George Clooney is almost 50, but he’s certainly aging well (as if I’m the first to notice). I don’t think I would have given a 20-something Clooney a second look – it could just be the hairstyle, but I think his eyes look better with wrinkles.
I had not thought about her for a long time, but here in Salt Lake, they recently began airing re-runs of the (very mediocre) sitcom “Still Standing” and I am struck at how truly stunning Jami Gertz is…
I always thought she was attractive back in the 80’s in movies like “Less Than Zero” or “Lost Boys” but she seems (to me at least) to have really come into her own in her late 30s/early 40s. She is not quite as slender as she used to be, and I think she looks better than ever now.
(I am a bit surprised she was involved in a show like “Still Standing”—if you have never watched it, know that she is about the only redeeming feature of the series)
Kate Winslet looks more self-possessed now than at 19 in the days of Titanic. Of course, she was 19 and in the biggest movie ever, so that’s surely a part of it.
Jonathan Rhys Meyers looks better now, even with his apparent alcohol problems, than he did ten years ago, when he was affecting this waifish, long-haired rent boy look that was really unappealing and chickenhawk-baity. Yuck. He’s far too gorgeous for that.
And how about the silver foxes? Mark Harmon is sexier as Jethro Gibbs on NCIS than as the sex symbol of St. Elsewhere, Mark Caldwell. His replacement as resident hottie on St. Elsewhere was Bruce Greenwood, who is still pretty damned smoldering as Captain Pike in Star Trek. And pundit Keith Olbermann is a far more handsome man than sportsanchor Keith Olbermann. Perhaps especially when he keeps his mouth closed.
Weird. I was thinking of her as an example, but I was going to use Seinfeld as an example of when she was unattractive. Given how good she looked on, say, Arrested Development, or even now, I wondered if they purposely uglied her up on Seinfeld as part of her character. She has such beautiful hair and it’s totally wasted with how she wore it on Seinfeld.
To add: I saw some pictures of Monica Belluci when she appeared to be in her early 20s. She was certainly attractive, but not striking like she was in her mid 30s.
Jennifer Aniston. At the beginning of Friends she was simply pretty, now she’s really hot
Julia Louis-Dreyfus has naturally curly hair, something that professional hairstylists around the U.S. have major problems with. Her hairstyling, or lack thereof, on Seinfeld was a representation of that. Her hairstyling now is also a representation of that – it’s not styled as is, but straightened first.
Melissa Gilbert was wholesomely plain as a child actor and seemed to be stuck at that “awkward” stage waaay into her 20’s. ( Of course, next to Rob Lowe, anyone would come off badly!) Now she’s in her 40’s, had some work done, and is quite strikingly attractive, IMO.
My God! She was pretty as a kid but then I saw her on ST:TNG and I said, “She looks like our friend H. when she hits that age.” Except H. didn’t and had to settle for looking like Julia Roberts’ sister–you know, the one with a figure?
I confess that I dismissed Billie Piper when she was a kid. She’s starting to grow into her face.
Anyway, I’m an old fart and I like a few unaltered miles on the chassis.
Again, as an old fart, those look a little too modern. 
James Marsden
I’d seen him some older movies like Gossip and Disturbing Behaviour but I never thought he was sexy back then. Too girlie looking for my tastes. Then when I saw him in Hairspray I thought “Wow, Jimmy has really grown up. He’s a hunk now”.
So much hotter in his old age(he’s 36).
Sandra Bullock has been making the talk show rounds lately. She’s gone from cute to stunning in the last few years.
I was going to mention him. I saw a clip once of him in Roseanne and he made me think of an extremely well-made inflatable doll; he just didn’t look real.
Clip here
I came in here to mention that Roseanne-era Clooney was goofy-looking…definitely cute, but not the World’s Sexiest Man by any stretch. He is hotter now than he was then.
Just to be contrary: too many Hollywood starlets start out at a comfortable weight, but then as they age, decide to become skeletons, probably because they think it will make them look younger. It doesn’t. Cameron Diaz looked amazing in The Mask, looks dreadful now. Courtney Cox is another example.
I think the Britney Spears of 2007 is much sexier than the Britney Spears of 2000. In other words I think she looked better during the period in her life when the entire media and internet was lambasting her as “fat” and “trashy” than at any other point in her career.
Catherine Zeta-Jones.
I win!
Nicole Kidman.
I was going to say the same thing. This is very noticable on TV. An actress will be attractive in season one, then by season two will look scrawny and unhealthy.
No way. The opposite in fact.
She was incredibly hot in Dead Calm and Days of Thunder.
Now she looks very odd and plastic.
Wow. I totally forgot she was in Much Ado About Nothing. And you’re absolutely right - she’s stunning now, while she was merely adorable a decade ago.