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As for the defendants, prosecutors dropped the drunk-driving charges against Dee Dee after she spent twelve hours in a special alcohol-education program. Hugh was charged with lewd conduct in a public place and fined $1,180. He got back together with Elizabeth Hurley, though they would announce an amicable split five years later. His encounter with Divine Brown, which cost him $50, seemed to have little effect on his successful film career. And Divine, whose real name is Stella Thompson, was fined $1,150 for parole violations and sentenced to 180 days in jail. She eventually left the life of prostitution, thanking Hugh for “changing” her life. But her story wasn’t exactly Disney material. She parlayed the scandal into a financial bonanza, earning more than $1 million from media interviews by giving graphic details of the incident. For the record, we didn’t book her.

After Hugh Grant, Jay became the go-to host for fallen celebrities who wanted to come clean. In 2009, singer Kanye West made an apology for upstaging country singer Taylor Swift at the MTV Video Music Awards. As she was accepting an award, Kanye grabbed the microphone from her and argued that Beyonc
é
was more deserving of the honor.

“It was rude, period,” Kanye told Jay. Kanye was at a rare loss for words when Jay asked him what his late beloved mother Donda would have said about his behavior. Media critics questioned the appropriateness of Jay’s question, but he had met Donda. And he routinely challenged guests about their parents’ reactions to questionable behavior. Besides, Kanye had agreed to answer the question. Then, in July 2013, Kanye took back his apology to Taylor, telling the
New York Times:
“If anyone’s reading this waiting for some type of full-on, flat apology for anything, they should just stop reading right now.” When Kanye was reminded he had already expressed contrition, he implied he only did it because he had succumbed to peer pressure. Kanye’s confused and pathetic attempt to take back his apology only served to bolster Hugh Grant’s genuine
mea culpa.

In July 2013, Jay asked Eliot Spitzer: “How could you be this stupid?” The question had a ring to it, much like “What the hell were you thinking?” And it resonated with the press much like the one directed at Hugh Grant. The dishonored
former New York governor came on the show to express regret for having to resign from office five years earlier after spending thousands on a high-end prostitute. He was planning to make
a political comeback by seeking the office of New York City comptroller and wanted New Yorkers to understand he had been humbled by his personal mistakes. Spitzer answered Jay’s blunt inquiry this way: “People who fall prey to hubris end up falling themselves. And this is something that I think infected me. And the fall from grace is incredibly painful and is something through which you learn.”

By sheer coincidence, Bill Hader, who did an impression of Spitzer in a 2010 comedy sketch on
Saturday Night Live,
was his fellow guest. Spitzer referred to the comedian as his “long-lost twin who got all the talent” and said: “I usually hit the remote when I see him.”

While big celebrity
mea culpas
were a hallmark of the Leno years, they were very rare. On any given day, actors pitching their films and TV shows were our stock-in-trade. Naturally, our goal was to bring in the biggest stars, but sometimes the process could get complicated. In general, movie stars mattered more than TV stars. However, only about ten movie stars could be counted on to improve the ratings. Even they didn’t always come with a guarantee. As the number of talk shows increased, big stars made the rounds to promote their films, decreasing their value to us. Naturally, we tried to book them before any other show, but that wasn’t always possible.

Like monologue jokes, the best guest bookings were topical: actors in current, popular films and televisions shows and people with “buzz” created by critics. We learned not to get too far ahead of the curve. Frequently, viewers’ awareness of the latest films and “hottest” actors lagged behind the critics by several weeks. So we often passed on rising but still relatively unknown stars, who would have done nothing for our ratings. Instead, we allowed, and even encouraged, them to do other, “smaller” shows first. Sometimes we took a risk on a young, relatively unknown but promising actor to establish a relationship with them before Letterman
did, even though such a booking usually resulted in lower ratings. The idea was to reach out to younger viewers in the coveted eighteen to forty-nine demographic. We considered this the cost of doing business, an investment in the future, though it didn’t always pay off. Young stars often suffered from a strange case of memory loss when it came to remembering who gave them their big break. But sometimes we were pleasantly surprised.

Shia LaBeouf was a sixteen-year-old comedic actor appearing in a Disney Channel sitcom called
Even Stevens
when my teenage daughter, Melissa, brought him to my attention. A year later he was starring in his first feature film, Disney’s
Holes,
which I watched with Melissa. By then, she was insisting Shia would be a major star some day. I agreed with her and invited Shia on the show. He was as funny as any comedian and he did, indeed, become a Hollywood celebrity after appearing in such films as
Indiana Jones and the Kingdom of the Crystal Skull
and the
Transformers
trilogy, and we invited him back many times.

Anne Hathaway was an eighteen-year-old sophomore in college when we booked her for
The
Princess Diaries
, her first feature film. She remained loyal to the show, making appearances to promote subsequent films, including
Les Mis
é
rables,
for which she won an Academy Award in 2013.

Lindsay Lohan made her first and best appearance with Jay at age twelve while promoting her film debut in Disney’s remake of
The Parent Trap
, which was shot in London. I remember how cute and innocent she looked as she told Jay how much she disliked British food and how thrilled she was to discover they had McDonald’s in London. She was also feisty: when Jay mistakenly introduced her as Leslie Lohan, she said, “Hi, Jay Lemon!” She went on to become a loyal guest, though her return visits were often sad occasions. Stories about her troubling drunken behavior frequently turned up in the press. Like Hugh Grant, she apologized to Jay for her profligate lifestyle and promised to redeem herself. But unlike Hugh, she didn’t. In 2007, she cancelled a booking the day she was scheduled to appear after being arrested the night before on suspicion of drunk driving. Someone suggested we replace Lindsay with comedic actor Rob Schneider dressed in drag, playing her. He came out wearing a blonde wig, a black dress, and an alcohol-monitoring bracelet like one Lindsay had worn strapped to his leg.

While I was partly responsible for booking Rob, I thought his performance was tasteless, mean, and unfunny, a trip down the low road. I remembered when Lindsay was a freckle-faced kid, and now she was a young adult, possibly headed for a tragedy. Like many young actors, she grew up on movie sets and never had a childhood. Ironically, Jay once asked her if she ever regretted not taking time off from her acting career to just be a kid. She told him that at age twenty-six, she still felt like one. It was an awkward moment.

As time went on, we were booking fewer actors and more newsmakers. Interviews with presidential candidates during primary and presidential elections not only boosted the ratings but also resulted in heavy news and social media coverage. Timely appearances by sports heroes brought energy and excitement to the show like no actor could. Journalists and commentators also became frequent guests, as Jay was a news junkie who watched cable news in his office all day.

But even newsmakers never came with a ratings guarantee. Only animals could be counted on to bring in consistently high ratings, usually beating the biggest movie stars and celebrities on the
Late Show with David Letterman
.
Like the audience, Jay loved critters and furry creatures, particularly the big cats, and he was fearless around them. The humans who presented our animal guests, known as “animal ambassadors,” were just as important as the animals. The best ones, who knew how to balance their dual role as educators and entertainers, made up a small, elite group that included Joan Embery, Dave Salmoni, Julie Scardina, Jarod Miller, and the late “Crocodile Hunter” Steve Irwin, who was a worldwide star in his own right. Irwin made
Tonight
his late-night home. He and his animals ranked among our all-time most popular guests, and their appearances were more crucial to Jay’s success than any Hollywood celebrity.

Eventually, Steve pressed us for a sit-down chat with Jay without critters, which we rejected at first, believing the audience would resist the idea. We eventually gave in, booking Steve as a solo act. He didn’t disappoint us or our viewers as he regaled Jay with a very funny story about his newborn son Robert. Steve and his wife, Terri, had been hoping to provide a brother for their daughter, Bindi. He told Jay that the key to having a boy is to keep your testicles cool, which he did by wearing plastic-mesh underwear. While telling the story, he held up a mesh bag containing two onions. Fellow guest Catherine Zeta-Jones could barely contain herself.

In 2006, Steve died in a tragic accident while swimming with stingrays. Jay gave his friend an on-air tribute and wrote an obituary in
TIME
magazine: “He called himself the Crocodile Hunter, but Crocodile Preserver was more like it. He taught kids—and all of us—that not just the cuddly animals are special. And he was the best ambassador Australia ever had.”

On September 19, 2005, we turned to animals in an act of desperation to counteract a huge booking Letterman had just scored: Martha Stewart in her first late-night guest spot after serving a five-month prison sentence for insider stock trading. Our original lineup of guests that night was Benjamin Bratt, Nicollette Sheridan and B.B. King. Benjamin was a fine actor but not a huge star. With him as lead guest, we faced a ratings disaster against “M. Diddy” (Martha’s nickname among fellow inmates). We rarely cancelled or postponed a guest as a matter of policy, but this time we knew we had to make a change. No one mentioned Hugh Grant by name that day, but we were all aware that if he could make us number one in one night, Martha could do the same for David. So we booked animals along with animal ambassador Jarod Miller. We offered the second spot to Benjamin, who declined to follow animals and was re-booked as lead guest on October 17, his last appearance on the show. Steve Carell, then a rising new star, agreed to go second, and we bumped Nicollette Sheridan.

The changes ruffled some feathers, but they worked. Facing near impossible odds, we led with animals and won the ratings battle against
Letterman
and
Martha
by .4 of a point, approximately a half-million viewers. I’m just grateful our original lineup didn’t include a big-name Hollywood celebrity. We probably wouldn’t have cancelled such a person, and Martha would have destroyed us.

Chapter Four

Guests

Next to Jay, his guests were the most important part of the show. They got paid about $500 per appearance, union scale, but most didn’t come for the money. It was peanuts to them. They were selling something: a film, a television show, a book, or even a presidential run—which was a little scary when you think about it. They weren’t employees who could be fired for doing a bad job. They had no skin in the game.

Our success depended on people we had absolutely no control of; we were essentially turning the show over to them during their appearances. That’s why we vetted, as much as possible, what guests would be discussing during their interviews and why we invited the best ones back often. Most of the time our approach worked.

The best guests understood they couldn’t just hawk their wares. They knew they had to put on a good performance by telling great stories. While they often appeared to be having a casual conversation with Jay, many spent hours developing material for their interviews. We were grateful for their efforts, which helped take the burden off Jay.

The quintessential guest was comedian Billy Crystal, who appeared on the first show, May 25, 1992. He and Jay had known each other for twenty years at the time, and they looked like two friends chatting and clowning around during the segment. At one point, Billy pulled out a lyric sheet and began singing a musical parody to the tune “You Made Me Love You”:

You made me first guest.

I didn’t want to do it.

My agent really blew it.

I like your set, but

That picture of the sea now,

It makes me want to pee now.

. . . I’m proud to be your first guest.

That same night, Jay asked Billy to do his last show. He promised he would, and twenty-two years later he made good on his promise. Billy showed up on February 6, 2014, to do another music parody as well as a tribute done to the tune of “So Long, Farewell,” from
The Sound of Music.
He was joined by the “Shut Your Von Trapp Family Singers” as well as Sheryl Crow, Carol Burnett, Oprah Winfrey, Kim Kardashian, NBA star Chris Paul, and Jim Parsons.

Billy called Jay “America’s night-light” and then invoked the name of his predecessor, Johnny Carson: “You were handed the baton by one of the all-time greats. But once it was in your grasp, you ran the race.” Billy gave Jay a touching sendoff, just as he had given him a rousing kickoff. It was comforting to know we had a real pro on the first and last shows. But there were 4,608 shows in between, and not all guests could be as good as Billy. In fact, most of them weren’t. That was the challenge.

Most guests were actors. And as odd as it may seem, many struggled with the idea of doing a talk show. These were people who read scripts for a living, pretending to be other people. They didn’t seem to have life experiences of their own and often admitted their lives were uneventful and boring. My plumber actually had better stories than many of them. The guests I dreaded the most were the ones who said: “Let’s just wing it. Jay can ask me anything.” On the surface it sounded great, but they didn’t mean it. What they were really saying was they couldn’t think of anything to talk about and didn’t want to try. My job as a producer was to help them get ready for their interview by doing a so-called pre-interview. I usually started by reminding them Jay was a workaholic who thoroughly prepared for his own interviews on other talk shows. Winging it was never an option for him.

With many actors, I had to go over the basics of storytelling. It’s an art, but it’s not complicated. And it hasn’t changed much over the centuries. Johnny Carson had this advice for his guests: “Tell them what you’re going to say. Say it. Then tell them what you said.” Johnny didn’t actually come up with that idea. Aristotle did. A good story has to be simple, clear, and consistent, and it should have a beginning, a middle, and an end. The world’s greatest tales follow this ancient formula. I told my guests to imagine they were at a dinner party talking with friends. And I asked them to come up with three interesting, humorous topics and be prepared to talk about them at the party. The pre-interview usually worked well, but there was one notable exception.

In 2002, Christian Bale, an extraordinary actor, abruptly ended a pre-interview with me and cancelled his appearance on the show because my questions were too personal. I had asked him where he grew up (Wales), how big his family was (three sisters), and what his first gig was (a Pac-Man cereal commercial). I was amazed that a major star like Christian, who would win an Academy Award in 2011, didn’t seem to have even a basic understanding of how
The Tonight Show
worked. I understand he’s very protective of his privacy, but really; he’s also a public figure. I just don’t understand it. Still, I was glad he dropped out, thus averting an awkward on-air exchange with Jay.

Jim Caviezel, who turned in an Oscar-worthy performance as Jesus in
The Passion of the Christ
in 2004, had put a lot of thought into his upcoming interview with Jay but still needed a little guidance. He said he had recently visited the pontiff and had some great pope jokes. The trouble was, they weren’t funny. I suggested he leave the jokes to Jay, but I could tell he was disappointed. Believe me, it wasn’t easy saying no to the guy who had just portrayed Jesus better than anyone else I had ever seen. I knew he had much stronger material. He had literally been struck by lightning while filming the Sermon on the Mount scene. The skies were stormy, and he sensed an eerie vacuum as his hair stood on end. Then he was lit up like a Christmas tree. His eyes got very bright, and crew members saw flames coming out of the sides of his head. While this was happening, Jim saw what appeared to be a pink, static color and he heard a deafening sound like a jet engine. The strike left him stunned but—miraculously—unhurt. He joked that he looked up, as if to heaven, and all he could think to say was, “What, you didn’t like this take?” I told Jim that his story would have been too good to be believed if his film crew hadn’t witnessed it. But, then again, he was “Jesus.” How could he be lying? I strongly advised him to go with it and lose the jokes about the Pope. Jim reluctantly agreed, and I’m glad he did. I heard thousands of anecdotes over the years, but I believe his lightning strike tale was the greatest story ever told on the show.

Jay usually didn’t like to discuss the “craft of acting,” which he thought was pretentious. He made exceptions for people like Jason Alexander, who could make anything funny. Jason, best known for playing George Costanza on
Seinfeld,
said he followed one basic practice as an actor. Whenever he had a difficult scene to play, he imagined he was passing gas. That facial expression covers the whole spectrum of human emotions, including sadness, pain, lust, compassion, sympathy, concern, and confusion.

Oscar-nominated British actor Ralph Fiennes was not a fan of the Harry Potter movies until he agreed to play the evil Lord Voldemort, starting in the fourth film. When Jay asked Ralph why he took the part, he said he only did it after his two nephews got excited when they learned their uncle might be in a Harry Potter film. It was Ralph’s idea to shave his head for the role rather than wear a bald cap. A friend told him he looked tough as a bald guy, which he liked because no one had ever described him that way before.

Some actors were complicated, like Teri Hatcher. I called her Teri One and Teri Two, though not to her face. Teri One was charming, smart, witty, and flirtatious. You couldn’t make up a more perfect guest. Teri Two was moody. She would call me late the night before her scheduled appearance, scream at me for not having better ideas, and then hang up. The next day she would come to the show as Teri One, acting as if nothing had ever happened. Then she would put on an outstanding performance. I was intrigued by the behavioral patterns of the two Teris. They had an inverse relationship: the wackier Teri Two acted, the sweeter Teri One became. In spite of her eccentricities, I like Teri and can’t help but smile when I think of her portrayal of Susan as a deeply conflicted character on
Desperate Housewives.
Teri played her perfectly.

As time went on, we added more diversity to our lineup with politicos, singers, authors, and even reality TV stars. Some of our best guests were sports people, many of whom were natural entertainers. Charles Barkley, NBA hall of famer and TNT commentator, was a total goofball. You couldn’t help but laugh at anything he said, even if it wasn’t funny. He especially loved making fun of his own golf game. He once talked about playing in a celebrity golf tournament in Lake Tahoe, California, where he finished 80th out of 81. As he was describing his struggles with his golf swing, Jay called for video of Charles muffing a fairway shot, which advanced the ball only a few yards. Ironically, his golf coach was one of the best in the world—his friend Tiger Woods, who compared his swing to a “speech impediment” he called “the yips.” When Jay asked Charles what that meant, he answered, “That’s what you get when you can’t play golf anymore.” The joke made no sense, but it got huge laughs because Charles said it as only he could.

Singers usually had great stories about the road, and Stevie Nicks of Fleetwood Mac fame had the best one of all, telling Jay about the time her tour bus broke down on the Grapevine section of the I-5 north of Los Angeles. The fan belt had broken, the driver didn’t have a spare, and the band was late for a gig. What to do? Stevie suggested a pair of her pantyhose as a quick fix. It would be risky, as the Grapevine has many steep ascents and descents and has caused many overheated radiators. But desperate times call for desperate measures. The driver attached Stevie’s makeshift fan belt to the pulley, started the engine, and the band got to its scheduled performance on time.

Country singers had the best tour buses. Decked out with every modern convenience, almost all included big screen TVs and Wi-Fi. Many didn’t even use the show’s dressing rooms. Instead, they just hung out in their buses. Willie Nelson’s bus was the gold standard. Featuring beautiful, original Western murals and warm wood paneling, it was homier than most homes. Willie was the consummate host, always offering food and drinks. He once asked me to join him in smoking a joint, which I declined. But I think I actually got a little high.

The late Johnny Cash, known for his deep, resonant vocal timbre when singing such hits as “Ring of Fire,” “I Walk the Line,” “A Boy Named Sue,” and “Orange Blossom Special” told Jay he had a high-pitched tenor voice as a teenager. Then at seventeen his voice changed after putting in a long, hard day on the farm. At the end of the day he returned home and started singing an old gospel song. All of a sudden, his voice dropped an octave. His mother said, “Who’s that?” even though she knew who it was. When Johnny replied, “That’s me,” she simply said, “Keep it up.” And from that day he did.

Stephen King, the great horror novelist, was an accomplished, witty storyteller. He admitted to Jay that he slept with a night-light on, even though he didn’t believe anything was hiding under his bed. He also made sure his covers were always tucked in, which prevented non-existent monsters from getting in. He acknowledged his behavior appeared to be odd but insisted he was just taking reasonable precautions. Unfortunately for the show, Stephen never came back to our studio in Burbank because he was afraid of flying.

Cherie Blair, the wife of former British prime minister Tony Blair, told Jay how she became pregnant with her fourth child, Leo, while staying at Balmoral Castle during a visit with Queen Elizabeth II. She had left her contraception at home because she was afraid a royal maid would find it. She was forty-four at the time and assumed she would be safe, “and of course God was obviously laughing at me because nine months later along came Leo.”

Sometimes a good story is as simple as a name. In 2013, reality TV star Kim Kardashian
and singer Kanye
West
named their baby girl North West. As one would expect, Jay and other comedians made many jokes about it. But the story had an unexpected twist. Kris Jenner
, North’s grandmother, came on the show and said Jay was responsible for the name. Six weeks earlier, Jay was interviewing a very pregnant Kim
about a rumor that Kanye
favored the name North. She dismissed the rumor, saying she was partial to Easton (West). According to Kris
, her daughter had second thoughts after talking with Jay: “This is a true story, and I am not messing with you,” Kris
said. “She called me and she goes . .
. I never really took it seriously. I didn’t think about it. And, mom, after Jay brought it up, I think I want to name the baby North.”

“I think you’re responsible,” Kris said, pointing to Jay. “So, it’s my fault?” he replied.

True moments of spontaneity were rare at
Tonight
and in all of television, inherently a crisis environment. The job of producers is to keep chaos contained by controlling as much as possible. Spontaneity was fraught with too many potential dangers. Even a few seconds of substandard programming could result in thousands of people reaching for their remotes. But sometimes things so bizarre and unexpected would happen on the show that they were compelling, albeit sometimes embarrassing. These moments often became show highlights, including the greatest train wreck in the history of
The Tonight Show:
In 1993, NBC executives decided to have Jay do an entire program live and on location in Boston with the cast of
Cheers,
following the beloved NBC sitcom’s final episode after an amazing eleven-year run. The show would originate from the historic Bull and Finch Pub, the inspiration for both the sitcom and its set. It all sounded terrific. All of the cast members except one committed to be there, including Ted Danson, Woody Harrelson, Kelsey Grammer, George Wendt, John Ratzenberger, and Rhea Perlman. But after hanging out at the bar all day, most were intoxicated by show time. Besides, this was like a wrap party to them. And as Jay attempted to interview the cast, they were giggling and shooting spitballs at each other, which they frequently did on their own set. Jay repeatedly apologized for their drunken behavior, which seemed only to emphasize the fact that he had lost control.
Boston Herald
TV critic Monica Collins, who was at the bar, said all the cast members but Rhea Perlman behaved like “idiots” and “jerks.” Obviously, this critic had never been to a wrap party.

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