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Brookline's O'Brien returns to share his comic genesis

BROOKLINE -- Striding onto the stage at Brookline High School yesterday to face 1,000 expectant teenage faces, Conan O'Brien couldn't resist poking fun at his audience.

"What the hell are you doing here on a Saturday?" the late-night network TV star asked the students in mock exasperation. "Don't you people have lives?"

The host of "Late Night with Conan O'Brien," and one of Brookline's most famous sons, was the sole reason for the packed auditorium. Back home for a star-studded fund-raising dinner last night at the high school, he took questions from students for more than an hour. There were plenty of jokes about bullies and embarrassing moments in the high school cafeteria, but the celebrity guest also stressed a more serious message, about the students' potential to match his own success.

"Like a lot of you, I wasn't sure where I fit into high school," he said. "I wasn't a good athlete, I sucked in math, I wasn't very good in science. In a lot of ways I was an insecure person when I went to Brookline High School."

The valedictorian of his 1981 high school class, O'Brien studied American history at Harvard, led the Harvard Lampoon, and toiled as a writer on "Saturday Night Live" and "The Simpsons" before becoming the unexpected successor to David Letterman as host of the "Late Night" show on NBC. His show was panned in its first year -- "If I gave up after my first reviews, I wouldn't be here right now," he said -- but has achieved more recent critical success.

Wearing a purplish shirt under a blue jacket, O'Brien, 40, yesterday remembered himself as a tall and skinny teenager with red hair and acne. "Everyone here has better skin than I did," he said. A former high school newspaper editor and debate team co-captain, he feigned bewilderment at questions about his academic past. "My senior paper? I don't even remember -- I'm like 58 years old," he said in response to one question. Another student asked which elective courses he took in high school. "What are all of you talking about?" he said. "What's an elective?"

But he claimed to remember co-hosting his senior class show "with one custodian here, a guy named Whitey" -- a joke about the fugitive Bulger brother that most of the students seemed to miss.

O'Brien may have lacked female attention once, but yesterday, alone onstage, he could bask in adoration. "Hi, um, I love you," one student told him, exuberant and bashful. A senior described the 6-foot-4-inch O'Brien as "the handsomest man in America" after the event, when he was besieged with requests for autographs. One of the first students at the microphone confessed that she wasn't a high school student at all, but a Boston University student who had slipped into the school to see him.

Still another student, identified only as Alex, told O'Brien, "It's kind of weird seeing you up there," then asked the "Late Night" host for a favor: A girl he'd met, who loved the show, had given him her number -- but he'd lost it. Could O'Brien say hi to the girl on the air, and then read Alex's phone number?

"There might be a law about that," O'Brien said.

On fatherhood -- his first child, a daughter, was born this fall -- O'Brien had simple advice: "Wait a long time before you do that." Of Brookline, he said he misses the anonymity he enjoyed there. ("Not too far from here, but we won't get into that," he said in response to a question about where exactly he grew up; his parents still live there.) Of the Red Sox, he said, "if you're a fan, you can't change," and described having Yankees manager Joe Torre on his show as "like being behind enemy lines in World War II."

Red Sox general manager Theo Epstein, a 1991 Brookline High graduate, also was expected at last night's gala fund-raiser, along with fellow alums Michael and Kitty Dukakis and New England Patriots CEO Robert Kraft. Lew Schneider, a 1979 graduate and the executive producer of "Everybody Loves Raymond," was the emcee for the event, part of a $10 million fund-raising effort for innovative classroom approaches. Other well-known alumni of the high school range from radio personality Eddie Andelman (class of 1954) and "60 Minutes" host Mike Wallace (1935) to golf star Tom Harney and "Real World" cast member Flora Alekseyeva.

Students said they like to brag about the school's alumni, and some were even more impressed with O'Brien after seeing him in person.

"Now I'm even more of a fan, because when you're watching the show, you think it's all written," said Nikita Golitsyn, a senior. "Seeing him answer questions, you realize he's really funny."

Headmaster Robert Weintraub introduced O'Brien, and couldn't let the day end without making one joke of his own. "Don't you think it would be good to have a high school principal on your show?" he asked.

"I've got to go," O'Brien said.

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