I know there are at least five...those songs that always cheer you up when you hear them, or evoke fond memories....
What five songs are timeless to you, yet, to others, are clearly dated? And I mean seriously timeless—and seriously dated. For example: If they were to play them on a mainstream radio station, these are the songs that would pleasantly surprise you and possibly make your day, yet they wouldn't feel out of place. But there is a rational side of you that knows that if your friends or family heard the same songs come on, they'd titter, make fun of it, and/or change the station before the first glorious chorus hit. Chacun à son goût.
Bonus points for posting equally dated videos.
Here's my list. Much of my list falls somewhere in the '80s, if not in the early '90s:
Information Society "What's On Your Mind (Pure Energy)"
Men Without Hats "Safety Dance"
Roxette "She's Got the Look"
INXS "Need You Tonight"
2 Unlimited "No Limit"