The War for Late Night (18 page)

Jon was smart and athletic, ending up at William and Mary, where he played left wing on the soccer team. His only real entertainment background to that point was some horn playing in the high school band. At loose ends after graduation, he fell into a succession of odd—and odder—jobs, highlighted by one that made a real impression: as a puppeteer for children with disabilities. That tapped at least obliquely into the latent streak of humor submerged in Stewart, and the experience inspired him to set out to try stand-up.

It was a long and brutal initiation. Stewart spent close to a year working up the material—and courage—to appear at New York’s Bitter End club. When he finally did, he barely got through half the act before the flop sweat from the profound bombing he was delivering drove him from the stage—and almost out of the business. He stuck with it because at that point he wasn’t sure what else to do with his life.

For two years he worked during the day as a bartender at a Mexican restaurant in Manhattan, earning just enough to live on so that he could show up every night at the Comedy Cellar and go on as the last act. Every weeknight, somewhere near two a.m., Jon Stewart performed before the drunk and the lonely of the New York metropolitan area. “I sucked for two straight years,” Jon would later tell aspiring comics, partly as advice and partly as storm warning.

But slowly, incrementally, it came to him. Performing as Jon Stewart—he would later take the formal legal steps to abandon the name Leibowitz—he put on comedy muscle. His material got sharper, smarter. He landed some writing jobs, finally scoring a crucial gig hosting Comedy Central’s
Short-Attention Span Theater
. At around the same time, a young agent from William Morris, James Dixon, saw Jon performing stand-up. Sensing enormous appeal and potential in the obviously super-bright young comic, he signed him up. Much good—for both of them—would come from that initial connection.

Throughout the quick demise of his MTV and syndicated shows, his passage in and out of dalliance with the movies, and his unrequited affair with David Letterman’s production company, Stewart built his reputation with consistently impressive work. Everybody who worked with Jon came away thinking they had just encountered a driven, creative, and, yes, appropriately neurotic future star. All it would take was the right launch module.

The Daily Show
was precisely the rocket he required. Stewart’s sensibility—and his insight that the show’s comedy should have a harder edge about the folly of both those in the news and the people in the media who were covering them—transformed
TDS
first to more smart than silly, and then from awfully smart to damn brilliant. By 2000 it was celebrated enough to start grabbing Emmy nominations and ultimately collecting awards.

 

At the prime-time Emmy Awards ceremony in Los Angeles on September 19, 2004, Conan O’Brien sat with his group in the audience, close by Lorne Michaels, who, since he still retained an executive producer credit on
Late Night
, would take home a prize if Conan’s show won for best comedy or variety show. Michaels was also present because his meal ticket,
Saturday Night Live
, had been nominated in the same category.

Almost every season both shows would share the nominations with Letterman, perhaps Bill Maher’s HBO series, and inevitably with
The Daily Show
. Inside Conan’s camp the frustration mounted: starting in 2003 Jon Stewart’s show racked up wins every year in that category as well as the best-writing award, a streak that would continue right through 2009. As much as Conan and his group tried to shrug off Stewart’s success—topical and political humor always impressed awards types, they reasoned—it quietly drove them all nuts. They had all worked so hard, come up with so much distinctively original material, but they never got a shot to be recognized—because Jon Stewart was always there.

Michaels, who was losing every year as well with
SNL
, was more philosophical about Stewart’s winning streak. With his insight into Conan’s darker side, he knew this level of frustration with Stewart’s Emmy dominance could not be productive for the melancholic Irish comic. So, just as the telecast began, Lorne thought he should offer a helpful observation.

“Look around this room,” he said to Conan. “Do you see anyone who looks like you in this room? You know, there are a lot of very small Jews in the room.”

Lorne himself fit that description, though perhaps not as precisely as Stewart. But the joke was meant to let Conan know both that he shouldn’t take the Emmy voting too seriously and that Jon Stewart was no fluke. He was going to be around as a formidable player in late night.

Leno had a similar impression, which was why he feared a double-pronged assault from OʹBrien and Stewart. Leno refused to acknowledge any Emmy envy, however. He was never nominated anymore, which he put down to a typically perverse Hollywood dismissal of the merely popular. Jay would take numbers over trophies anytime. He had made that bargain with himself long before.

 

When Jay Leno was the most frequent—and popular—guest on David Letterman’s
Late Night
show in the 1980s, he eagerly embraced the role he had then carved out for himself: Mr. Cutting-Edge Comic. Letterman fans loved him for his ferociously funny harangues on the absurdities of life. Dave would simply set him up with “So what’s bothering you this time, Jay?” and Leno would be off, ranting about this idiocy (airline flights, bad movies) or that (corporate greed).

It gave him a profile in the business, which is what he wanted. But it wasn’t all he wanted. That level of success might make him money and attract favorable critical notices, but Jay was after the ultimate comedy career, and the models there were not Letterman or Richard Pryor or Sam Kinison. Jay consciously set out to have the career that a Bill Cosby or a Johnny Carson or—even more aptly—a Bob Hope had had. He wanted to be a comic for
every
audience.

That meant jettisoning Mr. Cutting Edge and slipping into Mr. Regular Guy. That persona was a snugger fit for Leno, anyway. He often joked about being “a great believer in low self-esteem,” but he came by the quality honestly.

One constant figure played a central role in Jay’s act, and in most of his stories about the formation of his character and views on life: his mom. Mainly Jay made merry references to his mother’s habitual embarrassment and emotional stringency, qualities he summoned up when discussing why he never wanted the title of his show to be the “Tonight Show Starring Jay Leno” as it had been with Carson, but instead insisted on the “Tonight Show
with
Jay Leno.” “Why would you want to call attention to yourself like that?” Jay would say, imitating his mother’s pinched Scottish accent. Of course, while the disavowal of “starring” also played well with that everyman image he sought to cultivate, the frequent citation of his mother’s cringing discomfort with his fame came from a deeper place.

 

James Douglas Muir Leno grew up in Andover, Massachusetts, feeling like a townie in a village dominated by its illustrious prep school, Phillips Academy. His exposure to that elite world gave Leno insight into what he concluded was the fundamental prep school mentality: class superiority. Jay himself was a child totally outside the WASP culture. His father, Angelo, son of Italian immigrants, was a popular insurance salesman for Prudential, and the family took pride—“That’s our company!”—when those “piece of the rock” commercials would play on television during shows of the fifties like
Victory at Sea
. His mother, Cathryn Muir, had survived a difficult childhood. She was sent to America from Scotland at age eleven to live with an older sister, because her mother had abandoned the family for a younger man and her father couldn’t afford to take care of all his children at home. Her formal education never extended past second grade. As Jay saw it, the experience had left her with an air of sadness that permeated her life.

Jay was born when Cathryn was forty-one, and his only sibling—a brother, Patrick—was ten years older. Jay acknowledged that he had never been close to Patrick, which had in part to do with their age difference, but also with the fact that Patrick was remarkably gifted academically. He was one of the top students in New England in high school and won an ROTC scholarship to Yale. After graduation he became an army officer, serving in Vietnam, and then it was on to law school. For a woman who never had a chance to get beyond second grade in elementary school, this outstanding, high-achieving son was naturally a source of huge pride.

At the same time that she basked in the glory of Patrick’s intellectual accomplishments, Cathryn Leno found herself often trudging off to school in Andover to hear about the latest embarrassing tribulation her younger son had brought upon the family. Teachers discussed Jay’s lack of attention and his apparent interest only in cutting up and amusing his classmates. The highlight of this experience, as Jay wove the tale (and fair context demands a note that Jay can be a world-class fabulist in the service of a humorous story), took place with a guidance counselor in high school, Mr. Neal, who decided that Cathryn had to be brought in for a conference. Jay always claimed he “overheard” the subsequent conversation: “Mrs. Leno, have you thought of taking Jamie out of school? He works at McDonald’s now and he seems to like that. Maybe he would do better at something like that. You know, education’s not for everyone, Mrs. Leno.”

As Jay remembered it, his mother was furious, telling Mr. Neal she had never heard of a guidance counselor suggesting a child be taken out of school. “Well, he’s disruptive,” the counselor complained. And then his mother took a stand, saying she was not doing anything of the sort and Jamie would stay in school to get his high school diploma.

Whether actually diagnosed or not, Jay made reference to his school difficulties by explaining, “I’m a little dyslexic.” His mother’s reaction to this was what Jay came to call her mantra: “You know you’re going to have to work a lot harder than the other kids to get the same things they have.” Leno seared that advice into his psyche. If he wasn’t as gifted as other kids—later, other comics—he would hit them where they might be weak: their work ethic. Leno especially loved to tell one story about his early days as
Tonight Show
host. He was at his post at home, as usual, writing jokes for the next day’s monologue, when he turned on the TV and saw a competitor. (Jay didn’t mention the name because he had resolved his differences with the rival, and good relations carried enormous weight with Jay, but it was pretty obviously Arsenio Hall.) “There he was sitting at the Lakers game,” Jay recalled. “And I thought, ‘Got ya! I’ll have a monologue tomorrow night and you won’t.’ And you know what? He didn’t.”

For Jay, the job always seemed to be as much about the self-abnegation involved in the effort as the effort itself: “It just seems like common sense. If you go to a party, or go out drinking, I win. It doesn’t seem that hard to understand. I’m amazed at people who can’t get that.” (Jay swore that he had never consumed an alcoholic beverage in his life. Of course he never took drugs, either, and, he said, he steered clear of caffeine as well.) How much of this attitude was a function of his relationship with his mother was always difficult to guess for those close to Jay, because Leno rarely exposed his emotions. But Jay brought his mom up often, on stage and off, and usually in the context of how repressed she was.

Like in his story about Carnegie Hall. As his career was taking off, thanks to his many breakthrough appearances on Letterman (sixty, he estimated at this point), Jay was booked in the hallowed New York concert venue. At first, he said, his mother found this simply astonishing. “Why are you going to be in Carnegie Hall?” he quoted her. “She thought it was a mistake.”

But of course he wanted his parents at such a prestigious show, and he got them excellent tickets in the third row back, right in the center. Behind them was a row of seven or eight college-age guys. “These guys knew all the bits from watching Letterman,” Jay said. “So whenever I started something they recognized, these guys would go
woo, woo
and start to laugh and applaud.” Jay threw himself as usual into the bit but could not help noticing from the stage that his mother was turning around in her seat.

“She starts to go, ‘Shush! Shush!’ She’s trying to shush them.”

Appalled, Jay stopped his act to speak out to his mother. “Mom! You don’t shush people.” He realized it was another example of his mother being somehow humiliated and embarrassed by the attention he was getting. It made her completely uncomfortable.

Her discomfort seemed amplified when the contrast between her sons grew wider. Patrick’s life took unexpected turns, all unhappy in various ways—his marriage, his career. Jay, meanwhile, thrived. He started making solid money as a comic at a remarkably young age and was able to buy a house before all the other young comics in the LA scene at the time. He got on television. He was, of all things, booked into Carnegie Hall.

And then,
The Tonight Show
beckoned. It should have been a glorious accomplishment to share with his family, but it didn’t quite go that way. Jay sensed that Patrick had issues accepting his kid brother’s success. And his mother seemed to resist expressing a lot of joy about it as well. Jay, making millions, could afford to give his parents anything, but that became a sensitive area. Sometimes Jay would return home to Andover with an expensive gift for his mother—a piece of costly jewelry, for example. Jay would present it to his mother, who would quickly get fluttery and say, “Don’t tell your brother you bought this,” and then would run and hide the gift away.

Jay would explain all this and say he understood it; his brother had to feel cheated in certain ways. Patrick was stuck with the Scottish traits in the family; Jay inherited the Italian. (That’s where the good teeth and fantastic head of hair came from.) Patrick became a worrier, stressed over everything in his life. It only swelled the cloud of sadness that hung over his mother.