During the years, their paths have crissed and crossed but until now flamboyant entertainer Mika and radio personality Mike King have never worked together.
As King says his one-time brand of racist, sexist and homophobic humour didn't exactly gel with Mika's message of love and acceptance.
But times change and now their shared concern about youth suicide will see them together for the first time on stage.
They'll join singer Megan Alatini and celebrity guests at the Aroha Festival of Ideas All-Stars Gala Fundraiser this month to raise money for their respective charities.
The festival is run through the Mika Haka Foundation, founded by Mika to turn young lives around through the performing arts and physical culture.
King's own experiences of mental illness and drug abuse have seen him retire from the comedy circuit to run The Key to Life Charitable Trust and the weekly Nutters Club radio show on Newstalk ZB.
The trust works in schools and the community encouraging young people to be open about their thoughts, feelings and experiences.
Mika approached King about joining forces and the dynamic duo see it as the start of what could become a rewarding partnership.
"How did I get involved?" King chuckles, "Because this whirlwind called Mika came to see me and said, 'we're going to do this, we're going to do that and this is how we're going to do it!'"
He says his wife, Joanna, told him she knew Mika was "legit" because within a couple of days, he'd sent King mock-ups of artwork and a draft festival programme.
Despite their differing backgrounds, King and Mika share firm ideas about the importance of raising youngsters to feel loved, supported and accepted for who they are.
King says he talks to school pupils about the "inner critic" - that "little voice" we all hear constantly putting us down and telling us what we can't do.
"For many kids, that's the first time they've had an adult talk to them openly about this stuff and I can see them nodding and realising exactly what I'm talking about."
Mika speaks of "emotional vampires" - described as people in your life who make you feel "blah!"
"I say, 'get out your phones, block them, unfriend them, delete them - do what you have to do so they're not in your life anymore making you feel bad'."
Both have also had life-changing moments when they weren't happy with the direction they were heading in.
King says his comedy was always a way to earn acceptance and make friends, even when he didn't want to tell the jokes he was making, and he's far happier being honest about himself.
Mika acknowledges turning points when he felt like a token gay performer conforming to stereotypes about how he should be.
"I've always been a 'gender bender' and I look at these kids and say, 'Am I gay? Transgender? Intersex? Honey, I was all those things before you were even born'. I don't need to be put in a category - nobody does."
Older and wiser, they say they've been in the business long enough now to want to run their own affairs, to be discerning about who they accept funding from and to know actions speak louder than words.
• The Aroha Festival of Ideas includes a film festival, dance works including a piece by emerging young choreographer/dancer Eddie Elliott, pop-up costume exhibits, a dance party and the All-Stars Gala Fundraiser at Halo Nightclub on Saturday, February 18. For more, go to mhf.co.nz
Where to get help:
• Lifeline: 0800 543 354 (available 24/7)
• Suicide Crisis Helpline: 0508 828 865 (0508 TAUTOKO) (available 24/7)
• Youthline: 0800 376 633
• Kidsline: 0800 543 754 (available 24/7)
• Whatsup: 0800 942 8787 (1pm to 11pm)
• Depression helpline: 0800 111 757 (available 24/7)
• Rainbow Youth: (09) 376 4155
• Samaritans 0800 726 666
• If it is an emergency and you feel like you or someone else is at risk, call 111.