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Lester began his acting career as a teenager; one of his early parts was the recurring role of Roy on The Facts of Life. His early voice acting parts include roles on G.I. Joe and Jordan Knight on the New Kids on the Block cartoon.
From 1992 to 1998, Lester performed the voice of Dick Grayson in Batman: The Animated Series, and the sequel series The New Batman Adventures.
Lester's recent parts include roles on General Hospital, Gilmore Girls, The Bold & the Beautiful, 7th Heaven and Zoey 101.