Frank Sinatra Gave His Daughter Lucrative Advice When She Posed for Playboy

In the mid-1990s, Frank Sinatra’s daughter Nancy planned to release new music for the first time in years. The comeback album only came to be when she received money for posing on the cover of Playboy Magazine. Beforehand, she asked her father what he thought about the situation. He offered her surprisingly helpful advice about the deal.

A black and white photo of Nancy Sinatra and Frank Sinatra. He holds a drink and a cigarette.
Frank Sinatra and Nancy Sinatra | Earl Leaf/Michael Ochs Archives/Getty Images

Frank Sinatra’s daughter Nancy also went into the music industry

Nancy Sinatra followed in her father’s footsteps. Like Sinatra, she began pursuing music at an early age, explaining that she gave her first performance as a teenager.

“I was 18. I did The Ed Sullivan Show.,” she told Rolling Stone. “And I did a Shirley Temple song in a big straw hat. I wore overalls. My hair was very dark brunette. It was just awful. It was live TV, in front of millions of people. I must have been out of my mind.”

Her musical style departed from her father’s, however. She partnered with Lee Hazlewood and blended rock, pop, and country to a twanging, psychedelic effect. Still, she learned a lot about performing from Sinatra.

“He was a genius. He enjoyed it,” she said, adding, “He made the audience feel at home. The biggest thing I learned was consistency. He was meticulous about how he dressed. His shoes were always spotless. He was so professional. “

He offered her advice before she posed for Playboy

Though she took a step back from music, she put out a comeback album, One More Time, in 1995. In order to finance it, she decided to pose on the cover of Playboy.

“There would not have been a record were it not for Playboy,” she told the Independent. “I really was determined to make another album and I didn’t have any money to do it. And when I asked Hugh Hefner if I could do a pictorial for money, he said of course. We were old friends from way back.”

She was stressed about posing on the cover and went to Sinatra for advice. 

“I was a nervous wreck,” she explained. “I was so embarrassed. But I was determined to get the money for this album. They offered me $50,000 and I told my dad about it. I said, ‘What do you think?’ And he said, ‘double it.'”

She went back to Hefner, and he agreed to the larger sum.

Nancy Sinatra said Frank Sinatra gave a lot of good advice

Nancy explained that she often went to her father for advice, and he gave valuable information. She shared the best advice he ever gave her.

“My dad was pretty good at advice,” she said. “And he gave me the advice about owning my own masters. He started Reprise, his label, because he was unable to own his masters at Capitol Records. And he made it possible for all the artists on Reprise to own their own masters after a certain period of time. I heard Taylor Swift’s masters were sold again. That’s a shame. I would say to young people: Don’t despair, hold on to your dreams, and don’t let anybody else own them.”

RELATED: Stevie Nicks Gave Frank Sinatra’s Daughter the ‘Cold Shoulder’: ‘That Was Painful for Me’