Step back into 1985 with the WSL's newest stud!
Did the sexy-as-a-wolf Kaipo Guerrero bolt you to your computer during the Tahiti Pro too? The former pro surfer (Hawaiian champ, NSSA open champ, three years top 16 Bud Pro Tour) has a rough-hewn danger that takes the imaginative viewer down a rabbit-hole of scenarios. Kaipo ain’t no twink!
Can you count the ways? Don’t it make you want to POV a PAWG gittin’ IR on that BHC? No? Yes?
But being in the spotlight ain’t new for this waterman who learned to surf at Waikiki and who has made four crossings of the Molokai channel in his little canoe.
Kaipo, who is 48 years old, has always carried the gun of ultra-handsome. Back in 1985, when he was eighteen years old, he was the star of a Herb Ritts shoot with the most popular singer in the world, Madonna. The gal loved that sugar so much she stole him away to Japan.
Thirty-one years later, Kaipo has returned to call the most prestigious events in surfing, including the now-legendary Tahiti Pro.
But that time, that era, when the world revolved around Madonna and Madonna revolved around a teenager from Oahu, oh man, it’s beautiful.
Relive here the Herb Ritts shoot.
Spread one: Madonna jams uke with Kaipo on her left, in pyjamas. In green suit, Kaipo grasps the New York crooner.

Where’s Kaipo? Black shirt, grey jacket. Kelia Moniz’ daddy Tony is there having his foot grabbed by Madonna but y’know it’s the stud in the back who eating good.

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I’d love to rag on Kaipo about basically being a paid lap-dog, but thats just because I’m jealous. When I was 18 I was still playing with space lego.
He looks a bit AIDsy these days.
I believe I see a Jamie Brisick in the lower left photo.
And, yes, you are! Both, on ground, in the penultimate spread and to Madonna’s right in the final photo…
wasn’t snoop and 2pac hitting it round that time?
I think the more appropriate question is…who wasn’t hitting it at that time.
He looks how I would look if I was gay and tanned.
Or even good looking ;).
Any story, article, quote, inference, blurb or meme on BG that mentions a 40+ year old stud should only be in direct reference to me. And me only.
Now…I will return to my bottle of percocets and general incapacitation from abdominal surgery and let the apologies flow in (I’m lookin’ at you Derek).
On a side note…if you’re looking for a little Madonna nostalgia Amazon has the old ’80’s movie “Vision Quest.” It’s her feature film “debut” and has a great performance from Matthew Modine along with a young (and ’80’s hot) Linda Fiorentino.
oooh like Last Seduction hot? That was peak Fiorentino.
I don’t remember that movie but she is bra-less in quite a few scenes so that’s always a plus.
Madonna is not, was never, nor could be ever, a PAWG.
Nor would I ever dare to claim such a thing. The POV a PAWG thing was fantasy.
I understand that now… I reread five times after I posted and realized that. That’s what I get when I post at 2:30 am on a Sunday. Soz, Derek. Confession of this episode just reinforces to me the fact that I have a problem…
P.S. now I’m wide awake in daydreams of Julie Cash!
Does that make it conception inception?
You like pianists?
Yes, that one.