Sheila Schafer ("Lady in Diner"), actual resident of Medora, North Dakota, has one line in Wooly Boys (2001) with Peter Fonda. Sheila has coincidentally stated that her husband, Harold Schafer, who restored Medora in 1964, had one line as an extra in Das war der wilde Westen (1962) with Henry Fonda.
Sheila Schafer ("Lady in Diner") stated that she hated the make-up she had to wear "to look like an old woman, because I wasn't old back then!"
While a great majority of the filming is credited to Medora, North Dakota, filming was also done in Fryburg, North Dakota (13 miles east of Medora) and Beach, North Dakota (27 miles west of Medora).
The film cast includes one Oscar winner: Keith Carradine; and two Oscar nominees: Peter Fonda and Kris Kristofferson.
Joseph Mazzello's first film of the 2000s.