When given a typography based brief I looked at the work of Oliver Barret, I like the style of his illustration I think it looks hand drawn with hints of using digital enhancements to improve the colour of the images, he also adds other small images to the larger picture to give them a different feel, in the case of the Steve Jobs image he has added illustrations of some of the products he has created, they are very subtle, they do not take away from the main image itself, but they do make you have a closer look.
With typography it seems to be quite boldly just layered over the top of his illustrations sometimes almost obscuring the image below. I think these look very interesting and again make you look a little harder at the image, which really is what any artist whats you to do with their work.