Penn, Robert Downey Jr., Charlie Sheen, Rob Lowe
We don’t even have to stop at those four famous actors, by the way, since Charlie’s brother Emilio Estevez also went to school with Penn, Downey, and Lowe. It’s hard to fathom a more star studded graduating class than this group that attended Santa Monica High. According to Lowe, Charlie Sheen would actually wear bullet proof vests to school because he was utterly convinced gang members were gunning for him. Despite Sheen clearly being fairly insane even back then, the group was tightly knit through high school, and would obviously go on to be some of the most famous names in Hollywood. Well, aside from Emilio, anyway. When your most memorable role is as a pee-wee hockey coach, you can’t really claim a whole lot of fame.
Anderson Cooper and Christian Slater
Anderson Cooper is one of those guys whose age has always been hard to peg because the dude has just seemingly always had white hair. You know, kind of like Steve Martin. However, if you want to get a general idea of how old the CNN host actually is, here’s a hint: he went to high school with Christian Slater, better known as the former teen heart-throb who so desperately wanted to be the next Jack Nicholson. The pair both attended the Dalton School in New York, which is about as ritzy as you probably guessed based on that name. After all, an important thing to remember about Cooper and where he comes from: he’s a freaking Vanderbilt. So, yeah, he comes from a little bit of money.
Lauryn Hill and Zach Braff
Lauryn Hill has kind of dropped off the map these days, in part because she seemingly went a little crazy, but there was a time when she was the absolute biggest female star in the entire music industry. And as it turns out, she went to high school and was good friends with Zach Braff, the nerdy, goofy star of Scrubs and Garden State. Hill kind of made a name for herself as being kind of militant about her heritage, but according to an interview Braff did with Howard Stern, she was nothing like that when they were growing up. Obviously, people and their views can change, but from Braff’s description it sounds like she was more like one of the Cosby kids than the hardcore rapper and singer she would grow into.
Stan Lee and "Sugar" Ray Robinson
If you were walking around the halls of DeWitt Clinton High School in New York in the late 1930’s, you’d stand a solid chance of bumping into one of the most famous boxers of all-time, and then a moment later, the most legendary comic book writer in history. “Sugar” Ray Robinson and Stan “The Man” Lee both went to DeWitt, and while we have absolutely no reason to believe they were actually pals, isn’t it nice to imagine that the original Sugar Ray was besties with the guy who created Spider-Man? Oh, and another fun note about DeWitt: not only the creator of Spider-Man and, well, pretty much the entire roster of Marvel heroes graduate, but so did Bob Kane and Bill Finger. Or, if those names don’t mean anything to you, the two guys who created freaking Batman.
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