Great list and well thought out. Really gives a wide range of Miyazaki styles and... shall we say intensity levels? Spirited Away really is amazing, but it's WEIRD. And Totoro is great, but coming after Spirited Away its slowness might be something of a shock.
He proposed two alternative lists, which I really really liked and had to share here (partially for my own dog fooding and partially because it was worth sharing).
Tim's lists provide two routes: one to ease you into it, and one to jump in the deep end. Here are his lists and comments regarding them.
The "Ease In" List
If you want to start with movies that are more accessible to Western viewers, then try this.
**The Wind Rises **- It's got more realism than many of the others.
Kiki's Delivery Service - Low-stress plotline, but mixes fantastical elements into a normalish setting. And it's super adorable.
**My Neighbor Totoro **- After Kiki's Delivery Service, Totoro lowers the intensity even more. Pretty much nothing happens. Safe for toddlers but artistic enough for parents.
**Ponyo **- Now that you've got a feel for Miyazaki's world, let's introduce more of the strangeness but keep the cuteness. This is a loose retelling of The Little Mermaid.
Castle in the Sky - This is a good transition between the light material and the heavy material.
The "Strange and New" List
If you are up for just seeing something strange and new. Then this list might work better.
**Spirited Away **- Sean's right about this being a good first viewing. It's pretty thoughtful and profound, but you have to get used to the weirdness and decode it a bit. All of the beauty and story elements that Sean mentioned make it very attractive.
Princess Mononoke - This was my first Miyazaki film. It absolutely floored me. Such a beautiful and compelling world.
Nausicaä of the Valley of the Wind - It's got a lot of the same majestic world-building elements that Mononoke and Spirited have, but it feels a little less accessible to me. And perhaps a little more of a sci-fi feel mixed in with the fantasy.
Ponyo - This is just a great film and needs to be on both my lists.
Porco Rosso - Really strange and light hearted. Doesn't answer all your questions. Features airplanes. Tries to be Italian.
If you take one of these lists for a spin, let me know what you think. Thanks again Tim for letting me re-publish this!