I started with a collection of various aircraft photos I had taken. I began to build layers in Photoshop, isolating the objects I wanted to use.

I put the planes in the sky outside the cockpit of a B-17 bomber I photographed while on a tour of the aircraft in Colorado.

Of course I needed a sky and a poster background.

How about a few more planes out there and a desaturated blowup of the cockpit to blend over the background. 

I added a title using a rusty metal font, a movie tagline in sans-serif, and some credits using the SFHollywood font.

This is my oldest in his flyboy stocking cap. I matched color and added shadows to place him in the scene.