>>515972441
>>515969524

Here we go, earliest one I can find is The Temptation of Christ by the Devil in SanBaudelio de Berlanga from the 12th century

It's faded because the painting being a mural but the demon on the most right corner still shows clearly

there are lots more from the 13th century because of better preservation and the Alhambra decree, that expelled most of them, was on that century, even after converting they still managed to piss off people