Looks don't mean $$$$$.
They kind of do, though, don't they? In that particular profession, to say that they don't matter is naive. It's why the majority of A-Listers are drop dead gorgeous and many of them don't have long, award-laden illustrious careers. A percentage have the talent to go alongside the looks but it's just that. A select few. A large number wouldn't have 'made it' had they not looked a certain way. That's the shallow truth of it.
The fact is, some actors are better looking than they are talented - so the minute the looks fade, they start either trying to look for 'serious, dramatic' roles (see Jude Law for example) or they fade out of existence entirely(see countless other once-pretty boys who have aged into something less appealing). Some, like DiCaprio, steer away from their pretty-boy typecasting because they've got the talent to back it up. He's a rarity, though, so to use him as an example is a little unfair. He made a good choice for his career. They're not all as talented, as lucky or as savvy as that. Doesn't make them wrong, it just makes them different.
RP is moderately talented and still looks good. He looks nowhere near his age so CAN take on the 'good looking guy' roles. There are many 40 year old actors who couldn't, because they look 40 and couldn't pass for younger. If they're talented, they'll do what you suggest and move onto "middle aged guy" roles - but Ryan Phillippe doesn't look middle aged. Is he meant to 'age himself up' with make-up? Why? Half of those forty year olds are trying to look younger.
RP is never going to be a dramatic wonder, isn't going to be setting any screens on fire with his performances - but while he still has a face that's marketable he's making the most of it. Why is that wrong?
On the other hand, this might be all he's being offered. There's no shame in that. He's no Leo, never will be. He's also no Heath Ledger. Again, they're exceptions, not the norm.
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