WHEN: Late '90s–mid 2000s
COMPLEX SAYS: Back in the day, the Limp Bizkit frontman who claimed to smash Britney Spears and beefed with Em, could always been seen rocking a red Yankees fitted. During the band's heyday, when albums like Significant Other and Chocolate Starfish and Hot Dog Flavored Water (most pause-worthy album names coming soon) were going multi-platinum, legions of fans could be seen donning the cap. By the look of things now, the 40-year-old Durst may want to start sporting fitteds again. #justsayin'