from Secretary (2002)
 
from Sherrybaby (2006)

  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal of The Dark Night fame shown bent over as a guy has sex with her from behind in a basement. We then see her breasts as she sits on a workbench topless and tells the guy that she is shaven and that he should kiss it. She then leans back as he goes down on her and we see more of her breasts. From Sherrybaby.

    1:01 - 21.29 MB - 1280x696 px October 9th, 2015 @ 12:46 pm Maggie Gyllenhaal - Sherrybaby - 1.mp4

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal unbuttoning her shirt while standing in front of a guy's desk, pulling her purple bra up to show her breasts to a guy as she tries to get hired for a job. From Sherrybaby.

    0:12 - 4.14 MB - 1280x696 px October 9th, 2015 @ 12:43 pm Maggie Gyllenhaal - Sherrybaby - 2.mp4

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal having a guy pull her shirt over her head to expose her breasts as she stands topless, turning around to show her body to the guy. She then lies down on a bed as the guy joins her and begins to kiss her. Maggie is also wearing some red panties that appear to be see-through. From Sherrybaby.

    2:16 - 47.20 MB - 1280x696 px October 9th, 2015 @ 12:40 pm Maggie Gyllenhaal - Sherrybaby - 3.mp4

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal sitting down next to a guy as she cries, leaning over to show some great cleavage before the guy reaches his hand down her dress to grab her breast. From Sherrybaby.

    Sexy 1:08 - 23.84 MB - 1280x696 px October 11th, 2015 @ 8:22 pm Maggie Gyllenhaal - Sherrybaby - 4.mp4

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal lowering her dress to reveal her breasts as a guy moves a smoking bowl around her to cleanse her. From Sherrybaby.

    0:27 - 9.28 MB - 1280x696 px October 11th, 2015 @ 8:19 pm Maggie Gyllenhaal - Sherrybaby - 5.mp4

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  • Sherrybaby

    Maggie Gyllenhaal

    World Trade Center and Stranger than Fiction star Maggie Gyllenhaal shown bent over as a guy has sex with her from behind in a basement. We then see her breasts as she sits on a workbench topless and tells the guy that she is shaven and that he should kiss it. She then leans back as he goes down on her and we see more of her breasts. Hi-res DVD capture from Sherrybaby.

    1:01 - 14.41 MB - 720x400 px January 15th, 2007 @ 4:24 pm [email protected]

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal unbuttoning her shirt while standing in front of a guy's desk, pulling her purple bra up to show her breasts to a guy as she tries to get hired for a job. Hi-res DVD capture from Sherrybaby.

    0:12 - 2.82 MB - 720x400 px January 15th, 2007 @ 4:23 pm [email protected]

    More [+]

  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal having a guy pull her shirt over her head to expose her breasts as she stands topless, turning around to show her body to the guy. She then lies down on a bed as the guy joins her and begins to kiss her. Maggie is also wearing some red panties that appear to be see-through. Hi-res DVD capture from Sherrybaby.

    1:25 - 20.01 MB - 720x400 px January 18th, 2007 @ 12:52 pm [email protected]

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal sitting down next to a guy as she cries, leaning over to show some great cleavage before the guy reaches his hand down her dress to grab her breast. Hi-res DVD capture from Sherrybaby.

    Sexy 0:46 - 10.84 MB - 720x400 px January 18th, 2007 @ 12:51 pm [email protected]

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  • Sherrybaby

    Maggie Gyllenhaal

    Maggie Gyllenhaal lowering her dress to reveal her breasts as a guy moves a smoking bowl around her to cleanse her. Hi-res DVD capture from Sherrybaby.

    0:26 - 6.15 MB - 720x400 px January 18th, 2007 @ 12:50 pm [email protected]

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from Strip Search (2004)

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal of The Dark Knight fame having a guy pull open her shirt to reveal a bra underneath. The guy then forces her to strip and she removes the bra first, holding her breasts with her hands as she takes off her skirt to reveal red panties. She then bends over to slip those off, showing her bare butt. Maggie then stands completely naked, showing full-frontal nudity with her breasts and bush in view when she drops her hands by her side. From Strip Search. Updated to higher quality.

    1:16 - 89.79 MB - 1920x1080 px November 26th, 2020 @ 10:00 pm Maggie Gyllenhaal - Strip Search - 1.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal standing nude in an interrogation room, showing bare breasts as a guy questions her, shines a light into her open mouth and then flicks her nipples with his fingers. From Strip Search. Updated to higher quality.

    1:24 - 85.83 MB - 1920x1080 px November 26th, 2020 @ 9:58 pm Maggie Gyllenhaal - Strip Search - 2.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal showing full-frontal nudity and having her breasts bounce a bit as she stands naked in front of an interrogator and then sits down on a stool. From Strip Search. From the uncut original broadcast version.

    0:08 - 3.54 MB - 1280x720 px November 28th, 2020 @ 7:38 pm Maggie Gyllenhaal - Strip Search - 3.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal showing full-frontal nudity as she sits naked on a stool in an interrogation room and a guy sits at a table across from her and asks some questions. We also see her bare butt before the guy approaches her and gives her a shirt to cover up with. Maggie offers a nice view of her breasts again while putting on the shirt. From Strip Search. Updated to higher quality.

    1:13 - 85.25 MB - 1920x1080 px November 26th, 2020 @ 9:55 pm Maggie Gyllenhaal - Strip Search - 4.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal sitting bottomless on a stool, her butt visible briefly as a guy talks to her. She is wearing a shirt that is torn open in the front so we get a view of her cleavage and some of her right nipple as well. From Strip Search. From the uncut original broadcast version.

    0:46 - 11.60 MB - 1280x720 px December 2nd, 2020 @ 2:59 pm Maggie Gyllenhaal - Strip Search - 5.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal sitting on a stool in a torn-open blue shirt that doesn't quite cover her breasts as a guy yells at her to stand up. We see her bush and bare buns as she walks bottomless over to a wall and spreads her hands against it. She is then seen fully nude as the guy runs his hands down her body, squeezing her breasts as he makes his way down. From Strip Search. Updated to higher quality.

    1:29 - 94.82 MB - 1920x1080 px November 26th, 2020 @ 9:53 pm Maggie Gyllenhaal - Strip Search - 6.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal fully nude in an empty interrogation room as she stands by the wall and then begins to trash the place, turning over the tables and chairs while stark naked. We see bare breasts, buns and bush as Maggie knocks things over. From Strip Search. Updated to higher quality.

    0:38 - 40.74 MB - 1920x1080 px November 26th, 2020 @ 9:51 pm Maggie Gyllenhaal - Strip Search - 7.mp4

  • Strip Search

    Maggie Gyllenhaal

    Maggie Gyllenhaal sitting on a stool talking to an interrogator, holding her shirt closed with one hand, wearing no bottom so we see a bit of her bush at the bottom of the frame. From Strip Search. From the uncut original broadcast version, this scene is longer than the edited version.

    1:23 - 29.12 MB - 1280x720 px November 30th, 2020 @ 3:13 pm Maggie Gyllenhaal - Strip Search - 8.mp4
 
from The Deuce (2017)
 
from Happy Endings (2005)

  • Happy Endings

    Maggie Gyllenhaal

    Maggie Gyllenhall first removing her shirt to reveal her bra, and then having sex with a guy on a bed, her right breast briefly visible as she flips over onto her stomach. Hi-res DVD capture from Happy Endings.

    1:50 - 26.00 MB - 720x304 px November 18th, 2005 @ 5:19 pm [email protected]

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from Crazy Heart (2009)

  • 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 (2014)
 
from The Kindergarten Teacher (2018)
 
from River of Fundament (2014)
 
from Late Night with Conan O'Brien (1993)
 
from Frank (2014)

  • 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 (2003)