John Ventimiglia from the Sopranos. I stumbled across this last night and was surprised to see his birthdate listed as July 17, 1968 because I thought he looked much older than that. Several sites confirm that date, though several others show him as being born in 1963. I'm not sure which is correct, but either way, I think this guy would look a lot younger without the fringe:
Good find Razor, no doubt he would greatly improve his look by being sly
Ventimiglia?
I thought that was a vaginal disease.
Ventimiglia?
I thought that was a vaginal disease.
hell, you probably got treated for it in the 80's anyway, huh robbie?
Ventimiglia?
I thought that was a vaginal disease.
hell, you probably got treated for it in the 80's anyway, huh robbie? 
Don't recollect ever havin' a vagina back then....but, hey, I did drink W-A-Y too much.
Don't recollect ever havin' a vagina back then....but, hey, I did drink W-A-Y too much.
I do recall you having the kind of hair that if someone saw you from the back they might think you had a vagina.
Don't recollect ever havin' a vagina back then....but, hey, I did drink W-A-Y too much.
I do recall you having the kind of hair that if someone saw you from the back they might think you had a vagina.

I think he had that taken right before the operation ....
Former actor, turned republican presidential candidate Fred Thompson is another "needs to go sly" guy.
BTW, that's his wife, not his daughter!!
Trent Dilfer. I saw him doing commentary on the NFL network last night. He'd look like a total badass if he'd lose the horseshoe and go sly. Not sure when this picture was taken, but he didn't have any hair on top last night.
Perhaps Brian Billick wouldn't be out of a job if the Ravens would have kept Dilfer, horseshoe or not.
Former actor, turned republican presidential candidate Fred Thompson is another "needs to go sly" guy.
BTW, that's his wife, not his daughter!!

Sly might not look as good on Fred as you might think. His face is pretty weather-beaten. If he shaved off his hair, the skin underneath would be in much better condition than the skin that's been exposed to the elements and the contrast between the two would look strange. I've seen other people like that who shaved and really did not look all that great.
Yes, he used to be completely shaved. I can't imagine why he thinks MPB looks better. 
Yup...complete shame when one of the best "sly-pioneers" goes to a scruffy horseshoe look...
REAL lame...that cat was totally one of my early inspirations to shave my head smooth...?!?!
I think it's a "everyone's shaving their heads thing now... let's do the opposite even if it looks horrible...let's go natural!
Uh, yea right, great new look bro...not!