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Dolly always made sure that Frank was well dressed and had plenty of friends and money. (Lahr 7) Even though this was in the middle of the Depression, Frank had 4 suit jackets going into high school and five cars during his teenage years. Dolly and his two uncles all agreed, "We spoiled the kid". (Handy, Time article) In the poor town of Hoboken, Frankie had everything, pocket money, nice new clothes and a car or two. Frank was the only kid walking around like is, which was very unusual seeing how it was the middle of the Depression. The other kids never had these luxuries; they had next to nothing.
Frank wanted Dolly to love, trust, appreciate him, and acknowledge him, so he would do everything for her. (Lahr 11) He would do the same with his friends, he earned the nickname "The Innkeeper" because he would "feed" them to get what he wanted and needed. Frank first realized that he could sing at his parents" barroom when one of the men put him up on the piano so he could sing along with the roll. Years later, at a lecture Frank gave at Yale University, Frank said that he once got and nickel for his "racket". (Lahr 9) He never forgot that moment. Dolly was a singer and sang in the choir and at local democratic parties, but she didn't want Frank to sing at all. Dolly didn't think that a singer was a respectable job and she didn't have any faith in it. (Lahr 9) When she saw a picture of Bing Crosby on the wall in Frank's room, she threw a shoe at him and called him a bum. Frank moved out to further his singing career away from his mother shortly after the Bing Crosby incident. Dolly realized that she could not stop him from singing and eventually pitched in for orchestrations and bought him portable speakers and a microphone. She also used her political influence to get him gigs at Democratic parties and barrooms. Frank went to see Bing Crosby in concert and that was when it really hit him, he knew that he had to be a singer.