I've noticed this as well.  I don't know his name, but there is a rapper who wore a Pirate hat in one of his videos, and had his kids, also in the video, wear Pirates hats too.  My friend showed me the video on his phone, but I forget his name.

Also, while I was watching "Best Damn" from the Super Bowl last year, P. Diddy had a Pirate cap on.  Why?  I couldnt tell you.

Here in Pittsburgh, I'm also noticing that there are varying styles of Pirate caps.  Theres one with a "P" inside the shape of Pennsylvania with a star where Pittsburgh should be.  I've also seen several other adaptations of the "P" all in flat billed, hip-hop style.

My only explaination for this is that, from a hip hop perspective, perhaps the "P" looks pretty badass when compared to other team symbols in the city.  Think about it.  If your trying to build up your "street cred" by wearing stuff that shows yer from "Up in da P-G-H" do you want to wear that steeler symbol?  No, thats a little to yinzr.  Do you want to wear a silly looking skating Penguin?  No, hockey isnt a hip hop sport, whether the Pens have Geroges Laraque or not.  That leaves you with the Pirates solid black hat, with a "P" that looks pretty sweet on the hat.

Overall, if you think about it, the Pirate's hats are pretty badass when you remove the futility it represents. While I find it slightly disturbing, I can see where they're coming from.

Just in case, I'd leave my Bucco cap at home when I'm going into Wilkinsburg, or look as nerdy as possible while wearing it if I must wear it there.

This is kind of old school, but Chuck D from Public Enemy used to wear Pirate hats all the time. A couple of quick examples: One, Two, Three, Four.

He's claimed that it's because he liked Roberto Clemente, though I bet the "P" logo was also a consideration (for obvious reasons).

If you like rap, "Fear of a Black Planet" and "It Takes a Nation of Millions to Hold Us Back" are worth a listen.

http://blogs.indiewire.com/morganspurlock/archives/Snoop.jpg

I think i also remember Ice Cube wearing a Bucco hat a long while ago.

From what my friend told me, the whole flat bill thing has to do with fresh and clean and brand new.  Basically letting people know you can afford a whole heap of brand new hats.

Also, the most important thing to do is match your hat with your sneakers.  If you wear a Yankee flat bill your life is simple, but doesn't lend well to having any color on your kicks.  Whenever you see a fella or lady with a flat bill on immediately look at their shoes to check if they match...

Chad Cordero. He's kind of an outlier, though.

That is why it is embraced by the hip hop community. As a 17 year Pirates/Hip Hop fan I can tell you that I have seen Snoop Dogg wear Pirates and Steelers gear everywhere, Chris Brown wore a Pirates hat in his "Wall to Wall" music video, and Ice Cube has worn Pirates hats on a couple occasion including in his movie "Are We There Yet".

The Phillies have the most popular hats in Hip Hop, followed by the Yankees, then the Pirates are probably a somewhat distant third. I think these teams hats are popular, becuase they look somewhat badass and retro.

Your Welcome Everyone

I've noticed this too.  I think a lot of people are more simple than you're giving them credit for, most people I ask why they're wearing a bo sox hat or a pirate hat simply say they like how it looks, the color scheme, etc.  And also the yellow P on black is simple, but looks "fresh."  What's also funny is that most Pirate fans are doubtfully the demographic that wears the flat billed pirates hat, most Pirates fans are usually suburban Pittsburgh kids who love baseball or jewish kids from Squirrel Hill, I'm not being steriotypical, it's just I notice that a lot of jewish people with Pittsburgh roots are buccos fans.  Anyhow, it's a good thing for the Pirates, we have few things to be proud of, at least our hats are fashionable.

The OBVIOUS influence for the popularity of the flatbill Pirates 59/50 hat is this guys:

Perhaps the "BP" stands for "Big Pimpin'"

I've seen a surge of Pirate hats in Oregon. Unfortuately, they're wearing the alternate cap with the red bill.

In New Jersey, and especially around Newark, a good number thuggish looking people wear Pirate hats. New Jersey is Yankee and Met country, so I knew something was off. It turns out that black and gold are the colors of a street gang called the Latin Kings. Since I go to law school in Newark, I am less amenable to wearing my Pirates hat now that I have this information.

...Dr. Dre

http://bp1.blogger.com/_Pqpmm2T6j4g/Rkanza4kGWI/AAAAAAAAAco/vXi_ZQ1GVwA/s1600-h/dre.bmp

I just saw two more today (in Kansas)! Another traditional black and an all gold with a black 'P'. Am I living in some kind of Latin Kings outpost?