First I start out with filling as many pages as I can with all kinds of ideas. I keep the drawings small and loose. Concentrating mainly on composition and shapes.
ROUGH SKETCH
After I find something that I think works, I take it and do a larger rough. Still keeping it loose and not getting concerned with detail. I'm just trying to hone in the shapes and perspective while exploring some tone too.CLEANER ROUGH
Now I'm starting to define the piece more. Tightening up the shapes and getting more concerned with lines rather than tone. Still keeping it loose and full of energy, but refining the shapes and design. Each step is an evolution towards a better image. You lose things that didn't work and define those that do. You can see I didn't like the man's silhouette and I made an adjustment to hopefully improve it.CLEAN UP SKETCH
Here's where I begin to think about detail and start to tighten things up for the final image. If I make any mistakes, I don't sweat it because I know I can make changes in Photoshop when I begin to do the tone.FINAL TONE
Then I scan in my sketch and begin to paint in the tone in Photoshop using my Cintiq. This is a huge step and unfortunately I don't really have any 'in progress' versions of this. So you'll just have to do with the final. You'll notice I never stop evolving my piece, even at the very end. Take note on the sign. I wasn't buying the "Noir" sign and I decided to change it to a more appropriate 'hotel' sign instead.
It took me a weekend to put it together and I had a blast with it. Hopefully you dug seeing the different steps!