In this illustration, photographs were used for some of the elements. Open the photograph you wish to use in Photoshop and using the Lasso tool, isolate the desired areas. Once selected, Copy > Paste into the main image and repeat with any other areas. In the photograph used here, the back of the hat was cut away with a slight ‘halo’ so as to make it appear under the wing and behind the head using the Eraser tool.
Next, add colour to the image. Create the stars simply using the Polygon tool and setting the Geometry Options to Star. Draw the Soviet hammer and sickle on the star with the Brush tool and add a rough edge to the star with a textured Eraser brush. Copy > Paste the finished star to create multiple stars; resize each star using Edit > Transform > Scale and then use the Move tool to position them so they appear to be coming out of the character’s mouth. Finally Layers > Merge Layers to get all the stars onto one layer.
Draw Cuba flat, using a Brush tool on a new layer and distort it using Edit > Transform > Distort. This tool allows you to manipulate a 2D layer almost as if it was in a 3D space. Drag any one of the eight points to change the shape; in this case the top two are pulled in and dragged across to make the top of the drawing appear to move into the background.