Jessie is the local stud that Roger's persona of Julia falls for when he starts a new life after getting his feelings hurt by Stan in "Julia Rogerts".
Julia tells him of being hurt by a man previously as Jessie pledges vengeance. They have a date at a fair, but when Stan later reveals himself at Julia's home, Roger tries to turn to Jessie and the town for aid, finds he is to be the victim of a virgin sacrifice. Stan manages to save them and they take refuge in Roger's dried flower shop. Roger produces a bottle of wine made from the vine they had planted that was intended as a replacement for Francine's wine that Stan drank in a Roger-encouraged drunken stupor. As they try to drink Roger's concoction, he reveals that he had to bulk it out with gasoline and nitroglycerine. They flee the crowd breaking into the shop through an underground tunnel to a fudge shop across the street, where they trigger an explosion, wiping out Jessie and the townsfolk.
Jessie is voiced by Dermot Mulroney.