In 1972, Kamakahi became a member of a Hawaiian music group known as Na Leo O Nu'uanu. His first recording with Na Leo O Nu'uanu was the album ''Ia 'Oe E Ka La Volume 1'', released on the Nakahili Productions label with Palani Vaughan. It was the first of a series of albums based on the life of King
David Kalakaua. The second recording of the group, released 1974, was recorded live at a music festival in Waimea, Hawaii, called The Waimea Music Festival. The festival featured many of Hawaii's popular entertainers of the time including
Gabby Pahinui,
Fred Punahoa,
The Sunday Manoa and
Genoa Keawe. It was his tenure with
Eddie Kamae and the
Sons of Hawaii (1974–95) after replacing
Gabby Pahinui that led Kamakahi to become one of Hawaii's most prolific songwriters in the
Hawaiian language, composing around 500 songs. In 1974, Kamakahi recorded with the Sons of Hawaii for the
National Geographic Society's
Music of the World series. This was the beginning of seven albums under the Hawaii Sons label and the recording of many of Kamakahi's music compositions. In 1978 he became a member of the
American Society of Composers, Authors, and Publishers and created Naukilo Publishing Company, a music publishing firm. From 1988 until 2004, he continued to work with Kamae, recording soundtracks for several Hawaiian documentary films:
LI‘A: The Legacy of a Hawaiian Man,
Listen to the Forest,
The Hawaiian Way: The Art and Tradition of Slack Key Music,
Words, Earth & Aloha: The Source of Hawaiian Music,
Luther Kahekili Makekau: A One Kine Hawaiian Man,
Hawaiian Voices: Bridging Past to Present, ''Sons of Hawai'i: A Sound, A Band, A Legend
, Hawaiian Son: The Life and Music of Eddie Kamae
and Keepers of the Flame: The Legacy of Three Hawaiian Women'', all produced by Eddie and Myrna Kamae as part of the Hawaiian Legacy Foundation series. Kamakahi launched his solo career in 1996, releasing his first slack key guitar CD ''Pua'ena
, (Glow Brightly
) co-produced by Howard Johnston and pianist George Winston, under Dancing Cat Records. In 1998 he released his second slack key guitar CD for Dancing Cat Records together with son David Kamakahi on the ukulele. The CD was called Ohana
(Family
). It was soon followed by another Dancing Cat Records release, Hui Aloha
(Play Together''), featuring both Dennis and David Kamakahi, George Kuo, and Martin Pahinui. In 2003, under his own recording label, Dennis Kamakahi Productions, he released a second album with son David,
The Gift of Music - From Father to Son. The CD included narration between each song to explain its meaning. In 2003, both Kamakahi and David became involved with
Disneytoon Studios to provide vocals and instrumentals for the animated film
Lilo & Stitch 2: Stitch Has a Glitch (2005) as well as its soundtrack, ''Disney's Lilo & Stitch Island Favorites''. It was also at this time that Kamakahi became a member of the
Screen Actors Guild. Kamakahi produced an album featuring his son in 2004 entitled ''Pa'ani
(Play''). The CD was the first solo ukulele effort of David and garnered a
Na Hoku Hanohano Award from the
Hawaii Academy of Recording Arts for Contemporary Album of the Year in 2005. At that same Award Ceremony, Kamakahi was honored with the Na Hoku Hanohano Kiho'alu Award (Slack Key Award) by the Hawaii Academy of Recording Arts. At the
49th Grammy Awards in
Los Angeles, California, on February 11, 2007, Kamakahi received his first
Grammy Award for Best Hawaiian Album for the slack key guitar compilation CD
Legends of Hawaiian Slack Key Guitar, part of the recorded live concerts at
Kapalua, Maui, at the Ritz Carlton Hotel. Kamakahi received his second Grammy in the Hawaiian Music Category in 2008 at the
50th Grammy Awards in Los Angeles for the slack key guitar compilation CD
Treasures of Hawaiian Slack Key Guitar, part of the second recorded live concert series at the Napilikai Resort Hotel in Kapalua, Maui. He also joined the
Music Teachers National Association that year to continue the teaching and advancement of music composition to students. Kamakahi was nominated for a third Grammy in 2009 at the
51st Grammy Awards with the slack key compilation CD
The Spirit of Hawaiian Slack Key Guitar, a third recorded live series at the Napilikai Resort Hotel in Kapalua, Maui. The CD did not win the award, but Kamakahi did receive his first gold Grammy Nominee medal as a record producer. Kamakahi was nominated a fourth time for a Grammy Award for his slack key compilation CD
The Masters of Hawaiian Slack Key Guitar Volume 2 - Live in Maui and won his third Grammy for Best Hawaiian Music Album at the
52nd Grammy Awards on January 31, 2010. In 2009, Kamakahi was awarded the Lifetime Achievement Award from the
Hawaii Academy of Recording Arts as a member of the Sons of Hawaii and inducted into the Hawaiian Music Hall Of Fame. Until his death, Kamakahi continued to perform in live concerts in Hawaii and abroad, and teach Hawaiian slack key guitar, the history of Hawaiian songs and their meaning, and songwriting workshops in both Hawaii and the U.S. mainland. He died of
lung cancer in 2014. ==Awards and recognitions==