Roy Raymond, Jr., the grandson of Roy Raymond, Sr., presented a tabloid television series in Gotham City called Roy Raymond: Manstalker. He was considered by many as arrogant, inept, and a huge embarrassment to his grandfather. Batman described Roy as one of the few detectives he admired, but that he "chose to waste his talents on daytime television".

Roy eventually moved to Keystone City, where he became a pundit at KN News. There, he was manipulated by the villain Spin to start a smear campaign against the hero of Keystone City, the Flash. In Superman #669, a flashback shows that Roy Raymond did indeed have a show under WGBS years ago, during Superman's early years. It was advertised on a billboard Superman was passing.

Continuing his "Manstalker" program, he investigates the kidnapping of a little girl. Roy's detective work turned up some solid leads on her whereabouts, but he was dismissed as the "crazy television man". Angered, Roy tracked down the girl by himself, and rescued her from the kidnappers. Alfred Pennyworth sought Roy out to offer him a position on a new team of Outsiders after Batman's supposed death. He accepts that offer and becomes the costumed hero Owlman, with equipment left for that purpose by Bruce Wayne.

As Owlman, Raymond replaces Batmans deductive ability and intelligence in the group and has quite a hard, cold, exterior towards his teammates. He has grown closer to them, though, as they went through a fight with the Insiders. However, Owlman continues to find Metamorpho and the Creeper to be especially annoying.

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