Introduction
Among the great style icons of the mid twentieth century, Dean Martin stood at the center of gravity. He was the sun around which the Rat Pack revolved. Effortless charm, half lidded eyes, a relaxed grin, and the carefully cultivated illusion of a man forever floating through life with a glass in hand. On stage in Las Vegas, especially beside Frank Sinatra, Martin perfected the image of casual excess, a public persona so convincing that it became myth.
But strip away the tailored suits, the casino lights, and the rehearsed drunken act, and another Dean Martin emerges. In his haunting recording of What’ll I Do, the Irving Berlin standard, Martin reveals a vulnerability that clashes sharply with everything the public thought it knew about him. This is not the entertainer winking at the audience. This is a man left alone with a question that has no answer.
Listening to this performance creates a strange psychological tension. The image is familiar. Dean Martin appears calm, almost amused, as if he is in on a joke the rest of the world has yet to understand. Yet the sound tells a different story. His voice carries loneliness and quiet devastation. It is the collision between a public mask and a private reckoning, a rare three minute window into the inner life of a man many close to him described as deeply private.
The song was recorded in 1960 for the album This Time I’m Swingin’!, an album whose upbeat title feels almost ironic in hindsight. Much of the record is filled with lively arrangements and playful confidence. Then suddenly everything stops. What’ll I Do slows time to a near standstill. The arrangement by Nelson Riddle removes brass and spectacle, replacing them with restrained strings that seem to close in around the singer. There is no escape route here, no place to hide.
What makes Martin’s interpretation so powerful is restraint. He does not overpower the song. He does not perform heartbreak as theater. Unlike the operatic force of Mario Lanza or the dramatic intensity often associated with Sinatra, Martin sings as if speaking to one person in an empty room. The intimacy feels almost intrusive. When he delivers the line about having only a photograph to tell his troubles to, it sounds less like a lyric and more like a confession.
“My father was the coolest man in the room, everyone knew that,” recalled Deana Martin in later interviews. “But at home he was gentle and sensitive. He liked quiet nights, dinner, movies. That side of him rarely showed in public.”
This private nature shaped the performance. Martin famously valued solitude. Where Sinatra chased company deep into the night, Martin often slipped out the back door after a show and returned home. Humor became his shield, charm his armor. In What’ll I Do, that armor cracks. His warm baritone, usually associated with romance and ease, turns hollow. The slight tremble on certain words does not sound practiced. It sounds human.
The song itself carries a long emotional lineage. Irving Berlin wrote it in 1923 during a period of personal romantic turmoil. Over the decades it was interpreted by artists ranging from Judy Garland to Linda Ronstadt. Few versions, however, capture the sense of quiet surrender found in Martin’s recording. There is no anger here, no bitterness. Only acceptance.
“Dean understood how to let silence do the work,” said arranger Nelson Riddle when reflecting on their collaborations. “His voice did not need to push. It needed space, and when you gave him that space, the emotion appeared naturally.”
The collaboration between Martin and Riddle is essential to the song’s impact. Riddle understood that Martin’s voice occupied a different emotional register than Sinatra’s. Where Sinatra cut through arrangements with sharp clarity, Martin blended into them. Riddle’s orchestration rises and falls gently, allowing the vocal to glide rather than dominate. In the chorus, when the orchestra briefly drops away and Martin asks who might be kissing the woman he loves, the absence of sound becomes devastating.
For years, some critics dismissed Dean Martin as merely a personality who happened to sing. They focused on the jokes, the slurred delivery, the cigarette smoke. Performances like What’ll I Do expose the flaw in that argument. Singing this quietly requires discipline, breath control, and emotional precision. It takes confidence to underplay heartbreak without slipping into sentimentality.
In today’s fast moving digital music culture, Martin’s recording feels like a message from another era. It reminds listeners that cool is not indifference. True cool lies in the courage to reveal oneself fully, to stand before a microphone with a broken heart and allow that fracture to be heard.Portable speakers
As the final violin note fades, the image of Dean Martin remains. He is smiling, but after these three minutes, that smile reads differently. It is no longer the grin of a man enjoying the party. It is the composed expression of someone holding himself together while the music continues to play.