So when I was approached by local Chicago entrepreneur and folk-rocker Al Rose about designing packaging for his upcoming album “My First Posthumous Release” I happily jumped on board. Having free creative reign on a project is always an interesting challenge. Before I could even start brainstorming, however, Al emailed me to say he loved an image I’d posted called Devil’s Own Day which was part of a continuing series of things that were a side effect of watching Ken Burns’ Civil War series too much. But with that, I had a path to pursue.

First thing, I had to find a different model. For my own obsessive reasons I couldn’t directly use my Sherman images, and I didn’t think he worked for what I wanted here anyway, so I went to my favorite source of quality Civil War imagery, Wikipedia, and poked around. Found some candidates but ultimately settled on fallen hero of Gettysburg, General John F. Reynolds. It was really the epaulets that did it.

I ran my selection by Al and he had some suggestions about the image. First he wanted to lose the cavalry saber and he didn’t like the hat. He wanted to avoid the image looking too overtly military, but happily I was able to sell him on the epaulets, too. So I went back to the internet for some hat research, and dug up a lot of shots of marching band attire on Google image search. Also via the Google, I found an image – high resolution, no less – of the exact Martin acoustic guitar Al plays. Maybe I’m too lazy, but I can’t imagine the amount of library digging and so forth finding all this source material would have required. And that is why we love the internet. So, I took all of these elements and a photo I shot of Al and quickly cobbled them together into a collage for approval.

Which approval I got. So then, I started drawing over top of the collage in Photoshop with on my tablet to try and turn it into a single image. I considered — briefly — keeping it all photographic and trying to turn it into a unified antique photo, but I didn’t think the quality of all my source material was up to snuff for that and also it wouldn’t have been the effect I really wanted. So the drawing. Unlike the “Devil’s Own Day” I used a fairly fine brush so I could do lots of hatching and build up and at simulate however faintly a period etching. It made the process quite a bit longer but I think the ultimate effect was worth it. Also, making the whole image as a drawing made things like changing the plume on the hat and making the guitar fit in much simpler.

Then: color. I kept the colors brighter than I actually wanted them in anticipation of the aging process later. Also I kept them fairly flat as they might be on an hand-colored etching.

One element was still missing, that being the sacred heart. Here I got to incorporate one small item of existing branding by taking the red spade from Al’s current web site, turning it over, roughing it up a bit, adding some assorted filigree and setting it on fire.

Late in the game I decided against using the dark, blank background used in the General Reynolds photo. I felt like it worked as background for a photo, but would make the drawing feel half-finished. So, once again the internet — in the form of Shorpy the 100-Year-Old photo blog — came to the rescue with the perfect image. With some more drawing and and some more coloring, everything came together…

...and became this. Not too military, not too Sgt. Pepper. I kind of like it. It’s good enough to let me move on to working on the frame, anyway.

The original frame I settled on came from the unstoppable iStockPhoto. But the unavoidable fact was that I still had to add text to this ornate frame which was going to lead to problems.

Like so. It’s not horrible exactly, but I could see that no amount of Photoshop massaaging was going to free the image of the unwanted sheen of fakery. So I decided on a different approach.

Mucking around with the channels on the above image I pulled out shadows, midtones and highlights and filled them in different layers with different shades taken from the original. Well, there was a little more to it than that, but that’s the basic idea. then I broke up these layers with a sketchy, streaky vertical mask to antique and grungify the image. The result is a less literal-looking object than the original stock photo, but something that I hope feels like an antique in a more authentic way.

So then the drawing required its own antique-ing: some layers of crumpling, some hue-shifting, stains and scratches. And with that, the transformation from 21st century singer/songwriter to post-bellum troubadour is complete: