Headline Harry and The Great Paper Race is an educational game about historical events of 20th century United States.
As a new reporter for Headline Harry, the editor of the US Daily Star, the player must prove themselves by going out and getting the story fast and right. Opposing the player are Marvin Muckraker and his reporters for the Diabolical Daily, a sensationalistic tabloid paper, whose stories are quite funny, as they mix the facts of various stories up into one. The player travels from place to place all over the USA, getting leads on stories from 1950-1990, such as the NASA moon landing or the Beatles' appearance on the Ed Sullivan show.
The game offers several assignments, each of which has the player chasing a different story. In each location, the player can talk to people, read books, listen to the radio, or listen to recordings on a tape. Each of these actions will typically give the player vital facts about some event, which need to be gathered in their trusty notebook. To make matters more difficult, these facts can pertain to several unrelated stories, and it's up to the player to identify which story they should focus on. Once the player has discovered and entered all the key facts — a year, a date, a location, an event, names of key people, and key words — the story can be filed, rewarding the player with an article that describes the historical event accurately.
However, each assignment has a time limit, consumed by traveling and fact-gathering. Should the player run out of time, he will instead be presented with the Diabolical Daily's nonsensical article that mangles the historical facts. Time can also be lost by random events, and regained by finding items dropped by the competing reporters.