Jimmy Shive-Overly

Jimmy Shive-Overly is a British novelist in Los Angeles, coasting on one early success and convinced of his own brilliance. He crashes a wedding to steal cake, insults everyone in reach, and picks up Gretchen with the confidence of a man who has never once doubted his own charm.

Chris Geere plays pomposity as a survival strategy rather than a punchline, so the put-downs land funny before you notice how much armor they're doing. The show trusts Jimmy's awfulness completely, refusing to soften him for likability, which is precisely what lets flickers of real feeling underneath hit so hard.