Although it hasn't all worked - their 2012 EP with dubstep producer Rusko was a particular misfire - there's no denying the impact their first three albums had on early 90s hip-hop.
It's from those albums they'll be cherry-picking songs for Saturday's late afternoon performance, and Sen Dog knows there's one song that they have to play - their 1993 single Insane in the Brain.
The song's ridiculous-yet-addictive hook showcased Sen Dog's fellow rapper B-Real's Nasal delivery, Eric Bob's percussion style and DJ Muggs' booming old-school beats - a combination now known as the signature Cypress Hill sound.
But Sen Dog says it was never supposed to be a single.
"It was more like a song we put out to put out to let people know Cypress was coming back for a second record," he says. "We thought, I Ain't Goin' Out Like That would be the bigger song. Everywhere we go people go crazy for Insane."
The other thing Cypress Hill are known for is their pro-marijuana stance. Many of their albums feature marijuana leaves on the cover, much of their lyrical direction is based around weed, and Black Sunday includes songs called I Wanna Get High, Legalize It and Hits from the Bong.
Sen Dog says they try to keep things clean on the road, so problems with authorities these days are rare. "The whole clan is pretty strong-minded about not travelling to other countries with anything crazy.
"It's a form of high disrespect to come into somebody's country carrying stuff. They're letting us come in there and do work and we're going to come in there straight. We don't want any trouble, especially with governments and airports."
Besides, wherever Cypress Hill go, the best weed seems to follow them.
"If I really want it, once I get to the venue where I'm going I'm pretty sure someone's going to have some pretty good weed," Sen Dog says.
When TimeOut says he should be well catered for at a reggae festival in New Zealand, Sen Dog laughs: "I recall that about New Zealand."
Who: Cypress Hill
Where and when: Raggamuffin, Trusts Arena, Auckland
With: UB40, Ice Cube, Chronixx and more
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