Vincent Gray (episodes 1-51 & 100-138), played by Dan Futterman: Amy's gifted younger brother, with whom she has always been closest. Vincent is the winner of a Pushcart Prize for a collection of short stories titled "A Fortunate Son". Shortly at the beginning of the series, he becomes room-mates with Donna, with whom later he becomes best friends. As he attempts to continue his writing career, he holds a number of different jobs: dogwasher, reporter, and free-lancer. He eventually marries his girlfriend, Carole Tobey (Sara Mornell), who has breast cancer, and leaves with her for San Francisco, parting with Amy on very bad terms. Some time later, his cousin Kyle arranges for him to arrive as a surprise to Amy's wedding to Stuart Collins. The wedding never happens, but he patches things up with Amy. He returns home soon after, explaining that Carole has left him for her oncologist. He later explains that this was a lie, and that he left his wife because he could not handle the struggle of taking care of her. Still stuck on his new book, he gets a new job as a social worker.