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White Mentor. Because of his family's straitened circumstances, the authorities placed Flip in foster homes. He went from a strict Catholic family to a fortune teller to a family that was almost fanatically pentecostal. In desperation, he kept running away from his foster homes (13 times in all) and was finally sent to reform school. Life there was downright Sybaritic compared with his life on the outside. To ensure that he stayed in, he made a number of escape attempts, which he knew would be "punished" by extensions of his term. "My happiest memory of childhood was my first birthday in the reform school," he says. "My teacher gave me a little package. It contained a box of Cracker Jacks and a can of A.B.C. Shoe Polish."
When he was 13, Flip rejoined his father. After sporadically attending public school, he dropped out and picked up odd jobs on construction sites, in bowling alleys and at parking lots. Then at 16 he lied about his age and joined the Air Force. "I wasn't patriotic," he explains, "just tired of being ashamed of my clothes. And the Air Force beat parking cars for a living." He was assigned, like many other blacks, to kitchen duties. There his cheerfulness and intelligence impressed a white Southern major who gloried in the name of Lloyd Llewllyn Lancaster Lynn. Major Lynn became the first of several white mentors who have guided Flip's life, persuading him to go back to school to learn typing and grammar. Meanwhile, Flip was earning a reputation—and his nickname—by "flipping out" people with his stories and clowning.
In 1954, at the age of 20, Flip left the service and became a $40-a-week bellhop in a San Francisco hotel. He got his first break in show business when an adagio dance trio, the hotel's floor show, let him fill in with a drunk routine while they changed costumes. When the three went off to their next date in Stockton, Calif., Flip went with them—at $1 a night. Soon he left them and started a seven-year odyssey across the country, working the small Negro clubs and sleeping in cheap hotels, bus stations, pay toilets and even on the tops of parked cars. "Those black audiences in the little weekend clubs were the toughest I've ever played for," he says. "With all the trouble black people have, they try to forget on weekends. You've got to be good to make them laugh."
While Flip was playing a small Miami club in 1956, another mentor appeared in Herbie Shul, a local white businessman. Shul saw enough promise in Flip to become his angel for a year, giving him $50 a week while Flip worked engagements in Florida and the Bahamas. The following year Flip married—and almost immediately divorced—a dancer he met in Nassau named Peaches. His feelings about the episode are indicated by the fact that he will not reveal Peaches' last name. In any case, he did not repeat the experiment in matrimony until 1961 in Miami, when he took his second wife, Blondell, by whom he has since had four children.