Until the creation of the new Hollis/Brookline High School in 1997, the middle school building served as the high school for both towns, with grades seven and eight occupying the current Hollis Upper Elementary School.
It is home to the Northeastern University baseball, men's soccer and lacrosse, and women's soccer teams as well as the Brookline High School Warriors football team.
All the interior and exterior high school scenes were filmed on the Brookline High School campus, except for the scene in the gymnasium.
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Growing up in Brookline, he went to Brookline High School, where he took trumpet lessons and was exposed to rap by a friend of from the projects.