It seems like a new Jean-Michel Basquiat fashion collaboration drops online most weeks, from a £20 Uniqlo crew neck T-shirt to a kimono or a sports bra. But more than 35 years since his death in 1988, would the New York artist have been flattered or horrified by the mass marketing of his art?

Basquiat’s premature death at 27 means that questions will remain as to whether he would have signed off on things like bathmats on Redbubble or Ligne Bath’s Trumpet candle. How would he, for example, have felt about a Basquiat collaboration with MeUndies underpants – with the tagline: “Jean-Michel Basquiat … taught us all to look inward and find our authentic self. MeUndies always strives for authenticity.”

A new book, Jean-Michel Basquiat: The Making of an Icon, by Doug Woodham, the former president of Christie’s auction house in the US, hopes to answer this question and unpack the neo-expressionist’s journey to becoming one of the most famous artists in the world. “I think comparing [him] to Keith Haring is a good way to try and understand it,” he said.

Haring was a contemporary and friend of Basquiat’s and, according to Woodham, “was the first contemporary artist to realise he could put his motifs on a keychain and sell it at pop-up shops, knowing that it wouldn’t hurt his market value”. While Woodham believes Basquiat would be “excited and happy” about how the estate has marketed his artworks, he is unsure the artist would like all the merchandise upon which his work appears.

Friend and artistic collaborator Al Diaz, who co-created Basquiat’s Samo graffiti tag, is more definitive. He believes the merch dilutes the meaning and message of the art in the process. “It’s abusive at this point. It’s demeaning to the artist, offensive and disrespectful,” he says over the phone from New York. Was there anything Basquiat would have categorically hated, I ask? “There was that Barbie doll they did and a door mat. It seems so over the top and thoughtless,” he says. “It’s like, ‘OK, let’s print this on everything and anything’.”

And yet the spectre in the popular consciousness of Basquiat as the starving junkie punk artist is complicated by Woodham’s portrayal in The Making of an Icon. Once the artist started making money, he is characterised as “loving cash”, his ambition leading him to make a beeline to a friendship with Andy Warhol and even self-branding in a costume of designer suits flecked with paint. He had seen his fellow artist Julian Schnabel garnering attention for showing up to parties wearing pyjamas. “He chased fame very strategically and deliberately,” says Diaz. “He was very, very clever and had a special charm.”

The book posits that three key traumas shaped the artist: a near-fatal car crash during childhood; the sometimes violent breakdown of his parents’ marriage, which led to his mother, Matilda, having a nervous breakdown; and finally his mother’s wish for his father, Gerard, to raise him and his two sisters alone.

Gerard Basquiat was born in Haiti, but fled the country because of civil unrest, first going to Miami before ending up alone in New York. The artist’s father only spoke French, but after learning English, he became an accountant. “He’s really impressive,” says Woodham, “he’s also very domineering”.

Gerard Basquiat often butted heads with his son. “Everybody wants to be recognised and supported by their parents,” says Diaz. “He had a lot of anger and disdain and disappointment because he never received that from his dad … having a bisexual, art-orientated son was not in [his father’s] playbook.”

After Basquiat’s death, his estate was taken over by his father, and their layered relationship bled into our modern understanding of the artist. In The Making of an Icon, Gerard is portrayed as savvy – he partnered with Keith Haring’s legal team who taught him about licensing – but also, understandably, controlling of his son’s narrative.

Woodham spoke off the record to gallery curators who said that Gerard Basquiat would lean on them to omit certain parts of the biography (his mother’s role in his life, the effects of his childhood trauma and the depths of his drug habit and bisexuality), so a more “heteronormative” narrative would be promoted. A narrative, one would assume, that would make him more palatable to both the elite art market and the wider public.

There was a uniformity to how all the museum and gallery catalogues were written, says Woodham. And yet, he says: “I think all these strands add a richness to the guy’s character. I think it makes him more compelling and interesting.”

The reach of Basquiat’s art is undeniable. And for a younger generation, many of whom only know him through this merch, it simply doesn’t matter that his art is omnipresent.

“It’s fascinating to talk to 30-something collectors,” says Woodham. “For them, Basquiat has always been in the pantheon. And the first time they ever heard of him was from a Uniqlo T-shirt.”