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NPR has a feature on Finding D.W., the show hosted by Jason Szwimer who once played the voice of the sister D.W. on the cartoon Arthur. The series tries to find answers to why the character was voiced by so many men.
Szwimer says that a casting director told him the voice was meant to be huskier because D.W. was supposed to be a rough and tumble girl which was why 8 different boys played D.W. who Szwimer talks to in the series along with other people who worked on the show.