Kaipo and Madonna
Ooowee, he a good looking son of a bitch! Madonna ain't immune! Invited him straight to Japan after the shoot! | Photo: Herb Ritts/Rolling Stone

Gallery: When Madonna Loved Kaipo!

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.

Rs85madonna3

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.

Rs85madonna2 Rs85madonna1

 

Comments move to a new system on Tuesday 22 September 2026. Your existing comments come with you. From that day you comment with wpDiscuz instead of Disqus, right here on the same page.
Load Comments