Assuming you mean breaking into systems, while I'm not immersed in that culture, I did enjoy Kevin Mitnik's Ghost in the Wires. It may be a bit dated, but some of the stories of early phone phreaking and social engineering was a fun ride -- and helps add a decent level of paranoia to answering phone calls today! Kevin Mitnik is a legend. He might not be the best of all time or today, but he is up there.