10 Celebrity Pairs You Won't Believe Went To School Together

8. Charlie Sheen & Robert Downey Junior In what probably has to go down as an all time "humanity was robbed" moment, it turns out that the two biggest American boozers and floozers of the late twentieth century attended high school together but did not party together. Charlie Sheen and Robert Downey Junior attended Santa Monica High School along with Rob Lowe and Sean Penn, in the beginnings of what was later to be called the Hollywood Brat Pack. While Lowe and Penn graduated, Sheen and Downey were the ubiquitous beauty school drop outs, preferring instead to follow movie careers, improv and substance abuse. Downey was subsequently nominated for an Oscar for playing Charlie Chaplin but soon hit the skids and was arrested in 1996 for possession of cocaine, heroin and an unloaded .357 magnum while speeding down Hollywood Boulevard. Charlie Sheen had a successful film career that included Platoon and Wall Street and a television stint on Two And A Half Men that derailed spectacular when issues with drugs (and some say untreated manic depression) caused him to famously implode. While RDJ has cleaned up his act and become king of the box office playing Iron Man in four films with more to come, Mr. Sheen has become King of Delusionville. History still needs to know how close they came to a real life Weekend At Bernies, as had these two ever joined forces, we would still be talking about it.

Contributor
Contributor

I am a d-list straight to video actress who owns a used bookstore. I was a house writer for the Canadian film magazine Home Movies and have also contributed to the U.S. publication Super Eight today. I won a Saskatchewan Writers Guild Award for my short story My Dream Date with Roger Ebert. I am also a contributor to Cracked. com.