There's plenty of wonderful children's entertainment out there. I'm immersed in it at the children's theatre all the time, so I've got loads of suggestions. I'll just rattle off the classics for you:
The Snowman is a short film based on the book by Raymond Briggs. It's a beautiful film, was nominated for an Oscar, and is basically timelessly wonderful. I don't know how much of the US it reached, but in Canada it's basically an institution. Here's a link to the
entire film on YouTube, though it's of shitty quality.
I've yet to see the DVD itself, but
Where the Wild Things Are is so good, and Maurice Sendak is the god of children's literature. The DVD has a great read-along feature. It's also got the equally good Night in the Kitchen on it, so I'm pretty sure it has to rock. Here's the
YouTube of just the Where the Wild Things Are Part of the Disk, and even though it's not the best quality here, it's still pretty fantastic.
If you truly want to ensure your boys turn out wacky, I highly recommend the brilliant, funny, smart and unnerving Canadian children's show
The Hilarious House of Frightenstein. It is the best show ever made. A kids show with Vincent Price as the host/narrator? How can you go wrong?! Looking back on this show now, I can't believe how awesome it is. There are loads of clips of it on YouTube, and you can by at least two seasons of it on Amazon. I have fantastic memories of the unnervingly creepy characters and the total insanity of that show! Wolfman Jack? Did they
want us to grow up to do drugs?
My SO would hate me if I didn't recommend Fraggle Rock - they've got seasons 1-3 out on DVD, and we've got all three. He's watching season 3 right now while he washes dishes. These are more his thing than mine, but he just loves it. And granted each episode teaches important lessons about kindness, compassion and acceptance.
If you wanna talk Jim Henson, I recommend the fantastic DVD collections of
The Storyteller series. This is basically the high art of Jim Henson at it's best, and you've got some unbelievably brilliant actors along side fantastic creatures of Jim's creation. So damn, damn good. Great for kids, and the quality of these sets is bar none. If you want to save money, just get "the Complete Collection" - the second collection of Greek Myths is not
quite as strong, but is still great.
I could go on for a lot longer, but these are probably my top pics for kids your son's age, and they're all timeless enough that he and his future lil' brother will enjoy them.
Edit: Oh, I almost forgot:
The Dog Who Stopped the War (aka La Guerre des tuques) is a brilliant French Canadian film dubbed into English about kids who build a giant, fantastic, unbelievably awesome snow fort, then go to war over it's owner ship. It addresses, quite deeply, the concept of war. The war is ended when part of the fort caves in and kills one of the children's dogs. It's a surprisingly frank, deep exploration of war and loss from a child's perspective. I saw it when I was about 7, just before my first experience with human death when my grandpa died. It was very useful in helping me understand loss.