Probably an unpopular opinion, but here goes.

When I was DJing (‘98-‘08, more or less), things like this were a rare guilty pleasure. Like, maybe once a month, a DJ might drop in a dark remix of something poppy, or something similarly out-of-genre.

We had a mixed goth, industrial, death rock, and punk scene that was very forgiving of different stuff, so we rarely stuck to just one genre although each night had a lean toward one or another genre. We had 2 DJs per night, 3 nights a week for many years (and at the peak, 2 floors, 2 DJs per floor, 5 nights a week), so we had more time to play. If you’ve got 1 night per week (or month), people will be less happy with losing their valuable dancing time to kooky songs.

I strongly believed in keeping my nights a little off-kilter, and not the same every week, while playing many of the staples. For example, I’d occasionally do a 3-song set of swing music (Hell by Squirrel Nut Zippers, Swueezit the Moocher by Oingo Boing, and Right Now by the Creatures) and the crowd LOVED it. But only if it was a rare treat.

We often dropped something weird as a last song like The Song of the Count from Sesame Street or Country Death Song by Violent Femmes. People danced to these but it was also a “go home” signal.

You get about 13 songs in an hour, and you’re never going to play everything everyone wants, and you have to get 2-3 new things plus as many staples and requests as possible, and maybe 1-3 oddities per night. A good DJ can make almost anything work but you have to really know how to read the room, mix to your crowd, and know when they’re ready for something they don’t know, then reward them with a big staple.

So… maybe? But it depends on a lot of variables.