Two-time Academy Award winner Hilary Swank has the ultimate rags-to-riches story. The high school dropout briefly lived in a car with her divorced mom before making her big screen debut in the horror flick Buffy the Vampire Slayer (1992). After appearing in The Next Karate Kid (1994), the ambitious ingenue began to land sexier film roles in Sometimes They Come Back…Again (1996), Kounterfeit (1996), Quiet Days in Hollywood, Dying to Belong (both in 1997) and Heartwood (1998) which included a nip-slip! As soon as Hilary completed a brief stint on the Fox hit Beverly Hills, 90210 (1997-1998), she scored her breakout part as a transgender man in the heralded biopic Boys Don’t Cry (1999). In addition to baring her breasts and butt, the complicated character pulls on a pair of Fruit of the Looms—exposing just a hint of her pubes of the poon! If that’s not hot enough, the hottie also makes out with a topless Chloë Sevigny which resulted in Swank taking the Oscar!

Since then, Hil’s hills have mostly remained under wraps even though she showed cleavage in The Affair of the Necklace (2001), displayed her pokies in Getting Naked (2003), and sported sports bras in Million Dollar Baby (2004), which brought her a second Oscar. Check out her sexy victory gown in Oscar Countdown (2005). Audiences were thrilled to see Hilary’s nude booty in the thriller The Black Dahlia (2006) and her bra-clad rack in the chick flick P.S. I Love You (2007). Yet the breast came with The Resident (2011) since the movie featured its star in skimpy skivvies. It also showcased her (or her body double’s) three Bs! Titillating turns in Camera Shy (2012), You’re Not You (2014) and What They Had (2018) followed, as did a chance to show off her mams and muff while banging Tommy Lee Jones in The Homesman (2014). That must make him the Bonesman!