If you live with teenager boys, a sure way to get them interested in helping you to carve pumpkins is to go with a science fiction theme.
Let them reproduce their favorite character, robot or space ship. Wired magazine runs last year a contest. The big winner was a Death Star Pumpkin carved by the super talented Noel Dickover of Centerville, Virginia.
If you wish to make your own, Noel published a tutorial on how to carve the Death Star from Star Wars. I am impressed! Technically, The Death Star is a hybrid between a pumpkin carve and a pumpkin sculpt. Allow between 4 to 10 hours to make it.