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import random, glob
path = random.choice(glob.glob('~/app/static/img/funny/*.*'))
Now in the path variable you’ll have a path of a random file from img/funny
You might want to do the following if you want the path to be relative to ~/app/static/
path = path.replace("~/app/static/","")
And then you can use it in your templates like:
<img src="{{ path }}"/>
Source:stackexchange.com