Bob Hoare was born in 1942, and recalled that "when I was a child I used to draw all the time": "My parents were worried that I didn't go out enough because I was always staying at home drawing." They tried to dissuade Hoare from following a career as an artist, and his father, who was in engineering, would not allow him to attend art college. He went instead to a technical college to train as a mechanical engineering apprentice.
Hoare's early work was as a technical illustrator, but he also freelanced for a number of sports and musical publications. In 1997 Hoare was contributing to a number of publications, including the Portsmouth Evening News, and decide to become a full-time freelance. By 2002 his work was syndicated by Graphic News, and he was also producing caricatures for "Passing Shots", a weekly column appearing in the Southern Daily Echo.
In 2002 Hoare described his method of caricature: "First of all I get a picture of the person I am drawing out of a magazine or off the Internet, and then I scribble away trying to get a likeness of the character. Once I am happy with the rough, I will use it as the basis for my picture and I will then trace it off onto the paper, which is Italian board."
- Dave King "An illustrated man", UK Newsquest Regional Press - This is Hampshire, 1 November 2002.