Gyllenhaal had more success starring opposite Jennifer Aniston in The Good Girl, which premiered at the 2002 Sundance Film Festival; he also starred in Lovely and Amazing with Catherine Keener.
Gyllenhaal havde mere succes, da han spillede over for Jennifer Aniston i filmen The Good Girl, der havde premiere ved Sundance Film Festival i 2002; han medvirkede ligeledes i Lovely & Amazing med Catherine Keener.