Led Kaapana grew up in a family of musicians in Kalapana, in the southernmost district of Hawaii Island. His teachers included his mother, Mama Tina Kaapana, from whom he learned to sing leo ki'eki'e (Hawaiian falsetto singing), and his uncle, Fred Punahoa. "We didn't have electricity, not television, not even much radio," says Kaapana. "So we entertained ourselves. You could go to any house and everybody was playing music."
Throughout his career, Ledward has dedicated himself to perpetuating the traditional style and repertoire of his home, beginning in his teens when Led, his twin brother Nedward, and cousin Dennis Pavao formed the musical group Hui ‘Ohana. The group produced 14 best-selling albums, made hundreds of live appearances, and became a key figure in the resurgence of traditional Hawaiian culture and music during the 1970s. Launching a solo career in 1983, Kaapana has continued to garner acclaim for his improvisational melodies and falsetto vocals. His 1983 solo album Lima Wela received the prestigious Nā Hōkū Hanohano (Hawai‘i’s “Grammy”) award as "Best Instrumental Album"; the honor was repeated in 2000 with his Black Sand CD.
Led also formed the trio I Kona, releasing six albums from 1978-1998, including Jus' Press, which received a Nā Hōkū Hanohano award. He toured with the National Council of Traditional Arts program, "Masters Of The Steel String Guitar", from 1990 to 1992. Kaapana earned Grammy nominations in 2006, 2007, and 2009, and was featured on three of George Kahumoku’s four Grammy-winning compilations from the renowned Slack Key Show on Maui. In 2008, Kaapana formed his own recording company, Jus' Press Productions, and released Force of Nature with 12-string virtuoso Mike Kaawa, earning a Grammy nomination and Favorite Entertainer Awards at the 2009 Nā Hōkū Hanohano Awards.
Kaapana has worked with Nashville musicians Dolly Parton and Chet Atkins (whom he cites as an early influence) and collaborated with Alison Krauss, Jerry Douglas, and other bluegrass musicians for Waltz of the Wind. In addition, Kaapana has recorded with numerous renowned Hawai‘i musicians, including NEA National Heritage Fellows Aunty Genoa Keawe, the Ho'opi'i Brothers, and Barney Isaacs.
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