Keali‘i was born and raised on Maui, growing up in Lahaina and spending weekends and summers at his grandmother's house in Pa‘ia on the windward side of the island. His passion for the language and culture of Hawai‘i led him to become the founding director for Pünana Leo O Maui, the Hawaiian language immersion school. He also founded his own hula school, Halau Ke`alaokamaile, in 1980 and has won numerous awards over the years. Keali`i is also recognized as an accomplished chanter.

In 1994 he independently produced and released a collection of Hawaiian traditional and contemporary songs and chants entitled "Kawaipunahele.” His subsequent music releases, "Lei Hali`a" (1995), "E O Mai" (1997), "Melelana" (1999), and “Ke‘alaokamaile (2003) have cemented his place in the Hawaiian music industry. All told, he has been awarded 19 Na Hoku Hanohano Awards, and his consistent placement in Billboard Magazine's World Music and Heatseeker Charts has garnered him international attention.

Keali`i has opened concerts for Bonnie Raitt, LeAnn Rimes, Celine Dion and Sting, and has played such diverse venues as Carnegie Hall and the Hollywood Bowl, and consistently sells out concerts from Honoka‘a to Honolulu, Seattle to San Diego, Okinawa to Osaka.

Keali‘i retains his initial goal of presenting new compositions in the Hawaiian language for hula students, and works to dispel long-held stereotypes of Hawai‘i’s living culture and her indigenous people.

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