Madonna dated Vanilla Ice? I don’t remember that, but somehow, I’m not surprised. I was born in 1985, so a good chunk of the 90′s was spent playing soccer and dress-up, I wasn’t really keeping up with celebrity gossip. I didn’t care so much about that stuff until about 1996, when puberty kicked in.

I definitely remember all of the people, but had no idea that any of them dated. Some of them make total sense (Leo and Liv), and some don’t at all (Jack Black and Kathy Griffin? What?) But still, what a fun little window into the incestuous world of 90′s celebrities.

You can check out more awesome celebrity couples from the 90′s on Buzzfeed.

Do you have a favorite couple from the past?