Hollis T. Mason was the first Nite Owl, working as part of the Minutemen in the 1940s. When he retired in 1962, Daniel Dreiberg sought him out and asked if he could don the persona to fight crime — Dreiberg then became Nite Owl II. He later met Rorschach and the two of them became a crime-fighting duo and good friends.
During the events of Watchmen, he became romantically involved with Silk Spectre II (Malin Akerman) after she broke it off with Doctor Manhattan (Billy Crudup). By the end of the movie, they ran off together under new identities because they were presumed dead in Ozymandias's (Matthew Goode) attack on New York City.