He married his wife's best friend, had kids, walked away from a highly successful band to forge a solo career. He's written dozens of best-selling songs. A favorite old yellow-and-black striped sweater earned him the nickname "Stinger," later shortened to Sting.
Sting and his wife Trudie Styler, a filmmaker and actress, are yoga devotees who eat an all-natural diet. Last fall, they invited CBS News Sunday Morning Anchor Charles Osgood to spend a day at his home on Central Park West in New York City, to share an organic lunch with recipes from Trudie's cookbook.
Sting is a Renaissance man at the turn of the century, a musical time traveler, writing songs that are both eccentric and avant-garde.
The 48-year-old has made a career of doing exactly the opposite of what everyone expects him to do.
"While I like selling records, I also like to push the envelope a little bit," Sting explains.
Such pushing included sharing the stage with a wailing Algerian vocalist: high-risk behavior for a commercial artist, but the kind of musical innovation that has made Sting a superstar.
"I got very interested in whats called rai music, which is based in North Africa, Algeria and Morocco," he says.
"What interests me is that it's not pure ethnic music; it's a hybrid of North African, flamenco, French pop, Western pop music, reggae," he says. "I really feel at home in that kind of mix, because that's what I do. I like to mix things up and see what happens."
Where does the sophistication and sense of daring come from? He was 9 when his mother introduced him to a sensation named Elvis Presley.
"She would bring old 78s into the house. They were new at the time, and she put All Shook Up on, and I remember rolling on the floor with palpable excitement," he says.
So Sting picked up the bass guitar.
He recalls how his nickname came to be: "I used to play in a traditional jazz group when I was 16, with a group of much older guys," Sting says.
"And I used to wear these yellow and black sweaters," he says. "The guys, they thought I looked like a wasp, and they joked. They kept calling me Sting. That became my name. I just kept it."
After college, Sting worked a series of jobs but nothing held his attention.
"I dug ditches in the cold as well. I was [a] bus conductor. I worked in an office. I was a teacher," he says.
In fact, the head teacher was stunned when Sting announced his leaving.
"I went and said, 'Look, I want to hand in my notice at the end of the summer,' and she said, 'But what about your pension?' And I said 'I'm sorry; thats it. I'm gone,'" he explains.
Punk was the rage in 1977 when Sting went to London and joined a new band calle The Police. A now famous love song to a prostitute called "Roxanne" was the first hit song he wrote.
The Police were becoming the new kings of rock 'n' roll, with hit after hit. But at the height of it all, Sting was restless.
"I got the seven-year itch and decided to follow my instincts on my own against all logic," says Sting.
"Everyone was saying 'You're crazy; you're the biggest band in the world; you're making all this money. [But]I want to begin again. I want to carve out a niche for myself," he says.
His first solo effort took him back to his jazz roots, and his fans followed suit.
"I liked the spontaneity jazz musicians have. I like...their sense of danger," he says.
In the early 1980s, Sting's risk-taking spilled over into his personal life. An affair with a neighbor, Trudie Styler, brought an end to his marriage.
He filled the void with a manic work schedule, recording solo projects and trying new things.
He even starred briefly on Broadway. "I had a ball," Sting says.
Sting and Trudie had two children; they married and had two more. They try to keep their family out of the limelight, as they shuttle between houses - a duplex in Manhattan, a villa in Tuscany and an estate outside London, where they grow their own organic food. This is the subject of Trudie's cookbook, The Lake House Cookbook.
For Sting, however, there's organic food -- and then there's chocolate.
"You know what Sting will do, you see, he is this sort of ice creamholic," says Trudie.
"Chocolate," interjects her husband. "I love chocolate and ice cream."
"Chocolate and ice cream," Trudie continues. "And so he'll ask for it three times a day. And then when it's gone, he'll say, 'That's it. Don't buy anymore ice cream.' So then he'll go one day woefully to the fridge and say, 'There isn't any ice cream left...Okay. Well, just get it one last time.'"
Aside from playing the piano or guitar every day, another daily discipline of Sting's is yoga. He has been practicing it for 10 years.
"This is what I've learned, that breathing properly, your body is allowed to become more flexible. And then it becomes about meditations just by accident. You sit for hours and clean yourself out a little bit," he says.
These days, Sting's calendar is jammed as he tours with his latest record, Brand New Day. The release, another classic Sting mix of unexpected styles, is selling well.
"I still work hard every day. But one thing I learned at my most successful period is that I'd equated that with happiness as if they're the same thing," Sting explains. "Well, they're not, and that's an important lesson to learn."
One month after his 48th birthday, Sting has oly a short list of creative risks he's still willing to take: "Better songwriter, better singer, I think, better person. These are real ambitions for me," he explains.
Louis Pasteur wrote, "Chance favors the prepared mind." And by that measure, Sting is a man who has made his own luck.