#17: Reese Witherspoon and Ryan Phillippe
They were the ultimate ’90s movie couple, starring together in the drama Cruel Intentions (1999). Reese Witherspoon and Ryan Phillippe’s youth, good looks, and on-screen chemistry made them an iconic pair of that era. When they married and had two kids who looked just like them, it felt perfect. Their divorce felt like the true end of a chapter for many who grew up with their films.

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