Back in high school I was listening to rap metal and punk music I remember the first time I ever had an idea about New Era 59/50's. The first artist who introduced me to fitteds was the singer of Limp Bizkit which is Fred Drust. (pictured below)
He would always wear a red New York Yankees fitted cap, every time you'd see him.
Every time I saw the music video for "Nookie" I would watch it and imagine myself wearing that fitted cap and how it would look cool.