In 1957, Frank Sinatra conducted an album for Peggy Lee, called "The Man I Love". Peggy Lee: “The album was totally his concept. He brought me a long list of great songs from which to choose. Then Frank hired Nelson Riddle to write those lovely arrangements and Frank conducted them - a marvelously sensitive conductor, as one would expect. He designed and supervised the cover. He is a producer who thinks of everything - even putting menthol in my eyes so I'd have a misty look in the cover photograph.”

Sinatra helped Lee again, even more significantly, when she became seriously ill later in life. Tony Oppedisano: “Peggy wasn't in the best of health one morning when she had to fly out to New York on business. Things only got worse after her arrival, and she was soon hospitalized, gravely ill. Frank kept tabs on her from LA. He'd been worried about her making the trip when her health was so fragile. When he found out she was in the hospital, he talked to her doctor directly."

‘So what's the deal?’ Frank asked him.

The doctor told him, ‘Well, I'm worried about her state of mind. She's very depressed because she's not home in her familiar environment.’

The doctor explained that Peggy was in a bad way – in strange surroundings, away from her loved ones, seriously ill, and desperately homesick. Frank offered to fly her home on his plane, but the doctor said she wouldn't survive the trip.

‘We've discussed that, but I've explained to her that it isn't safe. She has to be in a hospital environment right now.’

Frank said, ‘Okay.’

He made a few calls, and within twenty-four hours, he'd had his private plane completely reconfigured as a hospital plane, including the necessary equipment and medical personnel. He contacted Peggy's medical team and sent the plane to New York. An ambulance took Peggy's medical team and sent the plane to New York. An ambulance took Peggy from the hospital to Teterboro Airport. There, they put her on Frank's jet with a doctor and a couple of nurses and flew her home. Meanwhile, Frank had her home set up like a hospital room and made arrangements for 24/7 medical care. When the plane landed in LA, it was met with an ambulance and nurses, who brought Peggy home. It must have cost a small fortune, but Frank brushed away any mention of the money. The world didn't know about it, but Peggy and her doctor knew that Frank had saved her life.”

Peggy Lee sang about this at the Ella Awards in 1990 with special lyrics on the melody of “The Man I Love.”

Frank Sinatra about Peggy Lee: “Peggy and I met early in our careers when we both started out in New York, and have been great friends ever since. Her wonderful talent should be studied by all vocalists; her regal presence is pure elegance and charm.”

Peggy Lee about Frank Sinatra: “There are very few men in our business who have affected me so deeply I can't express myself, and Frank is one of them.”

Frank Sinatra was dining at an upscale restaurant in Los Angeles when he noticed a young waiter looking distressed. Sinatra, known for his sharp eye and ability to read people, observed the waiter speaking quietly with another staff member about something clearly troubling him. The singer, always curious about the lives of those around him, called the young man over and casually asked: “What’s on your mind, kid?”

Hesitant at first, the waiter admitted he was struggling to pay for his college tuition. His dream was to finish school and build a better future, but mounting costs had made it nearly impossible. He had taken extra shifts at the restaurant, working long hours just to stay afloat, yet it wasn’t enough. Sinatra listened intently, nodding as the young man explained his situation.

After a brief pause, Sinatra pulled out his checkbook and asked:“How much do you owe?” The waiter, thinking it was just a friendly question, hesitated before giving him the number. Without another word, Sinatra wrote a check covering the entire amount. When the stunned waiter tried to refuse or offer some form of repayment, Sinatra simply slid the check across the table and said: “Just do something good for someone else someday.”

The staff at the restaurant, accustomed to serving celebrities, had seen stars come and go, but this moment was different. Sinatra wasn’t looking for attention or public praise - he never did when it came to his charitable acts. He simply saw a kid in need and did what he could to help. The story of this moment spread among those who worked in the restaurant industry, becoming another example of Sinatra’s legendary generosity.

Sinatra’s reputation as a tough, no-nonsense personality often overshadowed his deep sense of loyalty and kindness. Those in his inner circle knew he had a soft spot for hardworking people trying to make something of themselves. He had spent his own youth in Hoboken, New Jersey, watching his parents struggle to make ends meet. Though he later achieved massive fame with hits like "Strangers in the Night" and "My Way," he never forgot the value of lending a hand to someone who needed it.

This wasn’t an isolated incident. Throughout his life, Sinatra privately helped countless people, from struggling musicians to strangers he met by chance. On another occasion, he reportedly left a $2,000 tip for a cab driver who had driven him across town late at night. Once, he paid off a struggling friend’s mortgage without being asked. He even sent money anonymously to hospital patients and war veterans who had no idea where the funds came from.

The young waiter who received Sinatra’s generosity never forgot what had happened that night. He graduated from college, pursued his dreams, and carried the lesson with him: a simple act of kindness could change a life. Years later, when he was in a position to help others, he followed Sinatra’s advice and paid it forward.