Bilgore graduated with a degree in Theatre from Dartmouth College. His early theatre career included:

- Training at the National Theater Institute at the Eugene O'Neill Theater Center, where Group Theater founding member, Morris Carnovsky, flatteringly named him, "The Voice!"

- Being selected by Sir Ralph Richardson to perform in a summer season of the National Youth Theatre of Great Britain at the Shaw Theatre in London.

- Graduate training at Guildhall School of Music & Drama in London. Legendary Royal Shakespeare Company director Sir Trevor Nunn stated: "He is what I understand to be an actor; he is detailed, he is truthful, he is insightful, he is original, he is multiple."

After moving to Los Angeles, Bilgore won critical acclaim and a "Best Ensemble" Dramalogue Award for his performance as "J.J." opposite Patricia Heaton in her stage production of The Johnstown Vindicator. He then went on to star alongside: Bob Newhart in the CBS series, BOB; Steve Harvey in the ABC series Me & the Boys; Shelley Long and Robert Hayes in Kelly Kelly for the WB and guest starring roles on many top shows, including his portrayal of "Wayne", the delusional robot creator in the fan-favorite, Emmy winning, "Mac & C.H.E.E.S.E" storyline on Friends. Prolific TV and Oscar nominated (Quiz Show) producer, Michael Jacobs cast him in two of his shows and once announced Bilgore to be "the best deadpan in town!"

Jeff Nathanson (writer, Catch Me If You Can) created the role of "Kilgore" for Bilgore in his Fox pilot, The 900 Lives of Jackie Frye. Kathleen Turner proclaimed that Bilgore's portrayal of "Walt" was her favorite in her ABC pilot, Style & Substance. And Paul Simms (creator of News Radio, EP of Girls), alongside legendary comedy director, James Burrows, selected Bilgore to star as the bumbling science teacher, "Peterson", for their ABC pilot Dexter Prep.