Ryan Phillippe was at one time one of the hottest young stars in show business and his star was rising quickly when what seems to happen to a lot of stars decided to up and happen to him, he became less than relevant for one reason or another. There are a number of reasons why this happens but there’s no one definitive reason that it can happen to anyone since some folks just rise too quickly and burn out and some tend to become disillusioned and tired of the business and need to step away for a while. With Ryan it almost seems like he was still trying to reach higher and higher when suddenly a new batch of stars came in and somehow supplanted him without anyone being the wiser until it was too late. But thankfully as he’s gotten older he’s started taking on other roles that have treated him well, such as the televised version of Shooter.
Here are a few of his best movies from when he was still rising swiftly through the ranks.
5. I Know What You Did Last Summer
You could almost predict when each person in this movie was going to die, but that was part of the joy since it didn’t complicate things as much, all but tagging each person before their designated death scene. As the bully and the cool rich kid that didn’t give a damn about anyone or anything other than himself, Barry was one of the most expendable characters in this movie since he declined to have much, if any, real attachment with anyone for his own reasons. He had just as much to lose before the accident that kind of ruined the group of friends in this movie, but he was also standing closer to the danger zone than anyone since he was the biggest jerk.
4. The Lincoln Lawyer
You’ve got to give him credit for this one since he did manage to act pretty innocent for a while until the pieces started coming up missing and the idea that he wasn’t quite so innocent started to appear. The one thing that any character in life or in the movies should learn however is that if a person knows a biker gang and is on good terms with them, so long as payments are made and a good defense is given, it’s probably not a good idea to mess with them. Plus, it’s never a good idea to threaten a person’s family under any circumstances, but once again, with a biker gang in his pocket, don’t challenge a lawyer when he’s been pushed to the edge.
In a big way you kind of want to feel bad for this young cop since he works with a very racist commanding officer and he’s simply trying to learn how to do his job and navigate the streets since he’s still pretty new to the force. But when he simply goes along with the idea of his CO feeling up a woman while on a routine stop in a racially-charged manner it kind of eliminates some of the sympathy. But then again it might be regained once he allows her husband, who struggles throughout the movie with the idea of his wife losing respect for him, to go after acting like a threat to a group of cops. Of course, before the movie’s over he loses any semblance of respect since he does shoot a young black man thinking that he was reaching for a gun, when in truth he was reaching for a small statuette, similar to the one the cop had on his dash at the time. In other words, he’s a green behind the ears rookie that’s way too impulsive and has a lot to learn.
Club 54 was a wild place where the rich and famous got to play and the scene was generally one of the most crazy and out of control scenes that anyone could imagine. It was like a personal paradise that was run in a manner that might never be seen again since once it was over and done with everyone within a certain radius decided to start taking a page from the playbook in order to up their numbers and attract the most famous faces and names in show business. The problem with being on the cutting edge is one way or another you eventually find yourself on the cutting room floor or being cut out of the picture completely.
1. Cruel Intentions
Sebastian and Kathryn are horrible people, that’s a well-established part of this movie that is introduced from the beginning. But there is a spark of hope for Sebastian since he does have a redeeming quality or two about him that is brought out by Annette as he tries to bed her but finds that he actually has feelings for her after a while. That being said though it’s still an uphill battle since he can’t help but being who he is for most of the movie, a rich, spoiled individual that’s used to getting his way.
He has played a few different roles in his career, and he’s done great with each of them.