[2] The strip told the adventures of a well-meaning hobo who encountered a lot of misfortune and bad luck, partly because of his appearance and low position in society, but who did not lose his smile over it.

The archivist Jennifer Huebscher wrote that Opper may have taken inspiration for the Happy Hooligan's look from an illustration done by cartoonist Oscar Bradley depicting a Minnesotan acrobat and vaudeville entertainer named Fred Lowe.

Starting June 23, the strip was called Dubb Family, and didn't feature any appearances by Happy Hooligan; this title lasted until September 29.

In 1902 a music supplement of Hearst's Chicago American featured Happy Hooligan's Reception march and two-step by Richard A. Wilson and lyrics by Curtis Dunham, with artwork by F. Opper and R. Dirks.

In 1907 Inter-mountain Republican of Salt Lake City published a piano dance and two-step by Theodore J. Morse titled Happy Hooligan.

[17] The strip is referenced in Beverly Cleary’s 1961 novel Emily's Runaway Imagination when Mr. Archer is described wearing an tomato soup can tied to the top of his head like Happy Hooligan does when attending the Hard Times party.