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- By DJ Ill WillWatch The Twentys "Careless " Video, the latest video from The Twentys, which dropped on Wednesday, May 15th, 2013. The Twentys's horizons are broadening with each new release, and The Twentys "Careless " Video is no exception. It's a worthy addition to a catalogue that has seen much growth since The Twentys stepped foot in the rap game. We're looking forward to hearing more.