'Poonster Gets the Last Laugh

Conan C. O'Brien '85 has made a career out of proving people wrong.

When "Late Night" producer Lorne Michaels, the mastermind behind "Saturday Night Live," tapped the unknown comedy writer to replace the legendary David Letterman, few thought he'd last long.

And when his show debuted in 1993 to lousy ratings and lousier reviews, most thought O'Brien's days in NBC's 12:35 time slot were numbered.

Many TV critics, such as The Washington Post's Tom Shales, quickly called for O'Brien's head.

To Shales, the 6 foot 4 inch comic was the weak link in what could otherwise be a decent program.

"Subtract this fidgety marionette from the Lorne Michaels production, and you have a fairly handsome talk show package waiting for a real entertainer to step in," wrote Shales just two days after the new host's debut.

And there were many alternative late night hosts waiting in the wings: Tom Snyder, Jon Stewart, Greg Kinnear.

Nearly seven years later, O'Brien is still on the air, and Tom Shales is singing a different tune.

"Conan O'Brien...has gone through one of the most amazing transformations in television history," a penitent Shales wrote in 1996.

By that point, O'Brien's ratings were up despite stiffer competition, and viewers and critics had warmed to his go-for-broke style, annoying laugh and unruly hair.

"They say Einstein didn't speak until he was nine. Conan didn't really speak until he was about 20," says Rodman Flender '84, who worked with O'Brien at the Harvard Lampoon, a semi-secret Sorrento Square social organization that used to occasionally publish a so-called humor magazine.

The lesson, he says, is that it's okay to be a late bloomer.

But there's another possibility: maybe O'Brien has always been that good--and the rest of us were just hopelessly behind when we knocked the red-headed giant.

Michael L. Reiss '81, a Lampoon alum who worked with O'Brien at HBO's "Not Necessarily the News" and Fox's "The Simpsons," argues that Shales and other converts are just covering up their initial error in judgement when they claim there have been recent improvements in "Late Night."

"The public's perception has changed more than the show itself," says Reiss, who is unwavering in his support of O'Brien.

"He's the funniest guy in the world," Reiss says.

Portrait of the Comic as a Young Man

O'Brien showed a lot of promise in his early years--but not necessarily in comedy.

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.

In the end, the student decides to throw his scholarship application in the trash.

No such fate was to befall O'Brien--his father is a microbiologist, his mother a lawyer--although at 17 he didn't know where he was headed for college.

"I'll take the best one that picks me," O'Brien said then.

Harvard picked O'Brien, and he matriculated in 1981.

It did not take O'Brien long to find the Lampoon's 44 Bow St. castle.

He landed a spot in the organization in the first semester of his first year--a considerable feat.

Even more impressively, O'Brien was elected president of the publication as a sophomore.

Reiss recalls working in New York and hearing "through the grapevine" that the Lampoon had elected a sophomore president. For as long as anyone could remember, the position had always been held by a junior.

"Everyone was curious about him," he says.

One day, Reiss called the Lampoon for some information, and O'Brien happened to pick up the phone.

While joking about O'Brien's odd first name (he is named for Gaelic priests, not barbarians), Reiss says he was taken aback by the new president's quick wit.

"Jeez, this guy is really sharp," Reiss remembers thinking.

Another former Lampoon editor, Al Jean '81, who now writes for "The Simpsons," says he and Reiss made a point to fly back to Boston in order to meet the new prodigy.

Not only was O'Brien a talented writer and artist, but he worked hard. According to Flender, O'Brien had an unusually large amount of quality material.

O'Brien's own memories of his college days at the Lampoon are a bit fuzzier.

"This was the '60s, of course, so we were doing a lot of drugs," he told The Crimson in February. "There was a castle. I used to eat all of my meals in Adams House."

The Lampoon is legendary for its pranks, and O'Brien's administration was no different--if he and his cohorts are to be believed.

Flender says he remembers an incident in which O'Brien successfully drained the Charles River using "a system of funnels."

"We killed the Dean of Students [Archie C. Epps III] once," O'Brien claimed in February.

According to Jean, when Burt Ward--who played Robin on TV's "Batman"--came to visit Harvard, Lampoon members dressed up as the Penguin and his crew and stole Ward's Robin suit.

This theft, which Jean says "actually happened," was successful--though O'Brien later returned the suit.

Richard J. Appel '85 remembers when O'Brien and friends interrupted a Core physics lecture by performing a "Particles-Quarks Ballet."

"I don't know how you dress up like a quark," admits Appel.

Appel stresses, though, that O'Brien's college career was about more than just pranks and the Lampoon.

Appel and O'Brien concentrated in history and literature, which is honors-only. According to Appel, O'Brien was an avid reader who was "interested in ideas."

"He took classes pretty seriously," Appel says.

He Works Hard for the Funny

But if O'Brien enjoyed reading Flannery O'Connor and studying the Civil War while at Harvard, when he graduated in 1985 he knew he wanted to write jokes.

So despite the pull of his tight-knit Boston-based family, O'Brien headed for the West Coast.

Reiss immediately snatched O'Brien for HBO, hiring him to write for the network's current event parody show "Not Necessarily the News."

In 1988, Michaels brought O'Brien back east to write for "Saturday Night Live." He earned an Emmy Award for Outstanding Writing in a Comedy or Variety Series in 1989.

By this time, Reiss had moved on to the animated hit "The Simpsons," and he wanted his fellow 'Poonster on his team.

"Conan was the first guy we wanted to have," Reiss says.

The show started with steady staff of eight writers, but Reiss brought in O'Brien when the show had two unexpected vacant spots in 1991. "What I could not believe about the guy is that he is funny all day long," Reiss says. "At midnight or 1 a.m. he'd still be funny."

When O'Brien was alone in his office, "he was still doing something kind of funny, just to make himself laugh."

And nobody worked harder than O'Brien. In only his third day on the job at "The Simpsons," he successfully pitched what became O'Brien's favorite self-written episode, entitled "Springfield Gets a Monorail."

Reiss says he considers the episode one of the best in the show's 10-year history.

"I wish we had him back writing at 'The Simpsons,'" Jean says.

The King of Late Late Night

In 1985, The Crimson questioned O'Brien, about to graduate, about his career plans.

"The perfect world would be where the 'Conan O'Brien Show' would be on, and you'd be reading my short story and wearing my designer jeans," O'Brien said.

It seemed unlikely. After all, while many Lampoon alums had gone on to careers in comedy writing or filmmaking, few actually made it in front of the camera.

But on April 26, 1993, less than eight years after he graduated from college, O'Brien saw his dream--or at least the first part of it--come true.

In that year, late-night legend Johnny Carson retired and a bitter competition for his NBC show erupted between late night hosts Jay Leno and David Letterman. When NBC chose Leno to fill Carson's shoes, an angered Letterman left the network--and his popular 12:30 show--for an earlier slot on CBS.

NBC was left host-less for its later show. Rather than go with an established celebrity, Michaels decided to take a chance with O'Brien.

Before 1993, networks had little luck with late, late talk shows hosted by men not named Letterman. Such diverse personalities as Pat Sajak, Chevy Chase and Arsenio Hall all tried and failed to get people to stay up. Chase's ill-fated show lasted only days.

So the media descended on O'Brien, trying to get a reading on the man who would have to fill Letterman's large shoes. He responded to the intense scrutiny with wit.

The show ran promotional ads poking fun at O'Brien's anonymity by having an announcer mispronounce his name as "Conrad O'Brien." The sad host shook his head and corrected him, "That's Conan..."

And O'Brien penned a humorous essay that ran in The New York Times on Sept. 13, the day his show premiered. The piece described a show that bombed badly and blasted the host (himself) as incompetent and bumbling.

Unfortunately for O'Brien, it was one instance in which life imitated art.

From its first night, "Late Night" was panned by the critics. Some took issue with O'Brien's interviewing style, others with his hair, laugh, nervous tics and long monologues.

Few had anything nice to say about O'Brien's debut, which closed with the host's performance of "Edelweiss," leading a Nazi and a nun in the audience to break down in tears.

O'Brien and sidekick Andy Richter braced themselves for the ax to fall.

But it never did.

Instead, as O'Brien put on show after show, the critics and viewers began to come around.

At first, critics were shocked.

"Ten months of Conan O'Brien. This alone is astonishing," wrote The Chicago Tribune's Jeff Perkins in July 1994, arguing that the show was just as bad as it had been at the start.

But eventually O'Brien began to win some real acclaim.

And by 1996, two million people were watching the show every night.

Tom Shales called "Late Night" "inventive, outrageous, satirical and often just spectacularly silly."

What else could be said about a show that regularly features the host and his sidekick engaged in silent staring contests as the audience looks on in awe?

Or "If They Mated," a segment in which computer graphics simulate the unlikely offspring of such celebrities as New York Senate candidate Hillary Rodham Clinton and former House Speaker Newt Gingrich (R-Ga.).

Or Triumph, the Comic Insult Dog, a hand puppet that threatens to poop on guests.

Or O'Brien himself, who is now, according to Shales, the most watchable personality on late night television.

O'Brien's Lampoon cronies say this was always the case.

"I thought it was funny from the start," Reiss says.

"I thought it was funny from the start," parrots Jean. "And it's still funny."

"Best show on TV," Flender says.

O'Brien has said he blames the show's initial failure partly on his inability to make proper use of Richter, who has since become a star in his own right.

Richter has decided that after seven seasons, he wants to strike out on his own to pursue an acting career.

On Friday night, May 26, he appeared in his farewell show--complete with a huge musical number and fans chanting "An-dy!"

For the moment, "Late Night" has no plans to replace Richter.

That's no matter to O'Brien. Reiss says the O'Brien's show may even be better without a sidekick--and if he needs someone to chat with, he can always talk up the band.

Richter's triumphant exit probably indicates that O'Brien is as on top of the world as a 12:35 a.m. comic can possibly be.

And it couldn't have happened to a more deserving guy, say his friends and co-workers. He has never let being the president of the world's oldest humor magazine, having a Harvard degree or starring in his own television show go to his head.

"It's nice to see nice things happen to nice people," Appel says.