Grandson of Robert Thomas, one of the founders of the South Australian newspaper The Register, Skipper was educated at the Adelaide Educational Institution. He joined the literary staff of The Register, then became the shipping reporter for Adelaide newspapers and journals. He was an art and drama critic, a satirist and caricaturist. He contributed to the 'Echo' column in The Register, and also to Knightsbridge Papers and the Observer Miscellany. Under the pseudonym Hugh Kalyptus he edited two issues of Yellow Flag and Torrens Island Terror, a journal published at the quarantine station on Torrens Island.
