Ryan Phillipe – Then

Ryan Phillipe emerged as a quintessential bad boy in the early 2000s, quickly capturing the hearts of many. His breakout roles in films like Cruel Intentions and Crash showcased his talent for playing complex characters that often walked the line between charming and rebellious. His performances earned him a reputation as a heartthrob, appealing to audiences who were drawn to his intense on-screen presence.

Shutterstock // Matt Baron

Beyond his acting prowess, Phillipe made headlines for his personal life, notably his marriage to co-star Reese Witherspoon. This high-profile relationship further elevated his status in Hollywood and among fans. Throughout the decade, he continued to take on challenging roles, displaying versatility and depth in his craft. As he navigated the ups and downs of fame, Ryan Phillipe solidified his place as one of the notable actors of his generation, gaining a loyal following who admired both his talent and charisma.

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