Maguire, 23, started taking acting classes and appearing in commericals in 1987, and has since made numerous appearances on TV and in little-seen movies. No longer: next year Maguire will appear in his second collaboration with Ice Storm director Ang Lee, the Civil War drama Ride With the Devil, and in coveted roles in the film version of The Cider House Rules. Chatting recently with PEOPLE Online's Laura Smith Kay, Maguire sported the suit of a young actor on the rise -- inky, well-tailored, expensively casual -- but none of the attitude that often goes with it, giving each question a carefully considered answer.

Tobey Maguire: I think it would be pretty heavy if I thought of it that way. The only moment that I felt that is when [laughs] -- this is terrible -- when [director] Gary Ross came up to me and said, "OK Tobey, how are you feeling?" I was really tired that day and said, "I'm pretty tired." And he said, "I'm only going to say this to you once, and I don't want you to feel pressured, but I want you to understand the importance of it: This is a $40 million movie, and it pretty much rests on your shoulders. So do your best to get a good night's sleep." And I was like, "Come on man, I don't care what you do but please, don't tell me that kind of stuff."

PO: Did you get a good night's rest?

I don't remember. But I probably did.

PO: What attracted you to this movie?

I really liked the concept of using the black and white and color, and I liked who Gary wanted to cast -- Reese, and Joan Allen and Bill Macy. I thought that he was going to try to make a unique film and not just go the conventional way. Of course, it's both conventional and completely unconventional at the same time. I think it's a really amazing concept. He must have patted himself on the back the day he thought of it.

PO: Why do you think many people still watch those old TV shows?

I think Bill Macy's character, and how he played it could be an example of [the attraction]. His movements are so contrived and stiff, but there's still a humanity underneath that you can smell, almost. And I think that's fascinating. And for the character of David, I think it was more of an obsession to fill some kind of void he had, a sadness, and here's this utopia, this fantasy world that he could watch and gave him some peace.

PO: What did you watch on TV -- any old sitcoms like Pleasantville?

I haven't watched many shows like that myself. I used to watch all kinds of cartoons -- The Flintstones, The Jetsons. Sesame Street I loved when I was a kid. I think everybody did.

PO: What was it like to have Joan Allen as your mom in both this movie and last year's much more chilling The Ice Storm?

Working with Joan was great in The Ice Storm. She's so contained and so profesional, and she's so powerful. I love people who you undersestimate. And she's the kind of person that just surprises you, just flips me around. I remember a scene during The Ice Storm when I had to come in and say something like "I'm going to the city. I'll be back on the 11:30 train." She's got all this stuff swimming in her about her husband cheating on her, and she just says, "No, you'll be on the earlier train." I remember walking in the room, and I was 20 feet away from her, and I felt what was going on right away and I was shocked. It hit me really strongly. She's so powerful, and so helpful. It was really nice to see her laughing much more on this set, I think she felt the freedom within this character to do that.

I felt a little more comfortable to fail [working with Allen a second time]. And she's so supportive and nonjudgmental, anyway.

PO: What is it like to watch yourself on screen?

Oh that's tough, that's tough.

PO: Some actors can't even do it -- they look away.

No, I watch. One of my acting teachers told me it was very important to be able to watch yourself objectively like an instrument, so you know where you need tuning. So I do my best. The first time or two I see something I'm in, I hate it 100 percent and I cringe. I cannot disassociate myself at all. But I saw this for a third time recently and finally I was able to let go some and laugh with an audience and cry and be moved at points. It's difficult for me. I had no idea how people would react. I've never been such a big part of a film that's set to be released so wide. It was really encouraging that people were laughing a lot.

PO: Is it at all limiting to still be playing teenagers at 23?

I just look at the role. I wouldn't want to be playing teenagers 10 years from now, but it's fine. I can relate to it still. I'm not too far away. Although it's interesting, because I'm finding I look at kids and can't quite tell what age they are when they're like 13, 14 ,15. I'm starting to get confused, and I never thought that would happen to me. I'm starting to get removed from it.

PO: And you recently finished another film with Ang Lee -- Ride With the Devil. What do you play in that?

I finished that in early July. I'm best friends with Skeet Ulrich. It gets into friendships and guerrilla warfare and emancipation and love stories and big battle scenes.

PO: What kind of actress is Jewel (who makes her acting debut in Ride)?

Um, she's interesting. She really came into her own by the last couple of scenes, I saw her really finding her place and feeling comfortable to contribute. She was coming in to ten guys -- 'Ten guys and Jewel,' you could have called the film. It must have been frightening, all these guys who have been acting and this is their livelihood and its her second profession, and I think she was really scared. But she handled herself well and did a good job.

PO: What is it like to be a friend of Leonardo DiCaprio's and witness the mania surrounding him, especially the tabloid stories?

I don't know. That stuff happens to so many people and things are often misrepresented. It doesn't really affect me. I just laugh at most of it.