Robert Craig Hupp was a veteran of the auto industry by the time he decided to build his own car. Having worked at Olds, Ford, and Regal, he began experimenting on his own, and by the beginning of November 1908, he had completed a two-seat runabout with a four-cylinder water-cooled engine. Introduced at the February 1909 Detroit Automobile Show, it was designated the Hupmobile Model 20. Priced at $750, it undersold the Model T Ford. Production began in March at the newly organized Hupp Motor Car Company.
First-year sales were impressive—1,618 cars—and more than tripled in 1910. Three additional body styles were added for 1911: a two-passenger torpedo, a four-passenger touring car, and a four-passenger coupe. Joined by a larger Model 32 in 1912, the Model 20 remained in production through 1913, by which time a long-wheelbase version was available.