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That's so strange. I was thinking of asking the exact same question.
I'm going to answer not so much based on my personal favourites, but on popularity, taking into account how many films they starred in during the 1990s, difficulty of the roles, acting talent and range, physical appearance, etc.
I apologize in advance for the American-centric nature of this list. For obvious reasons, American actors are just more popular.
1. Elijah Wood Starting with Paradise, he proved himself to be a remarkably talented young actor and one of the most expressive ever, capable of conveying a wide range of emotions. His career spans the whole of the 1990s, with highlights being Radio Flyer, The Good Son and (my favourite) The War.
The only thing that I find puzzling is how he could have lost all his talents in the 2000s. His sleep-inducing wooden performance in the LOTR trilogy seems to indicate that he has completely lost his touch.
2. Macauley Culkin
I almost put him at the top spot, and in terms of mainstream popularity, there's no doubt that Mac is still the king of the 1990s boy actors. No introduction necessary. Highlights: Home Alone 1 and 2, My Girl, The Good Son.
3. Haley Joel Osment In the late 1990s, HJO took over the throne as king of the boy actors. His performance in The Sixth Sense is still sited as one of the best child performances ever (though in my opinion, it's hugely overrated).
As much as I like some of his films (A.I. being my favourite), HJO always slightly creeped me out after I saw him on David Letterman and he acted like a precocious little movie star. (And these days, Dakota Fanning does the exact same thing, though she's even creepier than he was.) I prefer boy actors when they act like boys, not miniature adults. Still, there's no denying that he's up there as one of the most popular (and probably even one of the best) of the 1990s.
Highlights: The Sixth Sense, Pay It Forward (though I hate that movie), A.I. (Some of those films were made in the 2000s, actually.)
4. Joseph Mazzello Although he never achieved the same level of mainstream popularity as the top-3 actors in this list, Joseph Mazzello was probably as talented as most of them. And what he has going for him is a kind of genuine simplicity that certainly Culkin and HJO are missing with their superstar status. Mazzello always looks and acts like a real boy, with all the vulnerability and sweetness that that implies. Even in very commercial films like Jurrassic Park, where the kids are used more as props than actual chacters, his performance shines through with a real, unique quality.
5. Lucas Black Another extremely talented actor who made his name above all with the American Gothic series. Also played in The War alongsinde Elijah Wood.
6. Kieran Culkin Not as popular as his older brother Mac, but every bit as talented, Kieran took on more dramatic roles and gave some wonderful performances, most notably in The Mighty.
7. Max Pomeranc His performance in Searching for Bobby Fischer stand out (for me, anyway) as one of the best of all time by a young actor. In terms of a single great moment, of all the films by all the actors mentioned in this list, I would probably put this one at #1. The reason Max is not higher up on the list is simply that he hasn't been in that many films and his name is not that well known, even among fans of boy actors. Also, that's the only film I've seen him in. I hear Journey is not bad.
8. Mason Gamble His most famous role was in Dennis the Menace, but unfortunately that is no indication of his acting talent. Mason Gamble is mostly appreciated for having been an extremely cute blond little boy, but the truth is he was also very talented, as he proved in 1998's Rushmore. He only held a supporting role in that film, but it was enough to show us what he was capable of in terms of subtle, moving performance as an actor.
Unfortunately, he seems to have faded into obscurity after that high point in his career. He was underused in Arlington Road, and though I heard good things about his performance in the made-for-tv Anya's Bell, I've never seen it and it was never released on DVD. He was then miscast in two 2001 productions, playing characters that were much too young for his actual age.
IMDb shows that he's slated to appear in a 2006 film, after five years of absence. But, of course, he's all grown up now.
After this, it gets pretty hard to pick numbers 9 and 10. Some possible candidates:
Noah Fleiss Brad Renfro Nick Stahl Kevin Zegers Miko Hughes Joseph Cross
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