#10: Heather Hunter, The Beginning
His Age: 26
Their paths crossed in the early 1990s through Hollywood’s after-hours ecosystem, where fame, curiosity, and provocation overlapped freely. Heather Hunter was already notorious, unapologetic, and visible. Charlie, emboldened by success, was increasingly drawn to people who existed outside conventional Hollywood respectability.
This connection formed during a phase when limits felt optional. Charlie’s career was thriving, his image rebellious rather than reckless—at least publicly. The relationship began less as a courtship and more as an extension of lifestyle, driven by fascination, bravado, and the confidence of someone who hadn’t yet hit resistance.