"He's the funniest guy in the world," Reiss says.
Portrait of the Comic as a Young Man
The third of six children in an Irish Catholic family in Brookline, O'Brien excelled in English as a Brookline High School student.
But for O'Brien--like so many teenagers--high school was a time of angst and self-doubt, as he told members of BHS's Class of 1992 at their graduation.
"I had bad skin, my feet were too big, I thought everyone was looking at me and I didn't look right," O'Brien said. "Well, actually, I didn't look right."
In a 1980 Boston Globe article, a high school-aged O'Brien cited writing, history and politics as his three main interests. He served as managing editor of his school newspaper, The Sagamore, and interned for Rep. Barney Frank '61 (D-Mass.).
At age 17, O'Brien won a national writing award for a short story on the plight of a middle-class Irish teenager who wants to apply to college but knows his undertaker father expects him to join the family business.
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