So… at the rate I’m going, I probably won’t reach my mini-goal to catch up with the entries on this challenge by the halfway point. I’m in no rush, though – I’ve got eight whole months to play catch-up! And now that I’m nearly 100 entries deep into the challenge, it’s safe to say that this is the single gayest entry thus far. If you have some semblance of experience in and knowledge of contemporary pop culture, you probably have some idea of who RuPaul is. Nowadays, he is best known for hosting the Emmy award-winning reality show RuPaul’s Drag Race (which I still haven’t seen, so stop asking me ok?), but his fame was initially spearheaded by his role as an actor and personality icon throughout the 90s. In particular, he was especially prominent in causes for the advancement of the LGBT community – which continues to this very day – as hinted by his consistently gender-bending appearance and major role in the drag community.

In the gay community, RuPaul is as ubiquitous as Elvis Presley or Marilyn Monroe. Personally, though, I’m not a huge fan. I do appreciate his very image as one of the few openly gay men to be as prominent as he was during a time when such representation was few and far between. In some ways, this representation is still very invisible, so the mere fact of his success is a success for LGBT folks as a whole. Nonetheless, the drag community is historically replete with sexism and especially transmisogyny, and RuPaul’s upholding of these values throughout his career certainly hurts this particular cause. As I mentioned, I still haven’t watched Drag Race, and I won’t lie – part of that is due to the claims I’ve read by trans folks taking offense to casual usage of the t-slur and the s-slur. These values don’t exist in a vacuum, and I’m not so sure if RuPaul is doing much with his pedestal of visibility to openly shine a light on these problematic aspects of a certainly well-intentioned community.

But in any case, I’ll try to set aside these biases to judge this single, like any other, on its own merits. The single of the day is RuPaul’s “Supermodel (You Better Work)”, the breakthrough hit that jumpstarted the performer’s career. While it only made it to #45 in the Hot 100, it quickly found a following with gay audiences and made it up to #2 in the dance charts. Mainstream listeners could probably note its similarities with Madonna’s smash hit “Vogue”, released two years earlier. Indeed, it has a similar deep house groove, complete with driving piano and string sections guided along a danceable, bass-heavy rhythm (although “Supermodel” is certainly more uptempo). Additionally, both songs pay particular homage to the gay ballroom scene arising from Harlem in the late 1980s. The act of voguing was lifted directly from this scene, while RuPaul’s song references a large amount of slang typical of the scene (e.g. “sashay”, “shantay”, “you better work”, etc.). Finally, while “Vogue” contains a bridge wherein Madonna orates names of flashy golden Hollywood figures, RuPaul reads off a name of hypothetical women that could possibly be working their way along the runway as he speaks.

Since its release and success, “Supermodel” has been noted as one of the ubiquitous anthems of not just the gay community, but the modeling community as well. I’ve listened to a few other RuPaul songs, and it seems that he has built an entire career off of crafting plainly forgettable dance songs fit for strutting along to on an catwalk. With that said, “Supermodel” is probably the best of the bunch. It’s brimming with personality and fervent energy, and while the achingly 90s house production hasn’t aged well, it at least stays firmly on the charming side of age. RuPaul acts as ringmaster to the whole affair, and he has never sounded as convincingly as he does here. Unfortunately, does it fall into the dance music trap of folding upon itself after the first chorus; frankly, if you’ve heard the first minute of this song, you don’t really need to listen to the next three.

Still, this song really could have been a whole lot worse. I’m so used to enduring all breeds of trashy, campy humor from fellow members of the queer community, it’s a tad surprising to encounter something so wholesome in its extravagance and gay display. It’s a shameless love letter to one’s entire queer identity in the form of a bouncing dance track, and though it’s repetitive I can’t really say it wears out its welcome. Nevertheless, the mere thought of this being performed by a drag queen inevitably unleashes the misogynistic implications of “performing” gender – as well as all the transphobia – so I can’t quite enjoy this one completely. But once again, it could have very well been so much worse.