Where Trouble Melts Like Lemon Drops

The story of how Bruddah IZ recorded "Over the Rainbow"

In the early 2000s I grew obsessed with the history of Hawaiian music, from Gabby Pahinui to Kui Lee, Sunday Manoa, and Israel Kamakawiwo’ole. I began to work on a music biography about Israel, and almost sold this proposal twice, but both publishers insisted a music CD be pasted into the back of the book. Permission was denied from the record label because they were committed to earning money for Israel’s family (he passed away in 1997). In the age of music streaming, this CD book packaging concept now sounds ridiculous, but so it goes. This excerpt was the opening chapter, which originally appeared in the San Francisco Chronicle in 2005.

Honolulu, 1988, two a.m. Music producer Jon de Mello is sleeping when the phone rings. It’s Israel, one of the artists he represents for his Mountain Apple record label. And Israel is wide awake. He often has problems at night because his weight, upwards of 700 pounds, forces him to sleep while hooked up to an oxygen tank. He tells de Mello he wants to record, right now.

“You got transportation?” asks de Mello. It’s difficult for Israel to move around, he needs a few people to help him get dressed, get in and out of places. The studio is about 15 minutes away.

“Yeah,” says Israel. “My guys are here.” “Get in the car,” says de Mello. “I’ll meet you over there.” In the car, de Mello wonders what he wants to record. They’ve been discussing a bunch of possibles from a songbook. But it’s Israel, you never really know for sure what he’s going to do. A traditional Hawai’ian hula. A John Denver song. A theme from a TV show. Could be anything.

A young engineer named Milan Bertosa sits in his recording studio, waiting. He was planning to go home, until some Hawai’ian guy with a lot of letters in his name called up and wanted to record something right away. It’s late, Bertosa is tired, but the voice was insistent, saying he only needed half an hour. A knock at the door, and there stands an unimaginable sight. De Mello, whom Bertosa recognizes, stands about five foot two and 100 pounds. Next to him, the largest man he’s ever seen, a gargantuan six-foot-six Hawai’ian carrying a ukulele. De Mello introduces the two, they get Israel situated in a chair, and Bertosa starts rolling tape.

Israel leans into the microphone, says: “’kay, this one’s for Gabby,” and begins gently strumming the uke. His beautiful voice comes in, a lilting “Oooooo,” then slips into the opening words of “Over the Rainbow,” from The Wizard of Oz. Bertosa listens behind the glass, and within the first few bars knows it’s something very special. He spends most of his time recording lousy dance music. This is otherworldly. An incredibly fat man, elegantly caressing a Hollywood show tune, breaking it down to its roots, so sad and poignant, yet full of hope and possibility. Halfway through the tune, Israel spirals off into “What a Wonderful World,” the George David Weiss/Bob Thiele hit made famous by Louis Armstrong, then melts back into “Over the Rainbow.” He flubs a lyric, and tosses in a new chord change, but it doesn’t matter. It feels seamless, chilling. Israel plays five songs in a row, then turns to de Mello and says, “I’m tired and I’m going home.” “Gets up and walks out,” says de Mello. “Ukulele and a vocal, one take. Over.” Israel never played the song again.

When Israel and de Mello began piecing together his 1993 album Facing Future, they added the demo tape of “Over the Rainbow.” Upon release the song took on a life of its own. The familiar melody played in hotels and on rental car radios, in restaurants and bars. Many were moved to tears. If it didn’t give you “chicken skin,” you were legally dead. The song resonated even more for locals. Some heard its kaona, or hidden subtext, to reflect the sadness Hawai’i felt about having its lands illegally annexed by the United States in 1898. Those who had seen him in concert knew he ended each show with the words, “My name is Israel Kamakawiwo’ole, I am Hawai’ian.” Israel was one of only 1, 500 full-blooded Hawai’ians left in the world. He was pure, and so was the recording. It bounced around the islands for the next few years.

And then one afternoon, Santa Monica KCRW radio host Chris Douridas cued up “Over the Rainbow” as part of the program “Morning Becomes Eclectic,” to cheer up listeners on a rainy day. After it faded out, Douridas announced the 800 phone number on the back of the Facing Future CD. In two days, Mountain Apple received over 2,000 calls from southern California, people crying and asking about the music, many of them stuck on the freeway when they heard it.

Movie producer Martin Brest bought the rights for use in his 1998 film, Meet Joe Black. As the end credits rolled, movie audiences stayed in their seats to listen to “Over the Rainbow.” One of America’s most recognizable melodies, first made popular by Judy Garland, the tune had always embodied optimism, depicting a world where dreams really do come true. Israel’s version was something else entirely: haunting and delicate, stripped down to a lone voice and a ukulele, an unexpected minor chord contrasting, almost unconsciously, against the happy lyrics of wishing upon a star. After the film’s premiere in Hawai’i, people were sobbing in the theater.

Producers bought the very same song for Finding Forrester, Made, The Big Bounce, and 50 First Dates, for episodes of ER, Providence, Charmed, and Party of Five. It aired in an eToys ad during the Super Bowl, and then commercials throughout Japan, Europe, Australia, New Zealand. Although most listeners couldn’t remember the name of the artist, it didn’t matter. The music was most important, that raw, perfect-pitch voice that hit people right in the heart, touched their emotional core, reminded them how fragile life can be. You heard it once, you never forgot it.

“Rainbow” came to personify Hawai’i to the outside world. Celebrities publicly announced their love of Israel’s music: novelists, actors, directors, baseball players, sumo wrestlers. Bruddah IZ was the state’s first artist in history to have an album certified gold. Posters and calendars of his face decorated record stores around the world. “Over the Rainbow” became the No. 1 bestselling song downloaded from the World Music section of iTunes. Israel had produced the most recognizable and beloved Hawai’ian song in 50 years. And he didn’t live to see any of it.