The story at Willys-Overland for 1939 is a complicated one, with three different cars in production marketed under two different names: Willys and Overland.

The 1930s was a rocky decade for Willys-Overland, the beleaguered Toledo carmaker.  The high and low points included near-collapse, bankruptcy, and the cancellation of its existing automobile lines in 1932, the introduction of the unorthodox, narrow-gauge Willys 77 in 1933, and the more conventional but still compact Willys 37 in 1937. The roller coaster ride continued in 1939 when the automaker had three different car lines in production: the Model 38, Model 48, and the Model 39 Overland. Let’s sort them out.

As the name suggests, the 1939 Model 38 (above) was simply a carryover of the 1938 Willys, which in turn was a minor update on the 1937 Willys 37 styled by Amos Northup. (See our feature on the Willys 37 here and our bio of Northup here.) In fact, the production figures for the ’38 and ’39 versions are consolidated. Then in November of 1938, the Model 38 became the Model 48—again, with virtually no changes, except that it was offered only in standard trim. The deluxe trim level was dropped to make room for the company’s new premium entry.

In October of 1938, Willys-Overland introduced its new flagship, the Model 39 (above), reaching back into the past for the name Overland to market the product. Founded in 1903, Overland became Willys-Overland in 1909 under the leadership of John North Willys, while the Overland name was last used on an automobile in 1926. The Overland script was featured on the hood and in company advertising, but it failed to catch on as consumers were stuck on the Willys name. So in mid-production, the hood badging was changed to Willys-Overland. The Overland experiment lasted less than one year.

Northup died in February of 1937, and reportedly, the Overland’s dramatically styled front end was the work of Willys-Overland’s Toledo design crew. Still, Northup’s influence can clearly be seen: There’s a striking resemblance to his Spirit of Motion theme for the 1938 Graham, better known as the Sharknose. However, from the cowl back, the body shell is Northup’s Willys 37 design. Three body styles were offered—coupe, two-door sedan, and four-door sedan—in three trim levels: Standard Speedway, De Luxe, and Speedway Special, in ascending order.

For the Overland, there were significant changes inside and underneath to go along with the radical styling. The wheelbase was lengthened from 100 to 102 inches to improve the ride, and the mechanically operated 9-inch brakes were exchanged for 9-inch hydraulics, with the hubs and wheels upgraded from four lugs to five. But the biggest improvement was in the engine, boosted from 48 to 60+ hp through clever refinements by W-O chief engineer Barney Roos. (See our feature here.) It was this same rugged inline four that powered more than 600,000 Willys and Ford Jeeps through World War II.

Despite all the product improvements offered in the Overland, Willys-Overland did not enjoy a successful 1939 season. The year before had been rough enough with around 26,000 cars sold, but in ’39 the volume fell another  31 percent to 18,000—due in part, we can guess, to the multiplicity of models and the confusion over model names. The company reverted to a single brand under the Willys name for 1940, but its fortunes didn’t turn around until the U.S. Army adopted the Jeep.

Overland Sedan with the Twentieth Century Limited