Come Fly
With Him
THURSDAY, MAY 22, 1998 -- The clock radio clicked on in the wee small hours of the morning on May 15. Fat Boy the Frequent Flyer opened his eyes and he knew something was wrong.

He wasn't in a hotel. This was home. His bed. His sheets. What was wrong?

Then Fat Boy the Frequent Flyer figured it out. There was music coming from the radio. That was wrong. Why was the all-news station playing music?

Fat Boy lay there for a second and then he understood. It was a Sinatra song. Sinatra music on the all-news station could mean only one thing: Sinatra was dead.

Fat Boy fumbled for his glasses and hoisted himself up. The music stopped and the news anchor went through the facts. Fat Boy half listened: 82-year-old legend... heart attack... Rat Pack... most influential entertainer of the 20th Century...

Fat Boy got up, rubbed the sleep out of his eyes, and shuffled toward the CDs by the radio. He flipped past Only the Lonely and Come Dance With Me. He stopped at his favorite, the Sinatra/Jobim album, and smiled. Then he kept flipping. Sinatra with Duke Ellington. Nope. Sinatra at the Sands. Nope. Sinatra and Count Basie. Nope. Nice and Easy. Nope.

When he found it, Fat Boy looked at the cover and shook his head in amazement. Fat Boy always shook his head in amazement when he saw the cover of Come Fly With Me.

Over coffee, Fat Boy the Frequent Flyer pulled the CD out of the pocket of his robe and stared at Come Fly With Me for the millionth time in his life. Vivid blue sky. The perfectly articulated TWA Lockheed Constellation over Sinatra's right shoulder. The red-striped loading bridge over his left shoulder. The way he wore his fedora with a dip in the brim. The perfectly knotted tie. The gold cufflink in Sinatra's starched white cuff.

All his traveling life, Fat Boy the Frequent Flyer thought, Come Fly With Me was there. What was it that guy at the bar in Hartsfield had called it 20 years ago? Oh, yeah, the soundtrack of the road.

Sitting at the bar one stormy summer night in Atlanta, waiting out the delay, Fat Boy found himself talking Sinatra with another stranded flyer.

"Every frequent flyer in the world wants to be Frank Sinatra from Come Fly With Me," the guy had said. "We all want to wear that hat, we all want to fly around and make believe it's a swinging world. I used to think frequent flying was about 'exotic booze in a bar in far Bombay' and a 'one-man band in llama land who'll toot his flute for you.' "

"I dunno," said Fat Boy. "It was a good album and all, but..."

"Are you saying you never wanted to be Sinatra?" the guy asked.

"You kidding?" said Fat Boy. "When I grew up, I thought I'd move to Manhattan and live in an apartment just like Sinatra's from Come Blow Your Horn. I live and breathe Sinatra. But I never thought Come Fly With Me was all that big a deal."

"I'm telling you," the guy said, "it's the soundtrack of the road. In every frequent flyer's head, we hear Come Fly With Me every time we fly."

Over the years, Fat Boy learned that the guy from the bar in Atlanta was right. Wherever Fat Boy went, he seemed to find frequent flyers with a Come Fly With Me fixation.

The business traveler in London who had an artist recreate the cover of Come Fly With Me with him instead of Sinatra wearing the hat and posing in front of the Constellation. The frequent-flying salesman from Zurich who took his autographed copy of Come Fly With Me on all his business trips. And the woman in San Francisco who claimed she's visited all the spots on Come Fly With Me--from the Isle of Capri and moonlit Vermont to Brazil and Blue Hawaii--in the exact order the songs appeared on the album.

"It is all about timing," a retired airline executive once told Fat Boy. "Come Fly With Me came out in 1957, two years before the first jets went into service. The sophisticated [Billy May] arrangements, the hip Sinatra vocals, the travel theme of the album, they became identified with the jet era. In the late 1950s, Sinatra and jets were the epitome of cool. It was hip to be a traveler and we all thought we were Sinatra."

Later in the day, Fat Boy the Frequent Flyer packed a bag, his briefcase and his laptop, then threw them all in his Jeep. No jets today, he thought, just a three-hour drive. But he grabbed his copy of Come Fly With Me and tossed it in the front seat.

"One more for the road," he said out loud.

Then Fat Boy the Frequent Flyer smiled, hummed a couple of bars of Come Fly With Me and drove away on the day Sinatra died.

This column originally appeared at