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Ryan Phillippe
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Wednesday, October 1, 2025
ACTORS & Skin: Ryan Phillippe
Shortly after being signed with Cathy Parker Management, actor Ryan Phillippe was cast in his first professional role playing Billy Douglass on the ABC soap, One Life to Live. Phillipe played Billy starting in 1992 and left in 1993. At the time, Billy was the first openly gay teenager to ever appear on a daytime soap opera.
After leaving the soap, Phillippe appeared in a number of TV movies and guest appearances on shows including; Matlock, Chicago Hope, Perry Mason and the Canadian drama Due South. The young actor's star really began to rise in the mid-nineties with roles in Crimson Tide and White Squall. From there the rest is history.
The late 90's were Phillippe's hottest years in film with his roles in 54, I Know What You Did Last Summer and Cruel Intentions. These were also the years Phillippe became one of films hottest sex symbols, helped by the many appearances of his spectacular butt on the big screen.
I've always appreciated Phillippe's seemingly openness to being a sex symbol. He never seemed to shy away from photoshoots or movies that required him to show a little skin. The actor even seemed to be making fun of his many 'butt baring' scenes in some roles, including his turn in MacGruber. (clip above_
Phillippe never seemed to show of his glorious physique, in films, in selfies on social media, and of course the thousands of shirtless paparazzi pics. For those eagle followers of Phillippe's career, you also know he had a few nude images and videos leaked several times over the years. Check out more of Phillippe's nude resume in the posts below.
Thanks to SOMS (Scenes of Male Skin) for some of the images and clips
Damages
Ryan Phillippe: The 1990's (Part 1)
Nineteen-year-old Jimmy' s dad is a vicious, impotent Vietnam veteran who forces his wife and son to have incest. He has a secret he'll kill to keep. Jimmy won't abandon his two kid brothers by leaving.
Actor Ryan Phillippe's first nude scene was the provocative love scene below from 1997's Little Boy Blue. This is also the first of several scenes in which Phillippe plays characters forced to get naked at gunpoint. In Little Boy Blue it's his father holding the gun.
It's an rather strange, but also erotically vulnerable theme to have a hot young actor forced to strip, or have sex at the hands of older man wielding a gun. The theme occurs in at least 3 of Phillippe's films.
Homegrown (1998)
Three marijuana farmhands see their boss killed, ending their peaceful existence in NW California. They decide to harvest, process and sell the crop themselves. Crime bosses, corrupt cops, killer pilot, greed etc. ensue.
It's also a man with a gun who forces a naked Phillippe out of bed in 1998's Homegrown. The scene is rather disturbing, but again, erotically compelling given the vulnerablity themes, the cfnm /cmnm elements, and of course, hot hot the young actor.
Ryan Phillippe: The 1990's (Part 2)
The famous 1970s New York City nightclub seen and told through the eyes of a young employee.
Although I know it's a weak, and often flawed movie, 1998's 54 is one of my favorites from actor Ryan Phillippe. I think I love the 'fantasy' that is 54, and how it brings to life so much of what I've read about the club over the years. I did a previous piece on the club, and it's famous guests and party life on FH HERE:
I also really liked the music, and the 'naive' guy hits the big city theme. Although, we quickly learn that studly Shane O'Shea seems to know exactly what's he's doing. 54 and Cruel Intentions are also favorites because of those iconic Ryan Phillippe butt scenes. There also famous for the scenes, including additional butt scenes, we didn't see.
Writer and director Mark Christopher released a director's cut years after the original 1998 theatrical release. There were several additional scenes including a second butt scene, (below) when Shane was on the rooftop. There was also more material about Shane's sexual relationship with men, including more of his 'kiss' with Greg. (Breckin Myer)
Most interesting to me, was the edit of the butt scene below. If you watch the clip, you'll first see the original scene that appeared in the theatrical release. If you continue to watch, you'll see the edit from the director's cut. The edit of the director's cut includes Shane in bed with both men and woman, in fact it's a man in bed as Shane gets out of the bed naked.
Cruel Intentions (1999)
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
I don't think Phillippe was ever hotter than when playing Sebastian Valmont in 1999's Cruel Intentions. The movie was a complex erotic mind field, and so much fun to watch. I'm so glad I saw it in the theatre's when it first came out. I wish last year's television adaptation had stuck around. It wasn't nearly as fun as the original film, but it had it's moments, and needed more time to grown.
Like 54, director Roger Kumble, also tragically let a butt scene from Phillippe stay on the cutting room floor. The scene takes place just after the one shown in movie, after Sebastian exits the pool. Oh, how I would love to have seen the scene in HD, especially as Phillippe is moving in this scene, walking up the stairs to exit the pool. At least we have the raw footage to enjoy.
Ryan's Rear & the Curious Case of Catch Hell
'A fading Hollywood pretty-boy gets taken and brutalized in Louisiana by two local men with his total ruination at heart.'
With a focus on men in the media, I often come across scenes in which the nudity stems from depictions of violence, sexual abuse and rape. I usually try to avoid those scenes as I'm especially comfortable with sexualizing acts of violence and cruelty. That was the case when I first saw the nude scene from the film Catch Hell. (aka Chained)
In the 2014 thriller, Ryan Phillippe plays actor Reagan Pierce, a actor's who's career is on down slide, and who heads to Louisiana to film a new film. Things take a turn quickly, with Reagan soon kidnapped, chained and tortured by his kidnappers Mike and Junior. Turns out, the kidnapping, as well as Reagan's torture and humiliation is payback for an affair Mike believes the actor had with his wife.
As the film goes on, we see that Junior (Stephen Louis Grush) has a wee crush on the hot blonde Adonis chained in front of him. Reagan senses it as well, as uses it to try get on Junior's good side which doesn't exactly end well. Near the end of the film, Junior, thinking Reagan's out cold from a pain pill, attempts to rape him. Reagan, awakened by a phone, fights off his attacker, and Junior ends up being dragged away by one of his pet gators.
I chose to not initially write about the film, due to the attempted rape, but given it was another butt baring from Ryan Phillippe, it was difficult to ignore. I found it fascinating that Phillippe would take this role, given his Hollywood history. Phillippe is a good actor, but it can't really be argued that his incredible looks were a huge part of rise in films, especially during the nineties. It also not a secret, Phillippe has a large gay following. In part, this was due to his ground breaking role as a gay teen on One Life To Live, but a another big part were his butt baring scenes in Little Boy Blue, Cruel Intentions and 54.
It was fascinating to me, that the actors would be so vulnerably exposed in Catch Hell, especially after learning the film was written, produced and directed by Phillippe himself. Although I don't find violence the least bit sexual, Catch Hell went out of it's way to ensure Reagan's hot body was frequently in focus. The kidnappers found nude shots of the actor and his female sex partners on his phone, (which they released to the press) and being chained up, Reagan was humiliated even further needing Juniors help to pee.
Phillippe directed the attempted rape scene in a way to ensure his butt got exposed not just to Junior, but to the audience, even having Reagan's butt visible through Junior's legs as he took off his pants. These choices, although gratuitous (which isn't always a bad thing) would have felt much more exploitative if I hadn't known Phillippe not only wrote, but directed the nude scene itself.
The film has been both impressed, and curious at about the actor, and in this case, the writer and directors creative thought process. I've tried to find an interview where Phillippe discusses his motivation, but only found a few where he talked more generally about getting his first feature off the ground.
In many ways, it feels like Phillippe is purposely using, and even mocking his reputation, and taking on how the industry, and social media can drive and often, ruin a career. I wouldn't go so far as saying 'Mike' and 'Junior' represent Hollywood and the industry, but it's an interesting parallel. In Catch Fire though, many try to fuck him over but ultimately, the actor fights back.
In the 2014 thriller, Ryan Phillippe plays actor Reagan Pierce, a actor's who's career is on down slide, and who heads to Louisiana to film a new film. Things take a turn quickly, with Reagan soon kidnapped, chained and tortured by his kidnappers Mike and Junior. Turns out, the kidnapping, as well as Reagan's torture and humiliation is payback for an affair Mike believes the actor had with his wife.
As the film goes on, we see that Junior (Stephen Louis Grush) has a wee crush on the hot blonde Adonis chained in front of him. Reagan senses it as well, as uses it to try get on Junior's good side which doesn't exactly end well. Near the end of the film, Junior, thinking Reagan's out cold from a pain pill, attempts to rape him. Reagan, awakened by a phone, fights off his attacker, and Junior ends up being dragged away by one of his pet gators.
I chose to not initially write about the film, due to the attempted rape, but given it was another butt baring from Ryan Phillippe, it was difficult to ignore. I found it fascinating that Phillippe would take this role, given his Hollywood history. Phillippe is a good actor, but it can't really be argued that his incredible looks were a huge part of rise in films, especially during the nineties. It also not a secret, Phillippe has a large gay following. In part, this was due to his ground breaking role as a gay teen on One Life To Live, but a another big part were his butt baring scenes in Little Boy Blue, Cruel Intentions and 54.
It was fascinating to me, that the actors would be so vulnerably exposed in Catch Hell, especially after learning the film was written, produced and directed by Phillippe himself. Although I don't find violence the least bit sexual, Catch Hell went out of it's way to ensure Reagan's hot body was frequently in focus. The kidnappers found nude shots of the actor and his female sex partners on his phone, (which they released to the press) and being chained up, Reagan was humiliated even further needing Juniors help to pee.
Phillippe directed the attempted rape scene in a way to ensure his butt got exposed not just to Junior, but to the audience, even having Reagan's butt visible through Junior's legs as he took off his pants. These choices, although gratuitous (which isn't always a bad thing) would have felt much more exploitative if I hadn't known Phillippe not only wrote, but directed the nude scene itself.
The film has been both impressed, and curious at about the actor, and in this case, the writer and directors creative thought process. I've tried to find an interview where Phillippe discusses his motivation, but only found a few where he talked more generally about getting his first feature off the ground.
In many ways, it feels like Phillippe is purposely using, and even mocking his reputation, and taking on how the industry, and social media can drive and often, ruin a career. I wouldn't go so far as saying 'Mike' and 'Junior' represent Hollywood and the industry, but it's an interesting parallel. In Catch Fire though, many try to fuck him over but ultimately, the actor fights back.
Originally posted May 2020
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