from Secretary
from Sherrybaby
from Happy Endings (2005 Film)
from Crazy Heart
  • Crazy Heart

    Maggie Gyllenhaal

    Maggie Gyllenhaal kissing a guy as he slides his hand up her dress and then lays her down on a bed. Her dress is hiked up and we see the guy slide his hand into her panties. We then see Maggie on her back with her dress now off, exposing a purple bra that is see-through enough to show her nipples before the guy leans over to kiss her again. From Crazy Heart.

    0:38 - 13.19 MB - 1280x544 px March 25th, 2010 @ 2:38 pm Maggie Gyllenhaal - Crazy Heart.mp4
from The Honourable Woman
from Late Night with Conan O'Brien
from Frank
  • Frank

    Maggie Gyllenhaal

    Maggie Gyllenhaal first seen having wild sex with a guy in a hot tub, dunking him under the water as she rides him while wearing a robe that gets all wet. We then see her naked as she sits in the hot tub across from the guy afterward, giving us a slightly murky view of her right breast through the water. From Frank.

    1:22 - 28.65 MB - 1280x544 px September 15th, 2014 @ 7:49 pm Maggie Gyllenhaal - Frank.mp4
from Jimmy Kimmel Live