Find a year for music you know you may like, and then add each month of the year to a playlist. This will give you time to enjoy a range of the time period's biggest hits, before you move to the following month per calender year. Doing it a month at a time means you can learn a decent amount of tracks by pretending they just "came out".
The year is 1979. Just in. The Police. LMAO. Basically, just act like it's all alien to you. Or if you want, just play the songs on Wikipedia lists that you don't know, just to see what you think of them.
Personally, I like to skip really cheesy stuff, as in novelty songs. So a month filled with nonsense like Black Lace or something just as silly, does nothing for me. It's all embarrassing as well.
It's a great way in general to get through a whole year's worth of popular music without any pressure.