Sherrybaby (2006)

What was independent skinema before Maggie Gyllenhaal came along? Ever since her kinky nude debut in Secretary (2002), Jake’s searingly sexy sister has been an absolute stand-out in a host of skintastic flicks. Breast of all, many of her provocative parts have prompted Maggie to peel down. If you don’t believe us, check out Strip Search (2004), Happy Endings (2005), Frank (2014), The Honourable Woman (2014), The Deuce (2017-2019), and The Kindergarten Teacher (2018). Of course, we’d be remiss not to include SherryBaby (2006) on this list. Thanks to the writing and directing of Laurie Collyer, this R rated pic picked up a lot of praise. The drama swept at the Stockholm International Film Festival where it won Best Film and Best Actress! Maggie plays a rough-edged New Jersey woman who gets out of prison and tries to reestablish a relationship with her young daughter. Her attempts to connect with other adults, however, frequently involve illicit sex. As such, we are treated to views of Maggie’s nude boobs when she gets banged in a basement just 12 minutes into the movie. The panty-clad cutie continues to flash her flesh. In fact, she shows off her rack at the 21-minute mark. At the risk of repetition, Maggie’s mams also appear when a dude relieves her of her shirt. How kind of him! Later, Maggie loses her top again. No wonder the 41st Karlovy Vary International Film Festival gave Ms. Gyllenhaal the Crystal Globe/Grand Prix. Heaven knows her globes give us grand pricks too!