Since his beginnings in the punk/new wave movement of the mid-70s, he has released over 30 studio albums, making his way through many genres from blues to country, jazz and classical string quartets.
He has appeared in operas and has written ballets and taken small roles in various movies from the Spice Girls' Spice World, to Hurricane Katrina TV drama Treme. He had his own television show in which he interviewed fellow musicians; he co-operated with scores of artists, worked as a producer, holds an honorary doctor title and -- always a sure sign you have made it into pop culture -- appeared as himself on The Simpsons.
But now, the notoriously prolific musician - born Declan Patrick MacManus in 1954 - says, he's done with making records, but still far from announcing his retirement.
"I have to make a living. That may sound like a joke, but it isn't. I have a lot of responsibilities and I've always invested the money I earned back in other projects and the making of the music," he tells NZPA.
"I can't pretend I haven't done well from it but I certainly by no means am in any position to retire.
"But I think, as you go on in time, you look at what is really enjoyable and satisfying.
"I am doing the thing that I want to do the most now, but I reached the point where I don't have to think about anything other than that, because there are a lot of valuable things in life, and life is short," the father of four-year-old twin boys says. "So you really want to make sure, that you don't spend your whole time with work and miss other things that are crucial in your life.
"I don't make records anymore, so that's going to clear a lot of space out," he reveals.
He released his last record National Ransom in November featuring all members of his bands The Imposters and The Sugarcanes and a range of other collaborators like Vince Gill, Marc Ribot, Buddy Miller, and Leon Russell and is planning now to concentrate solely on performing.
Although he ventured down many musical and artistic paths, he says he never had a big plan behind things.
"Some of these things have been an adventure, but some things have been suggested and it would have seemed foolhardily not to give it a go," he says.
"I never had a master plan whatsoever, which is very odd when you think of everything I ended up doing.
"But ambitious is where you say yourself, by the time I get to a certain age, or by this time next year I got to be here otherwise I would have failed."
But he says he hasn't had this feeling since he was 25 years old.
"I think at that point I had some thoughts what I should be achieving before that and then I realised that has all been ridiculous and ever since I have just sort of been wasting other people's money, doing what I want to do," he says.
Being hailed not only for his musical talent, but also for being a virtuoso at playing with language and not shying away from picking on current events in his lyrics, he still doesn't see his work as a commentary on society.
"No, I just write what I am interested in, in that moment, and some of the songs come out tender and some come out critical and it's not like a little badge I wear. It's not that I am in the Girl Guides and I learned how to tie knots or I learned how to light fires, it is just different songs come out different way.
"I don't know what use they are, I don't know if they are of any use at all. I just don't want to sing the same songs, the whole of my life, so you have to write some different ones and then you find how useful they are to you for a little while and some of them stick around and some of them don't," the 56-year-old says.
Now that he has decided to put working an albums on the back burner (it's just unfathomable that he's actually "done with it" forever), he might find more time to write. Although it's not exactly a book every day, he says, he's been working on a book project for a number of years.
"I don't know what it's going to end up being, but you know when it comes out, and I know as well, at the moment I don't.
"I have been working on it, but I don't know what to call it. If you say biography to people, they are going to think it's going to be like the secret to everything and how you did everything, sort of re-fighting every battle that you ever had or re-living everything, all that stuff that people like to put in when they have no more ideas. But I would like to come up with something that is a little bit different, but, we'll see."
Costello says he was looking forward to playing his first gig in New Zealand since the ill-fated 1999 Sweetwaters Festival, which left him and many other artists without pay and landed organiser Daniel Keighley in jail. He was to play the inaugural GrassRoots Festival in south Auckland scheduled for two days over the Easter weekend together with artists like BB King and Grace Jones.
But the promoters cancelled the event last week, citing bad tickets sales after the devastating Christchurch's earthquake. Now Kiwis have to pace themselves a little while longer.
Costello says he certainly isn't holding a grudge against New Zealand -- he'd love to come, he just needs to be invited.
