From the relatively easy, to the damn near impossible...

Remember, no cheating.

Who is this?

Attachment 45413

If somebody gets this, I'm just gonna assume they cheated.

Or they've seen the pic before.

Brooke Shields?

It's a girl, I can say that for sure.

It's someone who is likely 45-50 today. Wasn't famous when younger, because they aren't recognizable here. which means probably isn't an actress because actresses generally achieve fame while young. So who else achieves fame? Politicians? Is it Sarah Palin? I've seen pictures of her as a young mayor, and she didn't look like this. But that's all I've got for now.

When I first saw this pic, I said the same thing. I thought it might be Charlize Theron.

It's not a female.

Hints: Male, singer, not currently with the group he's most associated with

ETA: Actually, after some research, the band he's most associated with may currently be an on again, off again situation.

Well "on again, off again" rules out Paul McCartney. Maybe Sting? Or Ozzy Osborne. It's got to be someone pretty big, to have had a group he's known for AND still be famous outside that group.

Eddie Van Halen?

Is that the Smashing Pumpkins dude?

Billy Corgan?

edit: It really looks like a girl. But the cheeks look like Corgan's.

Gene Simmons?

Wellwellwell, Glatt wins. Again.

Man, I just knew this would be a stumper.

It's Billy Corgan of Smashing Pumpkins fame.

Good eye, Glatt!

Thanks! :) The eye had very little to do with it. It was the haircut, which gave me the age, (which happens to be my age, btw) and your clue that it was a musician made me think of musicians who are my age. There aren't that many.

Three that may be easy or difficult
 

Number 1

Number 2

Number 3

Number 3 is Jennifer Aniston.

Number 2 is familiar, but I can't place it.

Number 1, I got nothing.