Hello!
I mean not a duel with big canvases. I'm just reading a book about the 16th Century.
Year 1541: Michelangelo works on a fresco, The Last Judgement. (Rome)
Biagio de Cesena (a functionary in the Vatican) is highly indignant at so much nudity on the wall. Michelangelo took a terrible revenge: Cesena's face is on the figure at the far right and bottom on the fresco, as Minos, Judge of the Underworld! See what the snake make with him.
Wow, revenge with a built-in longtime effect. He was a sensitive man.
Today: Imagine, at night, armed with a few big jars of paint and a 500 W reflector on jeep (or family can help to hold this). The housewall of your disliked ex-teacher. You paint a very ugly portrait of his style: a little Dali mixed with more Picasso. (Of course alla prima,you have only one night.)
Next day: You get a check for about $5,000!
What went wrong? 1. You've signed it! 2. He is a teacher for modern art. His favorites are Picasso and Dali!
Best wishes!