The Good Girl (2002)

"The Good Girl" is a 2002 indie drama set in a small Texas town, following a discount store clerk whose affair with a younger co-worker disrupts her stagnant life. Jake Gyllenhaal plays that co-worker, the one audiences remember for stripping the character's awkwardness into something physical on screen. The site holds 2 scenes from the film showing his character's affair play out in bed, with nudity included. Gyllenhaal was in his early twenties when this came out, years before his name carried the weight it does now.