The cigarette landed on an empty seat. Nobody was hurt, but Sammy Davis Jr. standing in the wings watching Dean from the side of the stage saw something in that moment that had nothing to do with the cigarette. He saw Dean’s face a half second after it left his hand. And that face was not the face of a man playing a bit, working a joke, doing the bit he’d been doing for 30 years where he played the lovable drunk who couldn’t quite hold it together. That face was something else.
That face was a man who had looked out at 14,500 people and felt absolutely nothing. Wait, because what you’re about to find out is not the story you think it is. And the part nobody ever talked about didn’t happen on that stage. It happened in a dressing room 2 hours later when Sammy walked in and found Dean sitting alone, holding something small in his right hand.
And the look on Dean’s face when he finally looked up told Sammy everything he needed to know about why this tour was already over before it had truly begun. It started in December 1987 at Chason’s restaurant in Beverly Hills. Frank Sinatra had called the meeting. He’d made the reservations, arranged the press, and when Frank Sinatra arranged a press conference, the press came.
Dean showed up in a tuxedo that still fit perfectly because Dean was one of those men whose body seemed to refuse the passage of time out of a kind of professional obligation. He was 70 years old. He looked 60. He sat between Frank and Sammy and smiled for the cameras and said the things you say when you’re announcing a 29 city national tour.
That it was going to be a hell of a time. That the three of them hadn’t lost a step. That America was going to get something it hadn’t seen since the old days at the Sands. Since the Kennedy years, since the nights when the marquee outside read Dean Martin, maybe Frank, maybe Sammy, and every single night was maybe. He said all of it.
He smiled through all of it. And when the cameras clicked and the reporters shouted their questions and Frank leaned over and said something into his ear that made Dean laugh, it looked exactly the way it was supposed to look. But notice this because one of the reporters in that room noticed it and wrote it down. And it only makes sense now looking back.
At one point during the press conference, a photographer asked the three of them to look toward the center camera, and Frank turned immediately, and Sammy turned immediately, and Dean turned a half second later than both of them, like a man who had been somewhere else for just that one moment and had to find his way back. It was nothing.
It was barely a thing. The photographer got his shot and nobody thought about it again. Nine months earlier, on March 21th, 1987, at approximately 2 in the afternoon, a Macdonald F4C Phantom 2 jet fighter assigned to the California Air National Guard, had lost spatial orientation while climbing through multiple cloud layers over the San Bernardino Mountains in California.
The pilot, Captain Dean Paul Martin, 35 years old, call sign Grizzly 72, had requested a left turn. Air traffic control authorized it. By the time the authorization came through, it was too late. Dean Martin’s son was gone by 2:15 in the afternoon. The body wasn’t found for 4 days in the snow on the mountain. Dean’s daughter, Deanna, later said that her father flew in a private helicopter that circled the mountain for hours before the search teams found anything and that when the call finally came, the sound her father made was not
a sound she could describe. She said she had never heard anything like it before. She said she hoped she never would again. Look at the math. Nine months between that afternoon on the mountain and the afternoon at Chason’s where Dean sat between his two oldest friends in a tuxedo that still fit perfectly and smiled for the cameras and said the things you say.
9 months and nobody in that room looking at that man could have told you what those 9 months had actually cost him. Frank knew. Frank had organized the tour specifically because Frank knew. He told Sammy before the press conference, “I think it would be great for Dean. get him out. For that alone, it would be worth doing.” Frank Sinatra, the chairman of the board, the man who ran the room in every room he’d ever walked into, had looked at his oldest friend and seen something that scared him.
And his answer, the only answer Frank Sinatra knew how to give, was to put Dean back on a stage. Because a stage had always been the place where Dean was most himself. A stage had always been the place where Dean could disappear into something larger than whatever he was carrying. And Frank believed with the conviction of a man who had built his entire life on that same principle that the stage would fix what was broken.
Frank was not wrong about the stage. He was wrong about which stage. Rehearsals started in February 1988 and the people who were there all said the same thing afterward in different ways and with different degrees of gentleness. Frank was sharp, Sammy was extraordinary, and Dean was somewhere else, not drunk.
That was the thing people kept coming back to because the assumption was always that Dean’s struggle must have had something to do with the drinking. The way the assumption had always followed him, but the people who knew him, who had worked with him, who understood the difference between the bit and the man, were clear about it.
Dean was sober, or as close to sober as he ever was, and he was still somewhere else. The eyes were clear, the distance wasn’t. The problem, one of the tours production staff said later, was the size of the stage. Dean had spent the last several years doing intimate shows in Las Vegas, small rooms, 2,000 people at the outside, the kind of room where you could see individual faces and hear individual laughs and feel the specific weight of a specific crowd.
He had built his entire performance style around that intimacy. The casual lean, the half turned joke, the moment of genuine eye contact with someone in the third row that made the whole room feel like an inside joke between friends. Strip that away, put him in a coliseum, put 14,500 people between him and the moment he needed to find, and something in the equation broke down.
But the tickets were sold. 29 cities, every show sold out within hours. The marquee at Oakland Coliseum Arena on the night of March 13th, 1988 read exactly the way it was supposed to read. The orchestra was tuned. The dressing rooms were stocked. And at 8:00 on a Sunday evening in Oakland, California, with 14,500 people on their feet before a single note had been played, Sammy Davis Jr.
went out first because that was the order they had agreed on. Sammy to open, Dean in the middle, Frank to close, and Sammy was incandescent, the way Sammy always was, moving like a man who had never once in his life been afraid of any room. Then Dean walked out, and the roar was something physical. 14,500 people who had waited years for this, who had bought the $40 tickets and driven in from three counties over and told their kids they were going to see history.
They gave Dean Martin everything they had the moment he appeared. And for a moment, for just that first moment, when the lights hit him and the sound hit him, and he stood there in the tuxedo with the red pocket square and the drink in his hand that he’d been carrying as a prop since 1953, something happened in his face that looked like the old thing, the real thing, the thing that had made him Dean Martin instead of just Dino Crocetti from Stubenville, Ohio.
He took a sip from the glass. He looked at the audience. he said in that voice, in that particular slur but precise cadence that was one of the great comic instruments of the 20th century. How long have I been on? The house came down. 14,500 people laughing at once is a sound you feel in your chest. And Dean let it wash over him for exactly as long as he needed to let it wash over him.
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And then he started to sing. For a while it worked. Notice this. because the people who were there, who wrote about it and talked about it afterward, all made a point of saying it. For a while on that first night in Oakland, Dean Martin was Dean Martin. The voice was not what it had been in 1964 or even 1974.
But it was his voice, and there was still something in it that no other voice could replicate. A quality of ease that was not ease at all, but the hardest one craft of 50 years. a man who had worked so hard to sound like he wasn’t working that the work had become invisible even to him. He moved through his set with the old looseness.
He got the laughs where the laughs were supposed to be. And then somewhere in the middle of a song, accounts differ on which song, and the uncertainty matters because it suggests that what happened next was not a planned moment, but a slipped one. Dean lost the lyric. Not the way you lose a lyric when you’re nervous, grabbing for the next word while your mouth keeps moving.
He lost it. The way you lose something when you realize mid-reache that it isn’t where you thought you left it. There was a beat of silence. The orchestra kept playing because orchestras are trained to keep playing through exactly this kind of silence. And then Dean found the next line and kept going. And most of the 14,500 people probably didn’t notice.
And the ones who did notice probably chocked it up to Dean’s character. The bit, the sleepy drunk who couldn’t quite hold it together. But it wasn’t the bit. And then later in the set, in a moment that nobody who saw it could explain as a bit, Dean reached into his breast pocket, pulled out a cigarette, lit it with a lighter he produced from his side pocket, took one drag, and flicked it, still burning into the audience.
Not a dramatic throw, not a staged moment, a flick, the kind of unconscious, contemptuous gesture a man makes when he is somewhere else entirely and his body is moving on its own. The cigarette landed on an empty seat three rows back. The section went quiet. 14,500 people in the space of about 4 seconds went from laughing to uncertain.
And in that uncertainty, you could hear something shift in the room. The collective recalibration of an audience that had paid $40 a seat to see something specific and was now seeing something else. Dean kept going. He finished the set. The crowd gave him a standing ovation because the crowd was generous and because Dean Martin walked on the stage in a tuxedo with a drink in his hand and some portion of the audience was going to give him a standing ovation regardless.
And because the human instinct when you are watching something go wrong in a way you can’t quite name is to applaud more loudly than you need to. As if the volume of the applause can make the wrong thing right. He walked off the stage. The backstage corridor was narrow and lit with the blue white fluorescent light that all backstage corridors are lit with.
The light that makes everyone look like a different version of themselves. And Dean walked through it toward his dressing room without stopping to speak to anyone, which was not by itself unusual for Dean, who was not a backstage talker, who had made it a point of professional pride to get off the stage and get to the room and get the door closed behind him.
People gave him space. People had always given Dean space because Dean was the kind of man who took it whether you gave it or not. Frank was still on stage closing the show doing what Frank Sinatra did in every room he’d ever closed. Filling it, commanding it, turning it into the kind of room that would always be described as the room where Frank Sinatra played.
Frank would hear about the cigarette from three different people before he reached his own dressing room. And what Frank said when he heard about it was not printable. And the dinner that evening ended earlier than it was supposed to end. And the spaghetti that was reportedly thrown during the argument that followed the dinner has passed into the kind of legend that can’t be confirmed and can’t be entirely dismissed.
But none of that is the part that mattered. The part that mattered happened before Frank’s argument, before the dinner, before the tour manager started making calls to find out whether they needed to start thinking about a contingency plan. The part that mattered happened when Sammy Davis Jr. knocked on the door of Dean’s dressing room.
After a long enough pause that he almost knocked again, heard Dean’s voice from the other side say quietly, “Yeah.” Sammy opened the door. Dean was sitting in the chair in front of the makeup mirror. The overhead lights making his reflection look slightly older than the man in the chair, the way mirrors in dressing rooms always do.
He wasn’t looking at the mirror. He was looking at his right hand, which was resting on his knee. And in his right hand was something small and metal that Sammy couldn’t immediately identify. Sammy came in and closed the door behind him. He didn’t say anything. Sammy Davis Jr., who had spent 60 years filling every room he entered with something.
Noise, movement, laughter, energy, the sheer force of a personality that seemed to expand to fill whatever space it was given. Stood in that dressing room and said nothing because he understood, looking at Dean, that nothing was what was needed. After a while, Dean looked up. “He used to call me before every show,” Dean said.
Even when he was stationed, he’d find a phone somewhere and he’d call and he’d say, “Pop, go get him.” That was all, just that. Sammy sat down on the edge of the couch near the door and still didn’t say anything. Dean looked back down at his hand. The small metal thing was a pair of pilot wings, the kind given to military aviators when they complete flight training.
Small and silver with an eagle at the center, the pin on the back worn smooth from years of handling. Sammy had never seen them before, but looking at them, he understood immediately what they were and where they had come from. And the understanding settled into the room the way heavy things settle slowly and without drama. 14,000 people out there tonight.
Dean said, “You know what the funny thing is? I couldn’t tell you what any of them looked like. I was up there for 40 minutes and I couldn’t tell you one face. He paused. Back when it was just the two of us, Jerry and me. We used to play rooms where you could see every face. Couple hundred people maybe. You’d know by the end of the first song whether you had them.
You’d know exactly what they needed. He turned the wings over in his hand. Those rooms you could feel when someone was having a bad night. You could feel it. You could do something about it. Sammy waited. He was 35. Dean said, “Did you know he got his pilot’s license at 16, 16 years old?” Something that wasn’t quite a smile moved across Dean’s face and left again.
I told him it was crazy. I told him, “You’ve got every reason in the world to stay on the ground. What do you need to be up there for?” And he looked at me. He had this way of looking at you straight on. No flinching. And he said, “Pop, you do your thing. This is mine.” Dean closed his hand around the wings.
He was right. That was his thing. I knew it then. I just didn’t want to know it. The dressing room was very quiet. Somewhere down the corridor, the muffled sound of the orchestra hitting the final chord of the evening carried through the walls and then was gone. “The show was good,” Dino, Sammy said.
“It was the first thing he’d said,” Dean looked at him. “Some of it was good,” Sammy said, because Sammy was a man who had spent his entire life in the honest business of performance, and he loved Dean too much to give him anything less than the truth. The beginning was good and then you left. Dean held his gaze for a moment. Then he nodded once.
The way a man nods when someone has said the accurate thing and accuracy is the only kindness that’s worth anything. Frank thinks the stage is going to fix it. Dean said. Frank loves you. Sammy said, “I know he does.” Dean stood up from the chair and for a moment he was just a 70-year-old man standing in a too bright dressing room after a show, which is one of the lonelier things a person can be.
Then he straightened and you could see him find the posture, the particular way Dean Martin held himself when he was in public. The slight backward lean, the ease in the shoulders, the thing that people spent 50 years trying to describe and never quite got right. Tell Frank I’ll see him at dinner.
Dean, I’ll see him at dinner. Sam. Sammy stood. He understood what was being said and what wasn’t being said. And he understood that Dean understood both and that there was nothing left in this room that needed to be spoken. He moved toward the door. Sammy, he stopped. Dean was looking at the wings in his hand. He didn’t look up.
He used to say when he was a kid, maybe 8 9 years old, he used to say he was going to fly so high nobody could see him. Just up there somewhere, out of sight. He paused. I used to worry about that. What kind of a father worries about his kid wanting to fly? He closed his hand again. Turns out he was right about that, too.
Sammy left without another word. The tour continued for three more shows after Oakland, Vancouver, Seattle, one more city after that. At each one, Dean walked out in the tuxedo with the red pocket square, and the crowds gave him everything they had, and he gave them back what he could, which was more than most men alive could have given.
but which was no longer the thing that the tour had been built around. The official story, the one released to the press, the one that appeared in every newspaper that covered the story, was that Dean Martin had suffered a flare up of an old kidney condition and had been admitted to Cedar Sinai Medical Center in Los Angeles on medical advice.
The press accepted it, the public accepted it. A few music journalists noted that Dean had looked less than his best during the Oakland show. But the consensus was that it was health, age, the natural attrition of a body that had been asked to do extraordinary things for an extraordinary length of time.
The people who actually knew said different things. One of them, a production hand who had worked a dozen Sinatra tours, said he’d passed Dean in the corridor after the last show, and that Dean had said something he never forgot. He didn’t repeat the exact words, but said Dean had made it clear the size of the room wasn’t the problem.
The problem was that the hunger for it, the particular aliveness that performing had always given him was gone. And standing in front of 14,000 people pretending otherwise felt like the one dishonesty he couldn’t make himself commit. He had been honest his whole life about the things that mattered. The casual persona, the drink, the looseness that looked like laziness, all of it came from a genuine place.
but performing because the machine expected it and Frank believed it would help. That was a different thing. That was the thing he couldn’t do. Frank and Sammy continued. Liza Minnelli stepped in and the tour became something else, something that was also good in its own way and the audiences still came and the reviews were still strong and Sammy Davis Jr.
was by every account extraordinary every single night. Sammy was diagnosed with throat cancer the following year. He died in May 1990. He was 64 years old. Dean didn’t perform again in any meaningful way after the tour. He played some smaller shows, fulfilled some commitments, appeared at some events, but the career, the thing Frank had hoped the tour would restore, never came back.
He lived quietly in his house in Beverly Hills. He went to his favorite restaurants. He was polite to the people who recognized him and patient with the people who wanted photographs and generous to the people who asked him for things. in the way that men who have spent their lives being generous continue to be generous even when they’ve stopped caring very much about most things.
He kept the pilot wings. His daughter Deanna said that she never once saw him without them after March 21st, 1987. He carried them in his right pocket every day, the way other men carry a watch or a phone or a set of keys, the thing your hand finds automatically without thinking when you need something solid to hold.
At dinners, at the rare public appearances, alone in the house on the evenings when he sat in the chair by the window and watched the light change over the hills. The wings were in his pocket, and sometimes his hand would find them and close around them, and sometimes it wouldn’t, but they were always there.
He died on Christmas Day 1995, alone in his home. The lights on the Las Vegas strip were turned off that night in his honor. Not by a mandate, not by an official announcement, but by the casinos and the clubs and the showrooms that had built their identities around the era he represented. Each one going dark on its own.
A city turning off its lights for the man who had helped make the lights worth turning on. He was buried with the wings still in his pocket. A captain in the California Air National Guard, 35 years old, had told his father that flying was his thing, the way singing was Dean’s thing. And Dean had carried that conversation in his right pocket for 8 years and would carry it in whatever comes after the small silver weight of a son who was right about himself, who flew as high as it was possible to fly, who knew exactly what he needed and went and got it. The
14,500 people in Oakland didn’t know any of that. They saw what they were supposed to see. The tuxedo, the drink, the joke about how long he’d been on, the voice doing its incomparable thing. Most of them got exactly what they paid for and went home satisfied. But Sammy Davis Jr. knew.
Sammy saw Dean’s face in the half second after the cigarette left his hand. And later that night, sitting in a two bright dressing room with a pair of silver wings between them, Sammy understood something that he carried for the remaining two years of his own life. something he mentioned once in conversation with a friend who shared it only after both of them were gone.
That the bravest thing Dean Martin ever did was not any of the things the public saw. It was walking out onto that stage on March 13th, 1988, one year after the worst day of his life, with the wings in his pocket and the mountain still in his chest and standing in the light long enough to let 14,000 people believe the thing they needed to believe.
That one song, that one more night of making it look easy. One look, one breath, one more time for them. If you enjoyed spending this time here, I’d be grateful if you’d consider subscribing. A simple like also helps more than you’d think. If this brought back a memory or a thought you’d like to share, leave it in the comments.
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