A secret year is chosen. Each round plays up to five songs from it: the Billboard Hot 100 top three, plus that year's Grammy Song and Record of the Year. Guess the year, rank the three Hot 100 songs, and pick which won each award.
The year you guess is the Billboard chart year. The Grammy ceremony happens the following year but honors that same period, so its winners belong to the year you're guessing. Song of the Year rewards the songwriting; Record of the Year rewards the specific recording (artist and producers), so the two awards can go to different songs.
Each round embeds the songs from Spotify. If you're signed in to Spotify Premium in this browser, the players play in full; otherwise you'll hear a 30-second preview. If a player doesn't load for someone — no Premium, region limits, or a track that's gone — open "If a song won't play" to get tap-to-open links for that round's songs in your own Spotify app.