All of the paintings in this post were ones my Dad did of me at various times in my life.
The one above is a charcoal drawing but I'm including it because it's my favorite of my dad's portraits of me, although its not a painting. The last painting is perhaps the one I find the most interesting of his paintings of me. The next to the last was done when I was around 20 and is the oldest I was when he painted me.
What I really wish I had to show my Dad as a joker was a sketch he ended up giving someone else.
When he was in the hospital, near the end of his life, he had a urinal version of a bed pan. He put a flower in it and did a good sketch of the flower in the urinal. He treated it seriously as a flower drawing and looking at it you'd do a double take on realizing the flower was in a urinal. If he'd painted it instead of drawing it, and if I had the painting it would have been perfect for the theme.