Old Woman Josie, out near the The Car Lot, is a citizen living on the edge of town next to You and Your trailer and also near Larry Leroy. She calls into the station often to tell Cecil what she knows, and also frequently voices her opinions at City Council meetings.
Her home is the informal shelter for local angels, who help her with various household chores and protect her from things such as the Creeping Fear. The black one helped change her porch light. She seems to be the first person in Night Vale the angels revealed themselves to. As a result, her house is always surrounded by a halo of bright heavenly light.
Old Woman Josie is typically friendly and helpful. She used to bowl in a league with Cecil, and she often calls him at the radio station to report on goings-on she sees around Night Vale, things happening with the angels in her home, and more.
Old Woman Josie seems to know a lot about most people in town, but she is directly stated as having personal relationships with these people:
Cecil Palmer: It is mentioned that the two used to bowl on a team together in a league. They seem to speak to each other like good friends, though it's clear they haven't been keeping up with their friendship, and she calls into the station often to tell Cecil everything she knows or to comment on the goings-on around town.
The Angels: After the Angels reveal themselves to her, they often operate as indirect informants for Cecil through their gossip with Josie. She has opened her home to them, and they often accompany her on errands and around town, telling her things they know, ranging from baseball plays to what's in the deerskin suitcase. Though they seem to occasionally get on her nerves - standing in front of her TV, for instance - it seems they have a desire to protect her, even after they disappear from her home.
When the angels left in Yellow Helicopters, she feared she had bored them, but they came back to protect her. She also brought corn muffins to the town meeting in Pilot, though they lacked salt because the Angels needed her salt for a heavenly mission.
In the City Council meeting that occured in the episode PTA Meeting, Josie agrees with the measure to remove the large, lead-plated door from Radon Canyon, adding that lead is a health hazard. In the same episode, Cecil is told by Josie that Carlos "was still absolutely perfect, and smelled of lavender chewing gum."
She is with one of her angel friends at the gas station when the angel claims to recognize Rita Hayworth, who Josie says was looking "a bit older, moderately obese, and considerably more Hispanic", though the angel insists it is Rita Hayworth.
In the episode History Week, Old Woman Josie digs up a box from a corner of her yard, carries it delicately cradled in her arms, and buries it in another part of her yard.
In The Man in the Tan Jacket, she calls in to say that her angel friends have informed her that TMITTJ's deerskin suitcase is full of flies. The angels would not tell her more, as doing so would jeopardize her Eternal Soul. She suspects that he's just an annoying fly salesman. However, an angel purportedly calls the station minutes later, claiming that The Man in the Tan Jacket is from a place "underneath the Earth", then whispers "A flower in the desert," probably indicating the Desert Flower Bowling Alley and Arcade Fun Complex.
In The Sandstorm (Part A), it is noted that Josie did not call in, but that Dana reported that Josie had updated her Facebook with an Instagram of some rune stones, which Dana translates to a warning about the sandstorm doubles: "They come in twos. You come in twos. You and you. Kill your double!"
In Poetry Week, she calls in to tell Cecil that the poem signed "E" is from one of the angels, and that all angels are named Erika, with a "k". In The Mayor, she calls in to say that she has seen Mayor Pamela Winchell in a heated conversation with the Apache Tracker, who then opened a leather briefcase full of flies. In Yellow Helicopters, she reveals that the angels have been gone for three straight weeks, and later calls in to say that a half dozen yellow helicopters are circling her home, and she is not seeing any sunlight despite her clocks telling her it is the middle of the day. She assumes it is the angels efforts to protect her. The helicopters have a large triangular logo with an orange "S". After a discussion with Cecil about their old bowling league, she tells him the sunlight has come back, ending her protection, and the line goes silent.
The next mention of Old Woman Josie is in A Story About Them, and it is only long enough to say that her house has been "silent and empty for months now".
In Parade Day Claire Wallace, a freelance photographer, sent in photos of a door that appeared in the empty lot across from the Rec Center. In these photos there's an old woman who's face can't be seen, but it can be assumed that this is Josie. In the first picture she's putting up a sign that reads “Future home of the Old Night Vale Opera House” with “Josephina Contracters, Inc.” in small print across the bottom of the sign. She's returning to the door in the next picture.
Josie was the chairwoman of the Night Vale Opera for many years until it folded in the early 90s when a massive puppy infestation destroyed the theater's infrastucture. She also used to be on the same bowling team as Cecil, but the two have spent less time together lately, possibly due to the discovery of the miniature civilization beneath the Desert Flower Bowling Alley and Arcade Fun Complex and Cecil having a new boyfriend.
Old Woman Josie seems to have a counterpart in Desert Bluffs by the name of Grandma Josephine.