The Sopranos: 10 Funniest Paulie Moments
3. The Horse Painting (All Due Respect. Season 5, Episode 13)
Paulie and the horse painting debacle was a joke that began in season four. After the death of Tony's beloved horse Pie-O-My and the subsequent reactionary murder of Ralphie, a distraught Tony orders that the painting be destroyed immediately.
But Paulie has other ideas and rather than destroy the portrait, he decides to take the painting home and hang it on his living room wall. A curious decision made even more bizarre by Paulie opting to modify the painting by transforming Tony's outfit into a Napoleon-style attire!
The horse painting story came to a conclusion in the finale episode of season 5, when Tony makes an unexpected rare visit to Paulie's house. As soon as Paulie opened the door, he knew that a confrontation was inevitable.
Paulie tries to explain his decision as an appreciation of art and an illustration of his loyalty. Tony isn't buying Paulie's explanation and so he promptly takes down the painting, before then throwing it into the garbage. Not Paulie's finest moment, but it could always be worse...