When Henry Kapono steps up to the mic at Duke’s on Waikiki Beach, the crowd goes wild. Dancers groove at the foot of the outdoor stage while guests seated at tables nod their heads and raise their beers to the music.

For more than 30 years, this has been Kapono’s spot on Sunday afternoons. Just before sunset, the famed singer-songwriter will play a two-hour set of original songs, rock covers, and classics from his time with Cecilio & Kapono, the local musical group that gave Kapono his first major break in the 1970s.

“C&K was magic. We played together really well and there was a positive energy that we shared musically,” says Kapono. “There’s that energy at Duke’s too, the vibe is so good. Diamond Head, Waikiki, blue skies, sunshine, you know?”

Jimmy Buffett agreed — the “Margaritaville” singer first met Kapono at Duke’s on a Sunday in the mid-2000s. They sang and played “Brown Eyed Girl” and “Margaritaville” together on guitar. The two musicians became fast friends. “When Jimmy came to jam with me, he said, ‘Man, you got a really good gig here.’ I said, ‘Yeah, I do,’” Kapono says. “It’s why I’ve been at Duke’s for 30 years. It can’t be beat.”

The electric energy of performing live is what first hooked Kapono as a kid growing up in Kapahulu. His parents were part of the congregation at Kawaiaha‘o Church. Kapono joined the church’s children’s choir at age 5. “I was a shy kid. But in choirs, nobody can tell who is singing. It’s one voice,” he says. “Later I learned that, once I’m on stage singing or playing music, that shyness all goes away.”

When Kapono was 10 years old, he went to a church retreat at Camp Erdman, where one of his friends was playing guitar. Kapono became mesmerized by the sound of the instrument. “My buddy handed me the guitar and told me to try. I didn’t know how to play so he showed me one chord, I think it was the D chord, and that was it.”

In 1969, Kapono watched the Jimi Hendrix Experience perform live at the Waikiki Shell. Technical problems with the band’s amplifiers ended the show after 30 minutes; Hendrix offered refunds or invited the crowd back the following night for a makeup show. Kapono opted to return the next night and experienced a three-hour concert that blew him away. The 17-year-old couldn’t believe the sounds that Hendrix was making on guitar or the incredible showmanship he witnessed on stage.

Music became an interest for Kapono as a young man. However, sports had been his focus all throughout school. He attended Punahou on a baseball scholarship and was accepted to the University of Hawai‘i to play football. A string of knee injuries ultimately forced Kapono to quit the game, so he decided to shift his focus to playing music as a possible career after college.

Kapono began singing and playing guitar in Waikiki lounges before booking an overseas gig in 1970 as part of the backing band for the Twin Sisters, a duo from Chicago. What began as a six-week tour of Thailand became a two-year ordeal that left Kapono and his fellow bandmates stranded when his band’s booking agent went bankrupt a month into the tour. It was at the height of the Vietnam War. They had no money, no place to stay, and only two tickets to get home, which Kapono and the other musicians gave to the sisters.

“We got stuck in Vietnam and ended up playing for the troops,” remembers Kapono, who could hear the sounds of cannons and gunfire in the not-too-far distance. After a year playing at remote military bases across Vietnam for $20 a month — then another year playing in Thailand — to earn enough for a plane ticket to Hawai‘i, Kapono returned with a newfound sense of purpose. “I matured a lot real fast being in that situation. By the time I got back, music was my passion.”

A friend introduced Kapono to guitarist Cecilio Rodriguez and the duo clicked instantly. Their vocals and guitar sounds meshed as if they had been rehearsing for years. They formed a band, Cecilio & Kapono, and began playing nightly at a club in Waikiki called The Rainbow Villa. “And nobody showed up,” says Kapono. “Then one day, we opened for Frank Zappa.”

At the former Civic Auditorium, Cecilio & Kapono played a 15-minute set before a Frank Zappa concert in 1973. When they were finished, the duo quickly got off stage. The audience was roaring. “Frank came out and said, ‘Where are you guys going?’ I told him that we had a gig in Waikiki,” Kapono says. “He said, ‘They’re still cheering for you, get back out there!’”

By the time Cecilio & Kapono finished their set and got back to Rainbow Villa that night, there was a line around the block. Kapono thought the bar hired another band at first, until he realized the crowd was there for them. “The bar was packed for the next eight months. Everything changed after that.”

Cecilio & Kapono became the first Hawai‘i group to be signed by a major national record label, Columbia Records. The New York Times would call Cecilio and Kapono “Hawai‘i’s answer to Simon and Garfunkel.” Over the next two decades, the duo would release close to a dozen albums, including the inaugural self-titled Cecilio & Kapono in 1974, Elua in 1975, and Night Music in 1977.

Cecilio & Kapono were on tour in the early 1990s when restauranter Rob Thibaut approached Kapono with his vision of a new restaurant and bar right on the beach at Waikiki. Thibaut imagined Kapono singing and playing guitar with Diamond Head in the background.

“We were friends — I played at Rob’s wedding — and he really wanted me to play at this new spot. I told him I would love to. But at that time, our C&K tours went for six months...” says Kapono. He considered what this new residency would mean. Not only the chance to connect with new and old fans but also have a regular venue in Waikiki to call home.

More than three decades later, Duke’s is still a home for Kapono — who has since gone on to release 20 solo albums (including two live albums recorded right at Duke’s Waikiki), a Grammy nomination, and more than 20 Na Hoku Hanohano Awards. In 2018, Kapono and his wife Lezlee Ka‘aihue founded the Henry Kapono Foundation, working with schools to provide music education scholarships and elevating Hawai‘i’s music industry through social services and performance opportunities.

Last year, Kapono’s We Are Friends concert at the Maui Arts & Cultural Center raised more than $200,000 for those impacted by the Maui wildfires. In 2020, the Foundation helped distribute $180,000 worth of Foodland gift cards to 360 local musicians and families that lost income as a result of the pandemic.

“I try to be the best I can every day, whether that’s at Duke’s on Sundays or in my community,” Kapono says. “I’m still passionate about local music and what I do. I’m still going strong.”