Head Game: A Look At The Twenty Greatest Hats In Hip Hop History


…see what I did there?

Like a lot of things in the rap community, hats (yes, hats) don’t get nearly the amount of credit that they deserve. Really, though. People (mainly rappers) make songs about girls, guns, condoms, their collective enemies, etc., but rarely does Hip Hop take the time to celebrate the little things that make ours such a great culture.

One of those “little things” is the hat. More specifically, our collective ability to make the hat an essential part of any type of outfit, Hiphopically speaking. Think about it. The hat – even moreso than the DJ or the blunt roller – is the proverbial MC’s theoretical best friend. That’s a scientific fact. As far back as you can remember, your favorite rap cat rocked something on his head when he performed, & whatever piece of historic memorabilia or sports paraphenelia he had on, you had to have, too. At the very least, you convinced your pops to buy you a cheap knock-off, but that’s not the point. For whatever reason, since the beginning of time itself, it’s been one man, one mic, & most likely, his hat.

Today, we’re here to recognize the tremendous role that the hat plays in our glorious rap community.

Hats (or caps, depending on the style) are more than just the tilted finishing touches atop our haberdashery stash. Hats camoflauge bad hairlines, cover up wack haircuts, & even hide the scars, keloids, birthmarks, bald spots, or tattoos that our hair won’t. I’ve known some dudes that even put drugs & weapons in their hats in my day, & if they weren’t doing hard time in prison right now, they’d definitely co-sign this post in the comment section.

Aside from the weather itself, I’d venture to say that the Hip Hop target demographic has helped bolster hat sales across various markets. Seriously, how many urbanites rocked snow beanies with earflaps before some raptastic Hiphopper spat youtubilicious rhymes whilst wearing his? As ridiculous as a hat may seem to the outside world – much like jello & White women – there’s always room for a hat in Raptopia.

Name a rapper & I bet you there’s some head gear you can associate him with. Even the lesser MC, who didn’t garner the same amount of your attention & respect has some sort of idiosyncratic derby, because that’s just part of being a rapper.

Like everything else, times change, & perhaps one day the hat will become as useless as a CD player (on the contrary, hats better step their climate change game up), but for now let us tip our hats (no pun intended, for real) to the 20 greatest hats in Hip Hop.

(In no particular order…)

The Kufi

The Trucker Hat

The Viking Helmet
*Or any helmet that has no place on top of a person’s head in an unprofessional manner

The Top Hat

The Beanie

The ‘Coon Skin Hat

The Winter Hat

The Old Man Cap

The Durag

The Hood
*This wasn’t a hat, but thanks to the rap music video, it’s close enough

The Fisherman Hat

The Kango(l)

The Visor

The Fitted

The Snapback

The Stocking Cap

The Bucket Hat

The Wave Cap

The ‘Rag
*See “The Hood”

The Ski Mask

…& as somewhat of a bonus, #neverforget…

The Jimmy Hat


5 comments on “Head Game: A Look At The Twenty Greatest Hats In Hip Hop History

  1. markdub7 says:

    Would LL really have been Ladies’ Love if he didn’t have something covering his missile shaped dome for so long?


    • Tony Grands says:

      I’m convinced all his hair is gray, like some sort of generational albinoism, & the reason he wore the big hat in the early years is because he was still learning how to deal with the affliction…


  2. […] Head Game: A Look At The 20 Greatest Hats In Hip-Hop History [The Tony Grands] […]


  3. I really enjoyed reading this blog post, keep on writing such interesting posts.


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