When Rosemary Clooney set out to tackle the wistful bossa nova ballads of Antonio Carlos Jobim on her latest CD, "Brazil,'' it wasn't as easy as she thought it would be.

In fact, she admits it was the hardest music she ever had to learn. And that's really saying something coming from Clooney, who at 72 is regarded as one of the greatest jazz practitioners of American popular song.

She knows tough.

In the course of her lifetime, Clooney has suffered through the infidelities of her first husband, actor Jose Ferrer ... a marriage that later ended in divorce. She's been a mother five times over. She's lost friends and her lover. She's survived a nervous breakdown, which landed her in the hospital. And she's known what it's like to conquer the demons of prescription drug addiction, with the help of her family and friends, of course.

But with all the difficulties she has encountered in her life, Clooney has always managed to overcome those tough times. That's a little something she picked up in the early days of her career, when she was just another one of the boys to the group known as the Rat Pack.

Singing alongside her pals Bing Crosby and Frank Sinatra, way back, was tough, too.

"Bing and I could pick keys for each other because our voices were really in the same range,'' she says. "But Frank was really more of a tenor. So if there had to be someone making a concession because of the song, it would have to be a dramatic concession, and I hated that, because we had to change the gender or something in the lyric of the song just because I couldn't sing it as high as it obviously went for Frank to be comfortable.''

But when it comes to Brazilian music, as she came to learn during the making of the CD "Brazil,'' the bossa nova is much different from the American classics that Clooney ... who will be performing with Michael Feinstein and the Los Angeles Philharmonic on Friday and Saturday at the Hollywood Bowl ... has spent nearly a lifetime singing.

"The time signatures are so difficult,'' Clooney says by phone from her home in Los Angeles. "Also, it can be very rangy. The musical interludes may not be as simple as the ones that I'm used to recording, even with somebody like Cole Porter, who didn't consider the human voice at all when he wrote melodies.''

But with the help of guitarist John Pizzarelli, whom she lovingly refers to as Johnny, and singer Diana Krall, who duets with the legendary crooner on "Boy From Ipanema,'' it's not surprising that Clooney manages to pull it all together in much the same way as she has her life.

After her nervous breakdown, Clooney worked her way back to the concert stage, playing any gig she could get. Some times only a handful of people would show. But that's not true anymore.

Clooney just got back from San Francisco, where she performed with the San Francisco Symphony. And Friday, she does a show of popular American songs from the last 100 years at the Hollywood Bowl.

Later this year, she even plans to do a tour in support of her album "Brazil.'' But she's still working out all the details.

Clooney says no matter what, she wants to bring along Pizzarelli. He is one of the two people, after all, who helped get her through one of the toughest lessons in her singing life ... performing bossa nova on her first- ever Brazilian album the way it was intended to be performed.

The result is an album of songs ... "Corcovado (Quiet Nights),'' "Desafinado'' and "Waters Of March'' ... from a country that still pulses in her memory.

"I wasn't there very long,'' Clooney says. "But it was so indelible, the memory of it was so bright, and it didn't fade through the years.

Clooney, who did a three-week concert tour of Brazil in 1968, recalls the country as a place filled with beautiful people, music and lots of color. Since she traveled the country by car ... she hates flying ... Clooney got to experience Brazil firsthand.

"The people are beautiful, of course,'' she says. "But the music is constant. It's in every little place that you go.

"If there's a three-stool cantina, they've got a jazz group with five rhythm instruments. The whole place seems to be set to music. It was just an enormously moving experience for me.''

In the liner notes of "Brazil,'' Clooney recalls her memory of looking out of her hotel room and seeing the mountains and sea bathed in a lavender light.

"I was just terribly impressed with it,'' she says. "And it's funny because I want to go back, but I don't want to go back. I don't want to spoil the memory of it. It's so perfect. Perhaps, it's too perfect.''

c.2000 Los Angeles Daily News