Ah, City of Angels. I thought I was getting cool film noir but got a cheesy musical instead (Google it if you must). Still, it was fun to make the poster and associated images, mostly because the research consisted of watching real films noir and buying a great book on movie posters of the genre. I made tons of sketches and a few digital mock-ups.
For the final poster above, I made three separate watercolour paintings (one of the couple and one each of the two black and white heads) and composited them in Photoshop, where I also added the text. In true movie poster fashion, I wanted the actors names to be the top two names, but I lost that battle and had to use the characters' names instead. It looks fine, but it implies that "Kingsley and Stone" are the lead actors in the show. Oh, well...it's only community theatre...
By making the "angel" above half black and white and half colour, this mock-up is supposed to evoke the b&w ("movie" characters) vs colour ("real life" characters) concept of the show and is executed in a bit of a contemporary, rather than period, style. If this version was chosen, the final poster would have been painted, using a cast member for reference and not the model above.
This mock-up is a photo collage of some of the actual cast members. I shot them during a rehearsal, hence the sports jersey on the detective. The more I look at this, the more I like it better than the final poster because of the more interesting composition and the black-white-red colour combo looks bold and somewhat mysterious.
I also designed t-shirts with two front variations. These weren't based on cast members but friends I had pose specifically for the shirts.
The femme fatale:
...the hard-boiled detective:
...and the back of the shirt, which was identical for both front versions: