Why Jem? We have all three seasons on DVD and my daughter has been consistently obsessed with it. So, I've seen every episode at least once - and some 5 or more times - and heard every song. Also, as hilariously unnecessary as it may be, Victoria and I have actually argued about which Jem songs are the best/worst/creepiest. Because that's something worth (gently) arguing about, right? Right.
Why five? I dunno, it just feels like a good, and manageable, number. I've also arbitrarily decided that I'll include at least one video from each of the three groups in the series: The Holograms, The Misfits, and The Stingers. I'm not sure that any of The Misfits' songs actually deserve to be in a 'best of' list, but it feels somehow wrong to exclude them.
One last note on the actual songs that I chose before I actually get to posting them. If you watch these and think 'hey, that's not bad', don't start thinking that the other 150+ songs aren't bad. Because they mostly are. On the whole, the music is, at best, awfully cheesy and repetitive. The songs that I'm including here are notable precisely because they're exceptional in some way - they're unlike a typical song from the series. So, it's actually a very misleading list. Anyway...
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The Misfits - "Lovesick" (3x02)
Like I said, The Misfits aren't given much to work with. Most of their songs are generic mid-tempo rockers with fairly monotone melodies and uninspired lyrics about being infantile bad girls. The only thing interesting about them is Pizzazz's vocal delivery, which features a pretty delightful snarl. But that gets old quickly when she employs it on pretty much every song.
Anyway, I'm a bit ambivalent about including "Lovesick". On the one hand, the vocals and the lyrics are a huge departure from the usual. It's also got some really slick production and an atypically fancy video. But that novelty comes at the expense of Pizzazz's character, who is never worse than when she's shown fawning over Riot. Ugh. I might've just as easily gone with "I Like Your Style", I guess.
Jem and the Holograms - "I've Got My Eye on You" (1x03 & 2x01)
Jem songs are often bathed in romantic clichés, but rarely are they actually hot. This is one of the rare exceptions, which means that it's worthy of inclusion here. (It's relative, of course. "Hot" on a kids' cartoon can only be so hot.)
This is, by the way, the second version of this song, from the second season of the show. It also appear early in the first season, where the video made the song a bit unsettling, if not creepy. In that version, Jem sings the song to a visibly discomforted Rio, who is developing a crush on her. Which would actually be okay, because Jem is the alter-ego of his girlfriend, Jerrica. Except that she hasn't told him that. (And she never does!) So, in the video Jem is hitting on a guy who is dating someone else... though that someone else also happens to be her. Weird and unnecessary.
The Stingers - "Take It or Leave It" (3x02 & 3x11)
Every group has some duds, but The Stingers have a higher proportion of good songs to bad than either of the other two groups. The Stingers were also around for only the final, half-length season and had something like 10 songs, so that might have something to do with it. They also had the only male vocalist, so that novelty could also explain why so many of the songs aren't terrible. Maybe.
Anyway, this is the second Stingers song we hear, but it effectively serves as their introduction - they're unrepentant assholes who treat everyone like garbage and they like it that way. This song is a bit of an exception to the rule that these songs are, themselves, exceptions: it's entirely indicative of The Stingers' sound and content, and it just happens to be the best of their 'we're better than everyone' songs.
Jem and the Holograms - "It Depends on the Mood I'm In" (1x12 & 3x09)
For whatever reason, the songs about fashion are usually better than average - the next song on this list is also about fashion.
The Holograms' songs are usually overly serious - emo music for pre-punk, pop-listening tweens, basically. But when they decide to just have fun with a song, it usually turns out okay. Or, as with this song, better than okay. "It Depends on the Mood I'm In" also benefits from being somewhat meta, and being a bit playful with the whole hologram/dual-personality conceit that, when it's addressed, is usually discussed in a really tedious manner. And it includes the trademark "truly outrageous" line, which appears in a couple other songs, too. (And is a strange slogan for a group that is neither "true" in the sense that Jem is holographic, nor "outrageous" in the sense that they're really boring. Discuss.)
The Stingers "All in the Style" (3x09)
Like I said before, The Stingers are kind of bad ass. Well, bad ass for an 80s Saturday morning cartoon, anyway. They're telling you to "catch them [people] unaware" and "make them stop and stare". And they want you to "set the world aglow" and "radiate heat". I might have said that "I've Got My Eye on You" was hot, but this song is saying that you are hot.
It doesn't matter that, within the plot of the episode, Riot is being disingenuous - he's complimenting a designer because he wants to convince her to work for him instead of Jem. This is a genuinely smart and even empowering song, if also a somewhat cynical one about how your power is connected to your ability to capture people's attention. Still, a Jem version of this song would be full of empty platitudes while this Stingers version, at least, addresses your agency.