At what point in your life do you take a step back, look in the mirror, and say to yourself, "You know what? Let me take this off. I'm getting too old for this look?"

When you start to ponder if you look silly...


...or totally ridiculous?

By the way, Pissy, Zorro called: He'd like his mask and his swagger back. And baby hair only works for babies.

I'm not saying once you reach a certain age you should start wearing suits everyday and become boring, dull, and lifeless. But, when you're inching closer and closer to 40, do you want to dress like you're ready to tell someone "Now watch me...yuuuuuule" at any second?

Is 30 the new 20 because we're living longer or is it because people want to lead 20 something lives longer than time allots?

There's always been the stereotype that women hate aging, but more and more it seems as if men have as much problem with getting older as their female counterparts.

Take LL, who often looks like a walking advertisement for botox.

Then there's J.D., who mostly likely cut his braids only because of his receding hairline.

As I get older, I wonder how my behavior will change. When I'm 30, I don't see anything wrong with being in the club.

At the same time, I don't want to end being the old man at the club. If Jay and Jermaine weren't rich, don't you think people would be asking why are Sanford and Son still dressing like the kids? And after a while, you go from that to this:

I don't want to end up 87 still getting giddy about being in VIP. If you're old enough to remember black and white televisions, stay home. Pop-Pop and Grady look like old school players, don't they? I wouldn't be surprised if they have eight prescription bottles stashed in the pockets of their suit jackets, though.

So many older artists are doing a complete backtrack in an effort to appeal to consumers who just left prom.

Isn't R.Kelly too old and too creepy to still be looking for new McDonalds play-land friends to play "sprinkle, sprinkle" with?

And after a certain age, does it ever get old to glorify drugs and materialism?

Here's to hoping I can age gracefully and get to the point where I'm content with my age, leaving the matter of proving anything to those still trying to find their own way ---like wack tats on the right and the Lost Boys pictured above.

I realize you're only as old as you feel --- but some of these people look and sound the fool. Feel me?