Best oak tree to plant?

I don’t have either, but my next neighbors do, and based on their 25 year old trees I’d choose the Shumard (or a cherry bark red oak) over the Nutall oak. Nutall looks good, but the Shumard, IMO, looks better.

Cherry bark oak and Shumard almost look identical, but the cherry bark has a fuzzy, lighter green underside of leaf which make its stand out visually when there is sufficient breeze to rustle the leaves.

What about American Sycamore? Fast growing and stunningly beautiful against a blue sky.

I love Shumard oaks. It's my go to typically, but they can get big.

An alternative that I like is a Drake Chinese Elm.

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Do you have a big yard?

black thornless honey locust is nice, if you can find them

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Looking at the Shumard and Nuttall oaks due them being fast growing and like the heat. Mainly looking to provide shade and pretty fall foliage.

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Shumard oak is prettier foliage and some color in the fall but since both are red oaks, you need to consider where they will be planted. If it's a low area and could possibly hold a little water, The Nutall will do better. If it's in a raised type area, the Shumard will do better.

My parents bought a "Mexican Oak" a few years ago and DAMNNNNNN, that thing grows super fast. Pretty tree!

In terms of oaks, I would go with Nutall or Shumard as previously stated. The Nutall will give you a mix of red/orange fall color depending on the fall season.
Shumard will give you a scarlet red to orange fall color.

They both grow a bit slower than the white oak family.

The Chinese Pistache he would near the top of my fall foliage list.

The sugar maple would probably be at the top for its brilliant vivid orange/yellow fall color.

However depending on where you are located a different Acer variety may do better such as Florida Flame or Autumn Blaze.

Another good hardwood to consider would be the regular hickory or shagbark hickory.