Ryan Phillippe got his start in the early 90s playing US daytime television’s first gay teenager, Billy Douglas, on One Life To Live. With his short blond curls and loin-tingling eyes, this hunky heartthrob went on to star in a slew of teen blockbusters that cashed in on his ability to play cynical, sexy leads who weren’t afraid to show some skin. Ryan will have you crying and biting your pillow when you see his rear view debut in the tense drama Little Boy Blue (1997). In 54 (1998), a drama based on the world-famous Studio 54, raunchy Ryan wears precious little attire, strutting around in a Speedo, showing off his gym-built upper body, and beautiful bubble butt, a fantastic feat he did again in Homegrown (1998). We were treated with another flash of ass in his most famous roll to date as the seductive Sebastian in Cruel Intentions (1999). He’s got such a hot ass that it would be more than cruel of him to keep it covered and apparently Ryan agrees with our assessment, because he busted out his bunnage in 2007 on the boob tube drama Damages and in his directorial debut Catch Hell (2014). Now that’s an behind that will have you damaging a lot of underwear!