Frank Sinatra didn’t care for rock and roll. He didn’t like music that didn’t have a story he could understand. Popular music just wasn’t his thing and I didn’t know a single pop star he admired. His collaboration with Bono on “I’ve Got You Under My Skin” took Sinatra’s classic song through a time tunnel. It turned out to be among the most memorable cuts on Duets and put Sinatra in front of a whole new generation. In fact, at least one pop station deejay introduced the song by saying, “Many of you may not have heard of Frank Sinatra, but here’s Bono’s new recording.”
Bono, perhaps more than any other artist on Duets, was stretched to a completely foreign level. He actually had the guts to call Sinatra an “old fool” on the recording, and remarkably, Sinatra thought that was cool. While on the surface it might seem like they wouldn’t have much in common, both men liked to drink and hang out. Both were painters and they bonded as artists and singers. For all these reasons and more, Sinatra became very fond of Bono.
Sinatra sang on film and tape countless times, but modern music videos were new to him. He was seventy-six years old and still experiencing things for the first time. Bono went to Palm Springs to shoot the music video for “I’ve Got You Under My Skin.” We shot them meeting in a bar and riding in the back of a limo. At one point, Sinatra told Bono, “I don’t usually like guys who wear earrings.” I think Bono thought that was cool.
Eventually we produced a memorable, cross-generational video for the time.
“Don’t you know Blue Eyes, you’re never gonna win?” was delivered with a combination of attitude and admiration that Bono later expressed in his introduction to Sinatra at the 1994 Grammy Awards in New York City.
Sinatra, who already had a Lifetime Achievement Award and a Trustees Award, was about to receive the Grammy Legend Award, making him the first and only artist to receive all three “Special Merit Awards” from the Recording Academy. I had no idea when I walked into Radio City Music Hall that night that Sinatra would become the biggest newsmaker of the evening.
Sting performed. So did Whitney Houston, who won Record of the Year for “I Will Always Love You.” The Bodyguard soundtrack took Album of the Year, Toni Braxton won Best New Artist, and Natalie Cole sang a tribute to Curtis Mayfield. Then came the moment Barbara, Susan Reynolds, Hank Cattaneo, and I had been waiting for: Comedian Gary Shandling introduced Bono to present Sinatra’s award.
Bono had just lobbed an f-bomb while accepting his own Grammy for Best Alternative Music Album for U2’s Zooropa, saying, “I think I’d like to give a message to the young people of America—and that is we shall continue to abuse our position and fuck up the mainstream. God bless you.”
What most didn’t know was that before Bono introduced Sinatra, the two had met backstage in the greenroom, which had a fully stocked bar. Bono started pouring for both of them. What happened next was likely a combination of the young rock star trying to keep up with what he perceived of the legendary Rat Packer and the aging legend not wanting to be outdone by the brash new star.
Whatever it was, Bono was throwing ’em back at a pretty good clip and Sinatra was keeping up. Remember, Sinatra was the guy who believed in one ounce of alcohol per hour. In all my years with him, I never saw him take more than a sip or two of alcohol before going onstage. It wasn’t his way. That night I saw him take three or four shots. Seeing him break his own rules before a major acceptance speech had me concerned.
Bono went onstage smoking a cigarillo. He unfolded a piece of paper, swayed a bit, and barely looked up as he proceeded to read one of the most poetic and accurate tributes to Sinatra that anyone could have hoped for.
“Rock and roll people love Frank Sinatra because Frank Sinatra’s got what we want: swagger and attitude,” he said. “Rock and roll plays at being tough, but this guy well, he’s the Boss of Bosses, the Man, the Big Bang of Pop. I’m not gonna mess with him, are you?” He pointed to the audience.
“You know his story because it’s your story. Frank walks like America—cocksure,” he said, looking up from his script.
“To sing like that you’ve gotta have lost a couple of fights. To know tenderness and romance, you’ve gotta have had your heart broken… This is the conundrum of Frank Sinatra… Troubleshooter and troublemaker. The champ who would rather show you his scars than his medals.”
Bono broke into a smile and continued.
“Ladies and gentlemen, are you ready to welcome a man heavier than the Empire State, more connected than the Twin Towers [laughter from the audience], as recognizable as the Statue of Liberty and living proof that God is a Catholic.”
Sinatra walked out to a standing ovation that lasted more than a minute, with “Young at Heart” playing in the background. He walked to the microphone and took a bow. Bono handed Sinatra a crystal award. Holding it close to his chest, Sinatra said, “That’s the best welcome I ever had.” It was obvious he was deeply touched.
The audience was still standing and the applause resumed.
I was standing backstage with Cattaneo. He was overseeing the sound and lighting for the show and communicating with the control room via headset. I studied the expression on Sinatra’s face in the monitors, worried that the drinking would have an adverse effect.
“This is like being in baseball. The bases are loaded and you’re at bat and you don’t know what you’re going to do,” he said. There was so much emotion in his voice, and every sentence brought more applause.
“Isn’t that pretty,” he said, holding up the award. He really didn’t seem to know what to say, and at one point he took a deep breath and looked disoriented. For a minute I thought he didn’t know why he was there.
“This is more applause than Dean heard in his whole career,” he said. There was laughter, which seemed to encourage him. He was rambling now and I was growing more nervous with each word. He talked about drinking and then he looked for Barbara.
“Where’s my girl? There she is. Say hello to Barbara, everybody please.”
She stood and blew him a kiss.
“I love you. Do you love me?”
The audience again laughed. “I don’t quite know what to say to you. You know, there was no discussions about singing a couple of songs; otherwise if we had there would be an orchestra here with me. But apparently that’s not what they wanted tonight and I’m angry.”
More laughter. He shrugged his shoulders. “I’m hurt.”
He was becoming increasingly sentimental. When Sinatra became sentimental you never knew what was coming next. He might start talking about Ava or Nancy. I didn’t know what he would say, but I couldn’t stand by and let him melt down on live television.
“Tell them to go to commercial,” I said to Cattaneo.
He looked at me with wide eyes.
“Sinatra’s manager said we should go to a commercial,” he said into the headset he was wearing.
“I’m just happy to be here in the Apple,” Sinatra said. “I love coming back all the time. It’s the best city in the world.”
The director cut to a wide shot of the audience and the announcer came on as CBS cut to commercial.
Sinatra looked bewildered.
“You got a big pair of balls,” Cattaneo said, but I think he knew I did the right thing.
Susan Reynolds was backstage. She was one of the select few who knew what happened, and worked to handle the publicity fallout.
After the commercial break, Shandling apologized for the “mistake,” as he called it. When Billy Joel was onstage performing “River of Dreams,” he stopped midway and looked at his watch. “Valuable advertising time going by,” he said. There was a lengthy pause. “Dollars, dollars, dollars,” he added before resuming with the lyrics, “In the middle of the night.”
At the postshow EMI party, Barbara pulled me aside.
“What happened?” she asked, referring to him being cut off, not the impending meltdown.
“I have no idea,” I said. I didn’t have the heart to tell her the truth. Ultimately, the official word was that the production people made a mistake and cut to commercial by accident.
Sinatra never asked what happened, thankfully, and I was grateful to Susan for taking the heat and having to explain the situation to the New York media. The next morning, I hopped on a plane to Florida.
I didn’t answer my phone for a week, though I kept track of the news and television coverage. “Weekend Update” on Saturday Night Live did a skit about it, which tells you what a story it had become. And rocker Neil Young later commented in his memoir that he wanted more Sinatra and less of an introduction. Many people shared the same sentiment, wanting to give Sinatra his moment.
Maybe he would have been fine. Who knows? All I know is that I could never have lived with myself if he had truly become the “old fool.”