Tony Soprano's sharp tongue often cuts as deep as his actions, with lines like telling his son A.J., "I'm supposed to get a vasectomy when this is my male heir. Look at him," showcasing his brutal ability to demoralize even his own family. But it’s his calculated digs at his sister Janice—mocking her abandoned son to shatter her newfound happiness—that underline just how much pain Tony revels in inflicting. Let’s dissect these and other chilling moments from the man behind The Sopranos—watch the video to explore them all!