That’s the question Entertainment Weekly Popwatch writer Jennifer Armstrong attempts to answer.
She comes to this conclusion in her essay: "It seems to me that the answer to his extraordinary ability to survive any scandal lies in his choice of roles. From early on, he’s leaned into his natural tendencies, almost always playing cocky screw-ups with a dark side.
"His cameo as the sexy, leather-jacket-clad criminal Jennifer Grey meets in the police station in ‘Ferris Bueller’s Day Off’ set the template for his entire career. His beloved-cad roles on television have taken no pains to hide their parallels with Sheen’s real-life persona: On ‘Spin City,’ his skirt-chasing deputy mayor was named Charlie Crawford; on ‘Two and a Half Men,’ his irresponsible, serial womanizer is named Charlie Harper.
"His antics just seem a natural extension of the guys he plays; audiences have come to expect nothing else from him, unlike Tiger Woods, who’d cultivated a saint-like image before his scandal broke."