100 Hot Men and a Dame: #79 Ryan Phillippe

79. Ryan Phillippe

Occupation: Actor

Nationality: American

Age: 37

Best Known For: Late 90s teenage heartthrob who grew up to become Mr. Reese Witherspoon for a time and a pretty decent actor (Stop-Loss).

The first of the Lost Entries of the 100 Hot Men and a Dame series makes its debut today! Perennial contributor Dave helps me out again to discuss DILF Ryan Phillippe. I'm presenting the post as it was originally written months ago, but it should be noted that I have now seen Cruel Intentions properly and not only is Ryan's ass damn fine but it's probably the crowning achievement of his acting career. Severely underrated.

Dame James: When did you first encounter Ryan and, if it wasn't love at first sight, when did you fall in love with him?

Dave: I first saw Ryan in Cruel Intentions. I was only 10 or 11 when it was actually released, but thankfully for my lustful hormones, I didn't see it until a few years later, which meant I FULLY appreciated him in it. I mean, that butt shot is still the talk of the gays over twelve years later! I mean, it may actually be the most perfect bum of them all, and you know I was going on about Rafa's when we discussed Andy Roddick (who also has a nice bum. OH GOOD LORD.). I know we're going into more cerebral reasons behind attractiveness here, or at least less shallow, but pure horny attraction to physicality is undeniably the driving force behind this countdown and well, with Ryan, it mostly is about the robust, muscular curves of his bottom and arms and chest and oh I'll be back in a moment...

ANYWAY. Looking at Ryan's filmography, he hasn't actually been in that many films of much interest - when The Lincoln Lawyer is your most prominent credit of the last three years, you can see he's lost interest in acting. But he was superb in Stop-Loss - finally proving that he has a vulnerability and depth to him, which was rather a revelation, although I'd wager that his cruel game-playing with Sarah Michelle Gellar in Cruel Intentions was almost as much of an acting coup, because not everyone can do it with such panache.

I'd also like to note how, despite the perfection of the arse circa-1999, Ryan seems to have really found his sweet spot around recent years. The behind might have been fine, but I always found him a bit off somehow - perhaps it was the Justin Timberlake hair. But photos in the past few years have just shown, to me, human perfection - a sculpted, relaxed face, strong shoulders, and a musculature that's not overdeveloped but still screams "MAN!"

DJ: I'm pretty sure I first saw him in Cruel Intentions in the severely edited version they show on TV, and I was never that into him. He was rather frail with features that were perhaps a touch feminine; in other words, he was a true teenage heartthrob. He also had that late 90's vibe around him which is great for nostalgia but maybe not the sexiest look ever. But perhaps if I had gotten a VHS copy and saw the butt scene for myself, maybe I would have come around on him sooner. I've still never seen the scene for myself, but I have seen stills, and Holy Jesus what a glorious ass! I love how it stands out and makes a statement against his (then) skinny frame. It's not ridiculously large but it's big enough that it makes you go "Dayummmm" every time you look at it.

It wasn't until the time of Stop-Loss that I realized I was attracted to Ryan. You talk about how this countdown is designed to discuss attractive men and what makes them so desirable beyond their surface features, and for the most part that's true. But when it comes to Ryan, there are no cerebral reasons why I'm attracted to him: it's pure, animalistic lust. He was fine in Stop-Loss and I'd wager as well he's probably a lot better than we ever gave him credit for in Cruel Intentions. But besides Igby Goes Down, where he really turns up the preppie rich boy machismo, there's really not much of note in his filmography. It's mostly a lot of mediocre rolls in would-be prestige pictures. Without the work to back him up, it's all about that ass. But I don't think this is necessarily a bad thing. It is better to be famous for something superficial than to not be famous at all.

D: That photo is absolutely transfixing. Yes, let's abandon pretense - I'm going to focus on the physical details. The nipples there are just so small and alive! The six-pack that isn't outrageously defined but enough that you know you could probably punch it and your hand would hurt. The vague stubble. And he's clearly in the middle of a 'fuck you' walk where he ignores everyone in his path. (I do those a lot. Sadly I never look like this while doing them.)

Looking at other photos, I think he really needs the stubble - he looks too small without it, a bit meek. I think it really gives him that extra swagger. I'm glad he figured out that the curls in his hair really don't suit as well - short back and sides really work here (hence the perfection of being cast as a soldier).

DJ: I believe that it was after he divorced Reese Witherspoon that he got super hot. I'm really starting to think she is the Devil in human form because she not only held him back from reaching his full hotness potential, but she also stunted Jake Gyllenhaal there for awhile. What is her problem, exactly? Do you think she doesn't get enough satisfaction from her millions and resorts to taunting us little people to pass the time?

D: Ryan and Reese were kind of a nice normal couple to look at while they were together, but I never really thought about them at all. And you're right, it really was once they split that he came to proper fruition. Almost as though she was holding him back in those teenage roles, so only when he broke away from that did he figure out he was all grown up. I don't know what it is about her, there must be something in that chin...

DJ: Once he ditched his late 90's pretty boy look, I think he truly discovered his sexiness. Which is a rarity, as only a select few men find their hotness peak as late in their career as Ryan did. I guess fatherhood and ditching the Pointy Chined One (seriously, her chin must have been named in the divorce suit as one of the causes for irreconcilable differences) really suited him in the looks department.

D: I see Ryan's going to be making a move usually reserved for prolific actresses and heading for TV - a guest spot on Damages! It probably would've be a better move if the show hadn't been forced to move channels, but I hear they can swear on DirecTV? So maybe he'll take off some clothing. I may have to catch up.

DJ: I had not heard he was appearing on Damages! How positively exciting! I haven't seen the fourth season yet, due to it moving to a channel I don't get, but I was absolutely enthralled with the first three seasons. And the show has a great track record with late 90's teen stars transitioning into sexy maturity, particularly in the second season when they had Matthew Davis and Timothy Olyphant (sigh) on the show. He's actually a brilliant choice for the show, as his penchant for preppie upper class snobs is a perfect fit for Damages. And if he's even half as sexy as Olyphant was on that show--and trust me, Damages objectified Olyphant brilliantly--then watching it will be time well spent.