在七年级的时候出演了他的第一部戏剧，当时他住在北卡罗莱纳州。在那之后没多久，他搬去了俄亥俄州罗（Rossford），并就读於（Rossford High School）。Jonathan于1999年从Otterbein 学院毕业，之后他继续深造奥特本大学，他主修的是Theatre Program。在他离开之后，他搬去了纽约并继续演戏。Jonathan的荧屏处女作是《Season of Youth》，他并以该片赢得2003年棕榈滩国际影展最佳男主角奖。
After graduating from Bolles High School in Jacksonville, Florida, Ashby took a degree in psychology and business administration at Fort Lewis College in Durango in the state of Colorado, and then moved to New York where he took drama classes in the Neighborhood Playhouse. Early in his career he took part in the soap opera Loving, and an episode of MacGyver, also got a small role in the 1990 movie Mr. & Mrs. Bridge with Paul Newman and again in 1990 he starred in the independent film The queen of hell alongside Karen Black.
