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The Funniest People in Hawai‘i

It takes one to know one, so we asked award-winning comedy writer Charles Memminger to choose the most hilarious comedians the Islands have produced.


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Frank De Lima

Frank De Lima

Trying to identify the “funniest people in Hawai‘i” is something like trying to identify the shortest munchkins in Munchkinland. There are so many of them. Hawai‘i is a sort of funny people breeding ground, a tropical petri dish that provides a rich, nurturing environment for humor to grow and thrive. Humor is an organic consequence of throwing a ridiculous number of diverse cultures and ethnicities onto a clutch of islands in the middle of an empty, balmy ocean. And balmy is a key factor. Because if you throw a bunch of people together on cold, forsaken islands in the middle of a freezing ocean, you don’t get humor, you get Vikings.


Now, let’s be clear: There is no way I can single out all the funny people in Hawai‘i. Because most of them work in offices, or at the Department of Public Works or in restaurant kitchens. We remember them from school, that funny guy or girl who made us spew milk through our noses with an unexpected antic or observation. They never ended up on stage or TV or radio. But they are still around, still funny.


So I have to concentrate on the standouts, the funny people who made names for themselves in the Islands. Where do you start, historically? I’m sure there were some funny folks around back in King Kamehameha’s day. A court jester, if you will, who amused the royal family with bits like, “Hey, I just swam in from Maui and, boy, are my arms tired!” There was probably even some sailor in Lahaina telling whale jokes during Herman Melville’s time. (“Three whales walk into a bar …”)


I’m no cultural anthropologist, but from talking to a number of local comics and entertainers, it seems that modern Island humor, heavily influenced by cultural and ethnic differences, can be traced back to the original “Portagee jokes,” jokes made at the expense of the Islands’ Portuguese residents during the early sugar plantation days.


Comedian and proud “Portagee” Frank De Lima explained it to me this way: “The Portuguese were the foremen on the plantations and they were very strict. Some of them were mean, actually. When you have someone who is mean, you are going to make jokes about them.”


De Lima has kept that tradition alive in his more than 40 years of comedy by not only telling Portagee jokes but skewering all ethnicities equally and, if not in drag, then in outrageous costumes. De Lima is one of Hawai‘i’s funniest people, but that hasn’t kept him from being lambasted in this New Age of Hypersensitivity for continuing to indulge in ethnic humor. Lee Cataluna, a columnist with The Honolulu Advertiser, a noted playwright and a former standup comic herself, chastised De Lima in a column a few years ago for continuing to make Portagee jokes. De Lima laughed it off, saying that ethnic jokes in the hands of professionals before a paying crowd who know what they are going to hear is fine while ethnic jokes told by some idiot in an office specifically to demean or insult someone … not so good.

Detective by day, Decca recording artist by night, Sterling Mossman was known as the "Hula Cop."

Photo: Archives of Honolulu Magazine


I use the example of telling “Portagee jokes” in order to draw an arbitrary historical starting point for identifying some of Hawai‘i’s funniest people in modern times (i.e., the times when mixed drinks with umbrellas in them first became popular) because humor at the expense of plantation foremen became a mainstay of comedy in Waikiki. And the godfather of ethnic and pidgin humor came from an unlikely place: the Honolulu Police Department. He was a detective named Sterling Mossman. Throughout the 1950s and 1960s, Mossman held court at the Barefoot Bar at Queens Surf. He was known as the “Hula Cop,” because he would sing, dance and tell outrageous stories until the early morning hours and then go to his job as an HPD detective. He was part Portuguese, so Portagee jokes were an inevitable part of his repertoire.


Legendary promoter Tom Moffatt knew Mossman well. “We put him in a show once at the Civic Auditorium; he was funny as hell. He told a joke about the missionaries, how they came to Hawai‘i and wanted to teach the Hawaiians Christianity. They asked the Hawaiians to bow their heads and when the Hawaiians raised their heads, their land was gone.”


The Barefoot Bar was ground zero for this new brand of local comedy. Mossman was the ringleader, along with the likes of Lucky Luck, a zany radio personality, and Kent Bowman, known as K.K. Kaumanua [say his name out loud]. They told stories, sang songs and, when a celebrity from the Mainland happened to come by (and they did a lot), they became part of the show. Imagine the scene … songwriter Kui Lee singing “I’ll Remember You” downstairs at Queens Surf while Bobby Darin joined Mossman on stage up in the Barefoot Bar. Mossman even allowed an unknown Hawaiian-Chinese crooner from a little bar in Kāneohe to sit in for him occasionally. His name was Don Ho, and his relationship with Mossman became pivotal in an unlikely comedy genealogy that extends to this day.


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