A self-styled cultural outlaw and motorcycle customizer-turned-basic cable celebrity, Jesse James rose to notoriety as the host of a popular reality series, only to earn the scorn of millions in the aftermath of an exceedingly tawdry extra-marital affair. After James' celebrated custom motorcycle shop West Coast Choppers became the backdrop for the series "Monster Garage" (The Discovery Channel, 2002-06), the heavily tattooed mechanic moved from niche notable to mainstream media personality, particularly after appearing as a contestant on "The Celebrity Apprentice" (NBC, 2004- ). Popular as he may have become, many were nonetheless left scratching their heads at the news of James' marriage to "America's Sweetheart," actress Sandra Bullock in 2005. As both of their careers reached respective new heights near the end of the decade, earlier concerns about James' fidelity were borne out when several women publicly claimed to have had affairs with the married man. Figuring most prominently in the rumor mill was tattoo artist and model Kat Von D, with whom James became briefly engaged to in the year after his divorce from Bullock. In hindsight, the title of his brief daredevil reality series "Jesse James is a Dead Man" (Spike, 2009), may have been oddly prophetic, as James pondered his future in the wake of the humiliating Bullock debacle.