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As a part of "old Hollywood," Shirley was often around legends like Frank Sinatra, Dean Martin and Sammy Davis Jr.—part of the infamous Rat Pack.
"The brilliance of old Hollywood, particularly with the live performers, ... [is] they always told the truth about everything," Shirley says. "[There was] authenticity about their lives. About what they were afraid of. For example, Dean and Frank would be [onstage] and Frank would tell a joke—but nobody would laugh. Then Frank would throw it to Dean and say, 'You tell the joke.' Everybody would convulse. Frank would say, 'Why didn't they laugh at me?' And Dean would say, 'You're just not funny, Frank.'"
"When you were in it with Frank Sinatra and Dean and Sammy Davis Jr., ... did you know then what it was?" Oprah asks. "Did you know that it held the level of glamour and Hollywood-ism that it now holds?"
"No," Shirley answers. "I didn't know who they were."