"My thesis is his most natural habitat seems to be on the ocean bed half way between the two, hence the number of nautical subjects, including people striding along the bed of the ocean in the fashion of Ulysses," O'Brien says.
Not that Macleod has ever been about fashion. He paints in a sort of loose, painterly expressionist style that ignores fashion.
"You find your own language that suits you, and often it isn't in fashion. I think in New Zealand there is more of a pressure to be in fashion. Australia is just that little bit bigger where you don't have to be so much," he says by phone from his home in Sydney.
You find your own language that suits you, and often it isn't in fashion.
"In fact a lot of that expressionist painting has been in fashion a while, sort of painterly. A number of young artists are working in that thick style and doing quite well.
Ben Quilty winning the Archibald Prize for portraiture may have swayed other young painters to use impasto and painterly gestures, but from the other end of his career Macleod looks on with wry amusement.
"The punters love it, they think it is beautiful and thick, but it never dries — it is sort of like soup inside, it's not archivally good at all.
"I don't think my paintings are that thick, they're actually quite economical. I don't stick it on with a paint knife."
"My feeling is to look for your way of expressing yourself rather than what everyone else is doing. Also whatever vehicle you use, paint, video, photography, should relate to what you are doing, what you are saying.
"That bit is the important bit, the end product on the wall. I would rather people not notice the paint but feel the dirt, feel the earth or fire or water or whatever, rather than the paint."
Macleod grew up in Christchurch, specifically Lyttelton.
At Canterbury University's Ilam Art School in the mid-1970s he was taught by modernists like Bill Sutton and Don Peebles.
Another teacher, the photographer Laurence Aberhart, took his students to places such as Cass or Kaikoura, to demonstrate his philosophy of landscape; where you found the place, you found the subject and sat in front of it and worked towards an understanding of it.
It gave rise to Macleod's practice of painting en plein air whenever he has the opportunity.
Macleod left for Sydney at the start of the '80s, where he added to his immersion in the work of painters such as Colin McCahon, Toss Wollaston, Phil Clairmont and Tony Fomison, engaging with the likes of Sydney Nolan, Fred Williams, Arthur Boyd and Tony Tuckson.
He was drawn to the rawness of Australian painting and was able to make connections, such as comparing McCahon's kauri paintings with those done at the same moment in the '50s by Williams, as both wrestled with the challenges thrown up by Cubism.
"Abstract expressionism was something [my generation] had to get over, but it was nothing like cubism, which all of those people had to somehow deal with."
He explored urban Sydney, then started taking his pencils and brushes into the Blue Mountains and further afield, bringing back the results like some trophy from the landscape.
"It's not about scenery, it's not about the picture, it's not about the landscape tradition. It is about going out there and confronting something in a way that is uncompromising and risky," says the curator O'Brien.
As his family arrived, they started turning up in the paintings — O'Brien rates the paintings of the artist's children as some of his best: "tough, interesting, challenging, not sentimental."
Macleod's Australian career got an early boost in 1982, when novelist Patrick White bought the largest work at his first show at Watters Gallery in Sydney and promptly donated it to the Wollongong public gallery.
Another fan is the New Zealand author Maurice Gee, whose novel Ellie and the Shadow Man includes a (female) painter painting figures in landscapes based on Macleod's work.
The real spotlight came on in 1999 when Macleod won the Archibald, one of the most prestigious and hotly contested art prizes in Australia.
"I did not initially see the painting as a portrait, but it had a head in it so I turned it into a self-portrait. I put it in as a bit of a laugh. It was quite cynical really. I knew they always put in a weird one to keep the controversy happening. "Luckily the judges were looking for painting rather than portraits that year."
In the aftermath he got more attention than he felt comfortable with.
Macleod doesn't follow a set routine, but he's often to be found in his home studio in the afternoon.
"The way I paint is frenetic, an attempt to get emotion or energy into the painting. I tend to bash the shit out of it then go back later and look.
"I find when I am painting it is very hard to make informed judgments on what I should do and shouldn't do. I can make some judgments, not subtle ones.
In recent years, Macleod has spent more time in New Zealand, often borrowing a friend's studio in Queenstown.
"I like working between Australian and New Zealand. New Zealand represents the old, history, heritage, memories, while Australia represents new places. It is such a harsh place, especially the interior.
"I spent a lot of time in the mountains growing up, climbing and tramping, but I didn't see landscape as subject matter until I came over here. The landscape crept in round the sides."
●Euan Macleod: Painter runs from March 20 - May 20 as part of the Auckland Arts Festival at the Wallace Art Centre