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Few names in art resonate so strongly as Andy Warhol. The doyen of pop art and the 1960s New York art scene, Warhol is a figure who has transcended normal reality, becoming not only one of the most revered artists of all time, but also someone whose creations and ideas have steered wider popular culture.

Think of Warhol and images of Campbell’s soup cans - as well as Warhol’s own enigmatic face, his hair wildly askew - will likely flick through your mind. The artist’s multi-coloured images of other famous icons will also be lodged in your memory, with a yellow-haired Marilyn Monroe probably the most prominent among them.

The universal power and resonance of the image partly explains why a silkscreen portrait of Monroe, hand-painted by Warhol - Shot Sage Blue Marilyn (1964) - could soon become the most expensive 20th century artwork ever sold at auction. Due to go under the hammer at Christie’s New York on 9 May, the painting has been valued at around $200 million - the highest pre-auction estimate ever given to a piece of art.

Warhol began his series of Marilyn artworks in 1962 not long after Monroe had died, working from a photograph of the actress originally used to promote the 1953 film Niagara. In keeping with his practice of making multiple versions of the same image, the series extended in 1964 to include five silkscreen Marilyns, with Shot Sage Blue Marilyn among them.

And why the ‘Shot’ in the title? Quite simply, the answer is that the piece literally was shot. Adding to the legendary status of the series, not to mention the aura of Warhol, four of the 1964 Marilyns were reputedly fired at by the artist Dorothy Podber while they were stacked up in Warhol’s Factory studio. The incident was said to have been a case of art world brinkmanship and word play, with Podber responding to Warhol’s offer to let her ‘shoot’ or rather, as he expected, photograph inside the Factory.

Should Shot Sage Blue Marilyn realise its valuation by Christie’s, the sale will surpass Picasso’s Les femmes d'Alger (Version ‘O') (1955), which set a record high at auction for a modern or contemporary artwork of $179.4 million in May 2015. Some experts have even suggested that Warhol’s Marilyn may go as far as to eclipse the $450.3 million paid at auction for Leonardo da Vinci’s Salvator Mundi in 2017.

Either way, the $200 million estimate confirms Warhol’s place at the very pinnacle of the contemporary art market, continuing a trajectory that has seen the value of his work consistently outperform leading financial markets, including the S&P 500, Nikkei 225 and FTSE 100.

Already a star attraction in his own lifetime, the price of Warhol’s art rose dramatically following his death in 1987, with a particularly pronounced upturn from the early 2000s through to the present day. The increase in the value of his work, year on year, has seen Warhol outperform stock markets and the wider art market for most of the last four decades, including sales of work by other notable 20th century artists, such as Picasso and David Hockney.

As an indication of the scale of appreciation, among previous sales of the 1964 Marilyns, Shot Red Marilyn sold at Christie’s New York for $4.07 million in 1989, while a decade later, Orange Marilyn sold at Sotheby’s in New York for $17.3 million. Considerably outperforming its original estimate of £4-6 million, the latter made a significant splash and has been credited with sparking the escalation that ultimately led to the value of Warhol’s work today.

May 2022 could now become another important moment in the artist’s ongoing story. While Christie’s looks to set a new benchmark with Shot Sage Blue Marilyn, other upcoming Warhol sales include a large-scale, acrylic and silkscreen ink on canvas self-portrait being sold by Sotheby’s as part of its Macklowe Collection auction on 16 May. Over two meters square in size, the camouflage-style portrait was made in 1986, not long before Warhol died, and has been given an estimate of $15-20 million.

Just as Warhol helped to immortalise figures like Monroe through his art, his self-portraits were an integral part of his practice. Warhol the celebrity and Warhol the artist are fused in the portraits, heightening his allure, yet retaining his mercurial, enigmatic distance.

With Warhol having made his self-portraits over a 20 year period, Mintus is currently offering the opportunity to invest in an early example from 1966. Showing the artist in a contemplative pose, his eye scrutinising the viewer, the work is offered at an overall price of £3.8 million, with qualified investors able to make investments starting from £2,500. The last painting from the series to appear at auction realised $6.5 million in 2016, having been given a lower estimate of $4 million.

One thing that is clear from the history of the trade in Warhol pieces is that investing in his work can mean joining an illustrious group of collectors. To own a Warhol, though, is also to own a piece of collective memory, a storied artefact bound up with the visual culture that surrounds us.