The song "Jessie" by Joshua Kadison tells the story of a woman named Jessie who reaches out to the singer from a phone booth in Las Vegas at 5 a.m. She expresses her dissatisfaction with her current life and tells him about her dream of living in a trailer by the sea in Mexico. Jessie suggests that they drink tequila and search for seashells, portraying this as a sweet and appealing lifestyle. Despite being aware of Jessie's tendency to sell dreams and make promises that often don't come true, the singer is still captivated by her charm and continues to fall for her illusions. He acknowledges that her dreams are never free and that he should know better, but he still allows himself to be drawn in. The singer reveals that Jessie's absence has affected a cat named Moses, indicating that Jessie holds a significant place in their lives. They removed her pictures from the wall, but she knows when to call and when to bring them back together. Jessie convinces the singer to gather his belongings, bring Moses, and embark on a new adventure, promising that this time it will be different and last. The lyrics convey the singer's yearning for a romantic relationship with Jessie and his willingness to believe in her dreams, even though he knows they may not come true. He pictures a life with her filled with love, warmth, and happiness, hoping that this time things will align with Jessie's plans. Overall, the song "Jessie" portrays a complex relationship dynamic where the singer is both drawn to Jessie's enticing illusions and aware of their transient nature. It highlights the power of dreams and the emotional vulnerability we may experience when falling for someone who can sell us any dream.
