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This Trope plus Rap times Spinal Tap equals Fear of a Black Hat. N***as With Hats are never without some kind of sick headgear.
Ray Stevens considered it as the ultimate route to fame in country music in 'You Gotta Have a Hat'; ultimately, he gave it up.
Devo's Energy Domes, originally modeled somewhat after ziggurats (not to be mistaken for flowerpots, lampshades, or pet dishes (Jerry Casale still offers a reward of 1000$ to anyone who can find a flowerpot in that shape that predates the Energy Dome)).
One-man band That One Guy, who gets bonus points for wearing a nice hat on top of another nice hat.
In the late 1980s through the mid-1990s, there was a swarm of so-called "hat acts" in Country Music, many of whom followed the example set by George Strait of wearing pressed shirts, jeans and cowboy hats. Some actually fit well into that image and did not seem to be following the leader (e.g. Garth Brooks, Alan Jackson, etc.), while others were blatantly derivative. Come the end of The Nineties, "hat act" was largely a derogatory term in the genre.
Lady Gaga seems determined to have as many improbable hats as possible. To the point where her entire head is sometimes hidden by her headgear when she looks down.
Dome, the (main) side project of Wire's Gilbert and Lewis, gained a small degree of notoriety for their outlandish stage costumes, particularly their enormoustubular hats. Also double as Cool Masks.