The first painting Dean made got him sent to the principal's office. The first painting Sam made won him an award and made his entire class crowd around it. It was Sam's idea to go to the dollar store and get the cheapest acrylic paints one could buy, and show Dean how to create art that didn't make assistant principals faint. Sure, Dean grumbled, and asked what the hell kind of a name 'chartreuse' was for a color, but once Sam sat him down in front of a tree by the motel parking lot and handed him a 50 cent brush, he began to peer at the subject of his art. Slowly dipping the bristles into a blotch of slimy brown paint, Dean began to sketch out the long, outstretched tree limbs.
"You've got talent, I know it," Sam had said, and Dean glanced over at the eight year-old's hopeful smile, encouraging him to continue. The twelve year-old's brush strokes were surprisingly graceful, and Sam 'ooh'ed and 'aah'ed throughout the whole process. A few times Dean got impatient and almost ruined the painting with angry strokes, but Sam stopped him every time. And at the end, as the sun was setting and casting fantastic shadows, the brothers gazed at the most beautiful painting Sam swore he'd ever seen.
"You think so?" Dean breathed, green paint on his callousing hands and a bright look of appreciation in his eyes. Sam nodded then, looking more serious than an eight year-old should ever look.
He blinked at his older brother and told him gravely, "Dean, promise me you won't ever think you're bad at something. Okay?" And though he believed it at the time, Dean Winchester had no idea that his 'okay' would be meaningless for a long time.