about all of them! The synth strings that show up in the second half of the song sound suspiciously like leftovers from around 1989 or so.
VIDEO: For about thirty seconds this video seems to be telling some crime story, then drops it. Weird.

4)Whitney Houston/Faith Evans/Kelly Price, “Heartbreak Hotel”
SONG: Generic R&B with an acoustic guitar. Obviously she could sing, but she’s not doing anything in this song that you couldn’t get from a lot of other people. What’s the gimmick with the title being borrowed from Elvis? How is that supposed to get attention? I don’t recall hearing this song in 1999 at all, but my memories may be faulty.
VIDEO: Her blonde-ish hair looks like an altered version of “The Rachel.” Or Annette Bening in American Beauty from the same year. Some of this is her on the beach and some of it’s her in a hotel. At least she didn’t look like a miserable emaciated drug addicted skeletor.

5)Britney Spears, “…Baby One More Time”
SONG: I’ve said it before and I’ll say it again: you could MAKE this song on your phone nowadays. I suppose to be fair I’d rather listen to this than Frank Zappa’s “The Adventures Of Greggary Peccary,” which is what I was listening to before starting this fucking post.
VIDEO: NO FUCKING COMMENT.

6)Sixpence None The Richer - “Kiss Me”
SONG: So the biggest hit of 1999 by a guitar-based rock band was a Christian song? Interesting considering that the biggest rock story of 1999 was fucking Woodstock ‘99, with all that rap metal and associated hate and Columbine accusations all over the place!!! Believe it or not, I don’t actually hate this–it’s probably the most listenable song on this list, since it borrows a few elements from dream-pop and shoegazer, and it doesn’t date badly to the era in any way.
VIDEO: The band sitting on a bench under the stars, only the female lead singer seems to be paying attention. She looks like the girl from that PS1 game Pandemonium (not its sequel, mind you.)

7)Christina Aguilera, “Genie In A Bottle”
SONG: I remember when this song came out like it was yesterday, because she was immediately tagged as a Britney Spears knockoff, but she really wasn’t–this song neither truly rips off Britney’s vocal style, nor the backing music, nor even the audience–the Britney song seemed aimed squarely at fourteen year old girls whereas, whatever else you can say about “Genie In A Bottle,” it didn’t seem as overtly teen-friendly. But what I don’t remember, curiously enough, is the song–I remember its name, and the person singing it, and the pop culture event of its release, but I wouldn’t have been able to hum it for you from memory at gunpoint, not before relistening to it for this post. And I probably won’t after relistening to it–it’s melodically and musically unremarkable through and through. At least the Britney song is hummable! If I stand a chance of remembering any of this song, it’s the dumb whispery bit she does at the end.
VIDEO: She writhes around on a beach and does some dance lines with some people, which means, you guessed it, the Midriff And Big Baggy Pants look comes out. Which is the part she really ripped off from Britney. Otherwise, her appearance could just as easily been marketed as “Sarah Michelle Gellar, but sexed up.”

8)Sugar Ray, “Every Morning”
SONG: God help me, but after all this teen pop and generic R&B I kind of liked this. It has a nice laid-back chord sequence and the vocal style is like a less obnoxious RHCP song. It has an obnoxiously yammering pounding four-four beat, I guess, but there’s worse sonic flourishes you could ask for in 1999. And hey, the chorus is good. A pleasant surprise, considering I haven’t thought about these guys or this song in years, except for that one album cover they did that had the naked chick from Baywatch on the cover.
VIDEO: People funning it up in what looks like a small-town dance hall. Cute enough I s’pose.

9)Deborah Cox, “Nobody’s Supposed To Be Here”
SONG: Big bleary R&B ballad with a humongousoid chorus. I guess the humongousoid chorus makes it stand out a bit. I’m getting very very bored with this genre despite only relistening to any of these songs once, and I can’t remember if I remember this song from 1999 or not, because only the big humongousoid chorus makes it stand out from about thirty other songs from these posts in any way shape or form.
VIDEO: Seems to be set on a Southern farm somewhere, which is a decent change of pace.

10)Ricky Martin, “Livin’ La Vida Loca”
SONG: Two components of this song’s arrangement save it a bit; one is the James Bond-ish guitar riff that only shows up once early in the song, and the other is that the “she’ll make you take your clothes off and go dancing in the rain” bit leading up to the chorus sounds suspiciously ripped off from a similar bit in the Chip & Dale Rescue Rangers theme song. I will state that I don’t think this song is as kitschy or bad as “Believe” or “I Don’t Wanna Miss A Thing” or what have you–I wasn’t looking over my shoulder with embarrassment while watching the video–but I probably wouldn’t listen to it of my own volition either since it’s still heard in public now and then. I would prefer it to the Santana/Rob Thomas song released that same year, though Ricky landing on the cover of TIME (remember that?) was probably a bit much. The whole “pop culture phenomenon being made fun of to death the week it happens” thing I talked about with “Believe” and other 90s hits probably applies to this song too but not as much as that other stuff; of course, Ricky didn’t last much longer, and his legacy had to be kept alive by stuff like William Hung and announcing that he was gay to get attention.
VIDEO: People bouncing around in a club and a car hits a fire hydrant. Crazy times bro.

OTHER SONGS ON THE LIST:
“I Want It That Way” (#15), “Smooth” (#19), “All Star” (#17), “Wild Wild West” (yikes), “Fly Away” by Lenny Kravitz, etc.- Grateful to not have to relisten to these, though I confess that I really liked “All Star” in high school. REALLY liked it.
Two of the highest ranking rock songs in the top 25 are Goo Goo Dolls’ “Slide” (which I don’t remember) and Pearl Jam’s “Last Kiss” (which I do) but those songs are like early 90s requiems by this point.