Ryan Phillipe
Ryan Phillipe, who co-starred in the 1999 film Cruel Intentions opposite Reese Witherspoon, rose to popularity as a result of his performance. The two started dating while working together, went on to get married, and now they have two children! Although they tried to make their relationship work, it was ultimately unsuccessful, Phillipe has proceeded to carve out a great career in the entertainment industry.
Ryan Phillipe
He has barely altered in the 22 years since Cruel Intentions! Since then, Phillipe has appeared in the thriller series Shooter, the neo-Western crime drama The Way of the Gun, and the Oscar-nominated black comedy Gosford Park.
Jason Biggs
During the late 1990s, the American Pie series came to symbolically represent a whole generation of adolescents. These silly movies with X ratings were a commercial success, and they helped Jason Biggs get his acting career off the ground. Even though he has appeared in Orange Is the New Black and has a number of other credits to his name, he will forever be known for his role in American Pie.
Jason Biggs
Biggs still has the same appearance as when the first movie came out, 22 years ago! Fun fact: He plays cowbell in the band Yukon Cornelius and writes literature as well.
