Does anyone have any thoughts or suggestions on how to create a playlist of songs from my library that have been released as "singles" or "Top 40s" across a time period?

Let's say I wanted to throw a 90s party, and I wanted to create a playlist from my library using only songs that people are likely to know. I recognize that's totally subjective, so maybe that's why I'm struggling to find what I want. I can create a playlist based on album release date, which gets me a bit of the way there, but the playlist is going to include a lot of "deep cut" tracks and whole albums that few people know. I'd rather not spend too long curating the list. I was hoping for a way to just find popular tracks, and it seems like basing it on "chart toppers" would be a good place to start. Ideally, it would be genre-independent, but limited to songs that got decent radio play, so Backstreet Boys to Korn to Shania Twain are fine. Yo Yo Ma maybe not so much.

It doesn't seem like Plex has information available in the filters to achieve that. It does have "Popularity" as an additional column header if I list my music by "Tracks", so I guess I could sort by that and limit the results to some value. It feels a little clunky, though, and I'm not sure where it's getting that information.

I know that Library Radio is a thing, but I can't seem to make it do what I want. I only have 4 stations on the web interface: "Library Radio", "Deep Cuts Radio", "Time Travel Radio", and "Random Album Radio". Clicking on them just starts playing music from a wide selection that I have no control over. I know that "Decade Radio" exists, but it doesn't seem to be giving me what I want, either. It frequently pulls instrumental tracks from movie soundtracks. I have "Smart Shuffle" enabled on my server. I'm not sure if that's helping or hurting my experience (I've seen some very mixed reviews on that feature). I also can't find "Decade Radio" on the web interface; it seems like Decade Radio is only available on Plexamp.

I'd rather just create a playlist. That way it would be available everywhere, and I could tailor it a little bit, if needed.

So, yeah... any tips? It seems like the "filter by decade, sort by popularity, and limit by count" might be my best option right now.