Justin Timberlake's recent arrest for alleged driving while intoxicated led to a surge of memes and jokes on social media, marking a stark fall from his two-decade reign as a pop superstar. The incident highlighted a shift in public perception, with concerns about his treatment of women casting a shadow on his once pristine image. Timberlake's past controversies, including the infamous "Nipplegate" incident with Janet Jackson and his relationship with Britney Spears, have been reexamined in light of recent revelations. Despite attempts at redemption, such as issuing apologies and releasing new music, Timberlake's latest album received a lukewarm response. His declining popularity has been attributed to a disconnect from the current pop music scene and a failure to live up to past successes. To rebuild his reputation, Timberlake must address public concerns openly and honestly.