All of you have some great thoughts about That Painting.
My own take is on Paulie having Tony's image remade into a Napoleonic figure. IMO it was a very interesting choice.
History buffs may recall that the real Napoleon, blinded by ego and earlier successes, campaigned against Russia to add it to his growing Empire. He lost, retreating in abject failure as his Grand Armee was decimated by the fierce Russian winter. He escaped from banishment to Elba; lost his bid to regain power against united European armies at Waterloo; and died in exile on St. Helena, an isolated island off the southern African coast. (For a brief but more detailed look at Napoleon's career click here
One wonders if the image of Tony as Napoleon mirrors his own career and destiny as a mob boss.