Jackson attracted the attention of the William Morris Agency, a firm that promoted her by booking her in large concert halls and television appearances with Arthur Godfrey, Dinah Shore, Bing Crosby, and Perry Como in the 1950s. Her reverence and upbeat, positive demeanor made her desirable to progressive producers and hosts eager to feature a black person on television. She appeared at the 1956 Democratic National Convention, silencing a rowdy hall of attendees with "I See God". Miller, who was in attendance, was awed by it, noting "there wasn't a dry eye in the house when she got through". Jackson broke into films playing a missionary in "St. Louis Blues" (1958), and a funeral singer in "Imitation of Life" (1959). As demand for her rose, she traveled extensively, performing 200 dates a year for ten years. She and her entourage of singers and accompanists toured deeper into the South, encountering difficulty finding safe, clean places to sleep, eat, and buy gas due to Jim Crow laws. Sometimes they had to sleep in Jackson's car, a Cadillac she had purchased to make long trips more comfortable. Jackson remembered, "The looks of anger at the sight of us colored folks sitting in a nice car were frightening to see... It got so we were living on bags of fresh fruit during the day and driving half the night, and I was so exhausted by the time I was supposed to sing, I was almost dizzy." Jackson began to gain weight. She also developed peculiar habits regarding money. As a black woman, Jackson found it often impossible to cash checks when away from Chicago. Her contracts therefore demanded she be paid in cash, often forcing her to carry tens of thousands of dollars in suitcases and in her undergarments.