Yes! Michael Stipe.

That was fast.

Here's one more, then I have to go..
Attachment 39068

I had to resort to TinEye. That's a good one.



Hint: The mouth/teeth/chin are a dead giveaway now that I know who it is.

Bruce Willis?

Yes!

Shennanigans

This one is super easy, but I just post it for giggles. Still, let's hear your guesses.
Attachment 39077

What with the jacket, the hair and the earring, I'm glad he ain't one of my friends.

It's like a gay, glitzy, pirate.

that one is too easy

Omg - did we really look like that in the '80s???

Aaaaaaaaaaaaaaa!!!

I think Schwimmer sort of told people that he was a douchebag back in the day.

no shenaningans

How's this one? Too easy?
Attachment 39082

What do you mean 'we'? 'We' never looked like that.

:D

Steven Tyler?

Yes! Steve Tyler. You're good at this.

So here's one. I think this is harder. The funny thing is, I knew a guy in high school who looked just like this.
Attachment 39084

Well, it was Steven Tyler, or the Joker.