HOT FOR THE COOL

Anew era is beginning in the career of Frank Sinatra even if the Chairman of the Board isn’t here to participate.

The iconic singer died May 14, 1998, and the 10th anniversary is being marked with a flurry of activity, including a new U.S. postage stamp with his likeness, lavish new CD and DVD collections, a major revival of his films on television and high-profile media appearances by his children.

This surge in all things Sinatra is more than just a fleeting commemoration, however -- it’s more like the beginning of a corporate brand roll-out.

Late last year, the Sinatra heirs signed a pact with Warner Music Group Corp. that will bring Ol’ Blue Eyes back in a big way, not just as a digitally resurrected entertainer but also as an advertising pitchman and, potentially, the name on the marquee of a feature film, a Broadway show and a casino and resort.

“Those are some of the things that have been discussed. We will see,” said Tina Sinatra, the singer’s younger daughter and the heir most involved in the estate’s day-to-day enterprises. “The amazing thing is how untapped all of it is. By design we have done very little, particularly once he died.”

What Sinatra offers to any venture is that most elusive of auras: eternal cool. Like Elvis Presley, James Dean or Marilyn Monroe, Sinatra’s image has compass-point clarity in pop culture despite the passage of time. For advertisers, he could be an especially potent signifier of sophisticated standards and rakish elegance, and Warner executives sound like gamblers with winning hands when they talk about it.

“There’s a famous old saying that, ‘It’s Frank Sinatra’s world, we just live in it,’ and that’s kind of how we feel around here now,” said Jimmy Edwards, one of the executives at Warner’s Rhino Records who will be leading the day-to-day operations of Frank Sinatra Enterprises LLC. “Frank opens the door to a very exclusive club. . . . He crosses so many zones too; he’s working-class, but he also runs around with the country-club set.”

The venture, funded and operated by Warner, has two major advertising deals in place and is close on two others. Dozens of other overtures have been turned down. Edwards and fellow executive Gregg Goldman declined to say what products will soon have Sinatra as an expensive salesman, but Goldman said the accounts speak to Sinatra’s passions, “gaming, fine dining, the finest apparel and luxury.”

The company’s partnership in Frank Sinatra Enterprises is a departure from the traditional core business of the recording company but, with the gutting of CD sales in recent years, major labels and other players in the sector are looking for new business models.

In recent months, for instance, Live Nation signed deals of $100 million or more with Jay-Z, U2 and Madonna to bundle an assortment of their revenue streams and ventures, both on stage and off. Faced with a diffused marketplace, companies are trying to scoop up key superstars and bottle up all their moneymaking power.

Financial terms of the Sinatra deal have not been disclosed. Edwards said the plan is to be intensely selective. Next week, the company will relaunch www.sinatra.com and begin a methodical mining of “a Sinatra archive that is enormous.” A major documentary project is also being pursued.

“The opportunities for this artist,” he said, “are unparalleled.”

But there’s also a danger of saturation or, worse, making a crass misstep. Many devotees of Fred Astaire, for example, recoiled a decade ago when the late star was digitally made to dance with a Dirt Devil vacuum cleaner. When you have a singer who made “My Way” a musical life statement, you don’t want to hit a sour note.

“There is a lot of interest, and the hard part is deciding what is right and what is wrong,” Tina Sinatra said. “But people remain fascinated by Dad. The truth is that his image and his cachet has sustained and perpetuated him just as much as his incredible talent. He is handed from one generation to the next. Things that would suit him and his lifestyle make sense to me. But now I’m in a corporation, it’s not just me.”

Some apprehensions

Sitting in her sunny office on Olympic Boulevard, Tina Sinatra was plainly proud while discussing the grand plans that the Warner deal will set in motion, but there was also some apprehension in her voice. She was particularly enthusiastic about discussions of a Sinatra film directed by Martin Scorsese -- “He’s really the only one to do it, isn’t he?” -- but less certain about the proposals she’s heard that would put her father’s name on the front of a menu.

“I’ve dragged my feet about a restaurant,” the 59-year-old said. “The dreaded term ‘chain of restaurants.’ A casino would interest me a lot. That’s his environment. It would have to be top-end. As would a Sinatra hotel. A casino, that’s on the nose, but it’s a big undertaking. I would love to see a dress code enforced at a Vegas casino, but I don’t know that it could work. Las Vegas is so competitive. We’re thinking beyond Las Vegas too. It’s a big world out there.”

Tina Sinatra and attorney Robert A. Finkelstein have been the family’s main gatekeepers on licensing matters since the 1980s, when her father was still touring. But the job became too large and complicated for a small-team approach. With Warner’s investment comes the opportunity for major windfalls but also the surrender of some control.

Tina Sinatra and Finkelstein represent the two family votes on the board of Frank Sinatra Enterprises. Warner has two also: company Chairman and Chief Executive Edgar Bronfman Jr. (who led the investor group that bought the company from Time Warner in late 2003 for $2.6 billion) and Scott Pascucci, president of Warner’s Rhino Entertainment, a brand known for meticulous archival collections and a safari-like approach to music history. A fifth, tie-breaking vote is held by former Capitol Records President Hale Milgrim, a respected industry veteran selected by both sides, but Edwards said the goal is unanimity.

The Sinatra family itself has some considerable divisions. Tina has feuded with her father’s fourth and final wife, Barbara. Frank Sinatra left control of his estate’s business to his children -- Nancy, Frank Jr. and Tina, all from his first marriage. The children are not completely on the same page, either. Nancy Sinatra, 67, is against a feature film, even if Oscar-winner Scorsese fulfills his longtime goal of directing it. She fears it would dwell on the negative and ugly moments of her father’s complicated life. She prefers an eight- to 10-hour documentary, which needs to be “very, very precise.” Nancy also said her father “never wanted his image to be on an ashtray” and that any advertising “must be equal to his excellence, which is not easy to do.”

Frank Sinatra Jr., meanwhile, is busy touring and performing with the songbook and arrangements he inherited from his father. The 64-year-old growled a bit when asked about a feature film or a casino. “This is the first I’m hearing about a lot of these things,” he said. “I’m the last person to hear about these things. . . . I’m not party to all those decisions, not like I would like. That’s the way it came down.”

His legacy

After decades in the spotlight, Frank Sinatra performed in front of a live audience for the last time in February 1995. The final song was “The Best Is Yet to Come,” but his health made a liar of the lyrics. Two years later, his body giving out, he sent daughter Nancy to accept a Congressional Gold Medal in his name.

In his final months, staring into the twilight, the music titan wondered how he would be remembered. During one late-night conversation, Tina Sinatra remembered, he said his legacy might be as fragile as vintage vinyl.

“He said he thought it depended on who held him close to their heart in their record collection and if they’d pass it all on,” she recalled. “He wasn’t certain. There was no arrogance. There was doubt in his voice.”

This month, Sinatra’s voice will be everywhere and his legacy difficult to ignore.

Tina Sinatra and Frank Jr. will appear on “The Today Show” on Tuesday to talk about the new postage stamp, the same day as tie-in events in New York, Las Vegas and Hoboken, N.J., where the most famous saloon singer of them all was born in 1915. Also on Tuesday, Warner’s Reprise Records releases “Nothing But the Best,” a new survey of his signature songs.

All three Sinatra children have taped introductions and interviews for Turner Classic Movies, which will be airing about four dozen Sinatra films this month on Wednesdays and Sundays. Warner Home Video has four new lavish DVD collections headed to stores with 17 Sinatra films in all.

Nancy Sinatra said that the voice of her father has never really gone away and that the fascination with it represents curiosity about the American journey. It’s all there, she said: showbiz and politics, fame and heartbreak, talent and style. “His life was the story of the 20th century,” she said. “He went from megaphones to fiber optics, and he was the biggest star all the way. No one else has done that.”

Tina Sinatra said the Warner deal was needed because “none of us are getting any younger, and the work is important.” In the 1980s, she and Finkelstein started dealing with counterfeit and unauthorized products by getting in the business of licensing Sinatra products. She took her father different proposals -- bobble-head dolls and hats, Franklin Mint souvenir coins and music boxes -- and some made him chuckle, while others brought one of his famous scowls. Back then it was small steps; now it’s a giant leap of faith.

“We have been a little cottage industry until now, just holding on and controlling what we can handle ourselves. It’s a new era coming,” she said. “It’s here now, really, it’s all going to start happening pretty fast. The funny thing is a lot of it, it just makes me miss my father even more.”

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geoff.boucher@latimes.com