There are no painting simulations; there are only programs that let you actually paint and, with the exception of kids' stuff, only one offering I know of that has managed to harness the creativity needed to paint into a game. Said game comes with the truly apt and descriptive title of 90 Second Portraits and, rather impressively, it is also a winner of Ludum Dare 31 -- the very last Ludum Dare of 2014.
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Here's how it works. You are cast as an artist who has to pay the bills by speed painting portraits of bypassing customers in 90 seconds. You'll try to capture the essence of their visage, complete with background and everything, using only a couple of brushes, a bucket and a palette that holds four (mixable) colors. You'll get graded and appropriately paid for each portrait you make and your day will ends after 5 customers.
Yes, it is this simple, but it is also innovative and you'll get to grips with it intuitively.
The mixing tools are excellent, the drawing tools highly effective and the game even does a pretty decent job of understanding how closely you captured each of your clients characteristics. 90 Second Portraits is an awesome and spectacularly silly idea brilliantly implemented. A masterfully realized strong vision, where everything fits together. The art, the mechanics, the funny little sounds, the music and the menagerie of vampires, aliens, gnomes and regular people of all shapes you'll get to paint make for a nigh unmissable little polished game you cannot afford to ignore.
And though 90 Second Portraits will indeed turn you into a better artist, what with it forcing you to focus on general shapes and the basics of composition, here are a few tips to get you going: The background is your first priority. A couple of buckets of hastily mixed colour and a few strokes should generally be enough before moving on to the head and a rough outline of the customer's body. Oh, and do save a few seconds for little touches such as the eyes or some rudimentary shading here and there.
Of course, your first creations might be on the ridiculous side of things, but that's okay. This is supposed to be a humorous game after all and even Kandinsky was a child once. Besides, you'll soon get better and maybe even feel the need to share your creations in places such as, say, the RPS comments section.