If you want to find some jams that were popular in Canada in the 1950s to kick off your weekend - or just want a random assortment of trending songs by era and location - the website Radiooooo is a great interactive trip.
Screenshot: David Murphy (Radiooooo)
Its premise is simple, but effective: You pick a decade from a timeline that spans the full 20th and 21st centuries (1900 to the present day). You then pick a country from a giant, old-timey map of the world. Assuming there's music in Radiooooo's database for that country and time period, you'll hear songs that were popular for that combination of location and decade. It's as easy as that.
What else would you listen to in the 1990s? Screenshot: David Murphy
There are some combinations that aren't going to pull up any music whatsoever - sorry for those looking for popular hits from Turkmenistan in the 1920s. However, if you happen to have a large depth of musical knowledge about a particular location and decade, you can contribute songs that you think Radiooooo should add to its mix.
Don't just try to upload every song you love in music library to the site, however. As The New Yorker described in a 2016 profile of Radiooooo:
Radiooooo employs curators who spend hours every day combing through hundreds of submissions from almost thirty thousand contributors, from all over the world (Troubat refers to them as "treasure hunters"). The curators make sure the audio files are high quality, and judge whether or not the song fits the Radiooooo aesthetic, which can be difficult to define.
If you find a song you like while playing radio Carmen Sandiego, you can assign it the stereotypical "heart" to track it in your profile, should you sign up for an account. Depending on the availability what's playing, you can even click on a little coin icon to buy the track directly from iTunes.
My favourite part of Radiooooo is its taxi feature, because it lets you create a playlist of parameters by choosing only the decades and locations you care about. From there, Radiooooo will create random combinations of songs to send your way. I only wish the site had a way to skip past music you don't find very interesting - either I'm blind and have missed it, or I've spent too much time taking in the sun on the site's "8-Bits Island". Bon voyage.
All Right, Vatican. Let's hear what you got. Screenshot: David Murphy