[2] Ragsdale was born January 19, 1961,[3] in El Dorado, Arkansas, and attended Hendrix College, where he appeared in plays alongside Natalie Canerday.

He garnered attention as the young hero of Fright Night and Fright Night Part 2 and onstage in Neil Simon's plays Brighton Beach Memoirs and Biloxi Blues,[4] two of the three parts of Simon's trilogy, which ends with Broadway Bound.

He was cast in the pilot for Charmed, but refused the series to feature in the short-lived situation comedy Brother's Keeper.

[8] In 2017, he appeared in the role of Reverend Todd in the Off-Broadway production of Man from Nebraska at the Second Stage Theatre.

[9] In 2023, Ragsdale appeared as a vampire-hunting priest in the horror comedy Renfield, a nod to his Fright Night role.