In the early 2000s, the trucker hat became a mainstream fashion trend, predominantly among suburban American youth. This came about with a sense of irony due to the hat’s rural or blue collar association and typically older demographic. It has frequently been donned by celebrities; musician Pharrell Williams and actor Ashton Kutcher in particular helped make the hat fashionable. However, in a 2008 interview with Fashion Rocks magazine, singer Justin Timberlake claimed that, while Kutcher has been cited for popularizing the trucker hat, Timberlake had been wearing them since the age of seventeen. The trucker hat trend was lampooned in the King of the Hill episode “Grand Theft Arlen”, in which teenagers confuse Hank Hill by asking where he bought his Strickland Propane cap and questioning its irony.
Comedian Judah Friedlander is known for his signature trucker hats, which depict various humorous phrases. Having worn trucker hats since the 1980s, Friedlander claims a fondness for them and has ignored any rejecting or embracing fashion trends surrounding the hats throughout the decades. In a 2007 interview, he stated:
“I was never into anything trendy. If I’m ever doing something that happens to be trendy, it’s probably a coincidence and I don’t even realize it’s trendy. Just a note: I’ve been making and wearing trucker hats for years–since the ’80s actually, when those were pretty much the only kind of hats you could get. I remember about 10 years ago, people used to make fun of me for wearing trucker style hats. And then when they became trendy a couple years ago, those same people came up to me and said shyly, ‘Uhm, where do you get your hats? I need to get some.’ Years ago, some people used to get angry with me for wearing them and someone even called me racist for wearing a trucker hat ’cause I looked like a redneck. I bet now, some people think I’m a loser for wearing them because now they’re out of fashion. But you know what, I never wore ’em to be ‘in’ or trendy or cool. I just like ’em. And I’ll be wearing them long after they’re a not a trend.”