Once called ‘the most important American painter of his generation’, Christopher Wool’s iconic word art and abstract expressionist paintings have been exhibited in museums around the world, and can achieve tens of millions at auction. Here we list his top results in recent years.

Untitled (Riot), $29,930,000 (£23.1 million)

Untitled (Riot) by Christopher Wool

©Sotheby’s

The most expensive painting by Wool at auction, Untitled (Riot) sold for $29.9 million at Sotheby’s in New York on 12 May 2015, over double its $12 million low estimate. Wool was first inspired to make his word painting in 1987. He was walking in New York’s Lower East Side when he saw a white truck with ‘SEX’ and ‘LUV’ graffitied on its side. The contrast between the words and the white background was a lightbulb moment for the artist, who created his own painted version after returning to his studio. These word paintings are now Wool’s most famous and recognisable artworks.

Apocalypse Now, $26,485,000 (£17.2 million)

Apocalypse Now by Christopher Wool

©Christie’s

Created in 1988, Apocalypse Now was one of Wool’s earliest word paintings and the first that he publicly exhibited. The text was inspired by a scene from Francis Ford Coppola’s movie Apocalypse Now, as well as the famous Black Monday Wall Street crash a year earlier. “It was an experiment,” Wool said of making and exhibiting Apocalypse Now. “Previously, I had been making abstract paintings, so it was certainly a departure. I was still young and extremely insecure.” His worries stopped when the gallerist Paula Cooper saw the painting and said it reflected her sentiments exactly. “I immediately relaxed,” recalled Wool.

Apocalypse Now sold at Christie’s in New York on 12 November 2013 for $26.5 million, soaring past its estimate of $15-20 million.

If You, $23,685,000 (£14 million)

If You by Christopher Wool

©Christie’s

The sale of Wool’s If You at Christie’s in New York on 13 May 2014 followed a very successful year for the artist. In 2013, Wool’s major retrospective exhibition opened at the Guggenheim Museum in New York, establishing him as one of America’s most notable living artists. The sale of Apocalypse Now at Christie’s in November 2013 (no. 2 on this list) also set a new auction record price for Wool. If You, a similarly bold and gritty work, sold for $23.7 million against a low estimate of $20 million. Another version of the same phrase sold for a top auction price in 2016 (see no. 10 in this list).

Untitled, $17,159,500 (£10.2 million)

Untitled by Christopher Wool

©Christie’s

Sold for $17 million at Christie’s in New York on 17 May 2017, Untitled came from the collection of prominent New York collectors Emily and Jerry Spiegel. The couple were early champions of Wool and purchased Untitled in 1988, the year it was completed. A total of 25 works from their collection were offered at Christie’s that night in May 2017 – in addition to Wool, there were works by artists like Andy Warhol and Jeff Koons – selling for a total of $116,067,500.

Untitled, $16,965,000 (£11.2 million)

Untitled by Christopher Wool

©Christie’s

“I did a painting with the phrase, ‘CATS IN BAG, BAGS IN RIVER’…it’s a line from the movie Sweet Smell of Success. Sidney Falco, the Tony Curtis character, does a dirty job for J.J. Hunsecker, the Burt Lancaster character, and to tell him that he’s done the job—they’re in the 21 Club so they have to talk in code. It was an important line…I loved the poetry.” Wool said of the meaning behind this painting. Untitled went on to sell for almost $17 million at Christie’s in New York on 10 November 2015.

Untitled, $15,218,750 (£11.9 million)

Untitled by Christopher Wool

©Christie’s

One of Wool’s favourite phrases, ‘RUN DOG’ has appeared in different versions throughout his career. A five-panel variation is in the collection of the Whitney Museum in New York, while a huge, nine-panel variation is in The Broad, Los Angeles. This single-panel Untitled was snapped up in just half a minute of rapid bidding at Christie’s in New York on 15 November 2018.

Untitled, £10,424,900

Untitled by Christopher Wool

©Sotheby’s

Wool has described his painting technique has “a basic process of drawing and erasing. I can spray different qualities of lines and I can erase it with a rag and turpentine… very much if you had a piece of paper, a pencil and an eraser.” The artist is as much known for his monochromatic, expressionist paintings as his black-and-white text art. Untitled, made in 2007, was offered at Sotheby’s in London on 7 March 2018, where it sold for £10.4 million, almost double its estimate of £4.2-6.2 million.

Untitled, $14,165,000 (£8.9 million)

Untitled by Christopher Wool

©Sotheby’s

Created in 1990, Untitled has appeared three times at auction. It debuted at Christie’s in London on 14 February 2012 where it achieved £4.9 million, much higher than its £2.5-3.5 million estimate. It was offered again at Christie’s in New York on 12 November 2014, realising $14.1 million or £8.9 million, almost doubling its value in two years.

Five years later, the painting sold for $14 million at Sotheby’s in New York on 16 May 2019. Although it was a decrease in value in dollars, its price in sterling was £10.9 million – an increase of £2 million since its last sale – which just goes to show that the location of a sale is just as important as its timing.

Untitled, $13,914,000 (£9.6 million)

Untitled by Christopher Wool

©Sotheby’s

“These are words that I would and I could describe Christopher with. I would if I could but he’s already done it himself,” artist Richard Prince once said about Wool. Untitled comes from Wool’s Black Book series of 1989 – a set of 17 word artworks, featuring words like ‘HYPOCRITE’, ‘PRANKSTER’ and ‘CELEBRITY’ in addition to ‘CHAMELEON’. Black Book is considered Wool’s self-portrait and both the Black Books limited-edition lithographs and paintings are among his most sought-after works. When Untitled came up for auction at Sotheby’s in New York on 11 May 2016, it realised $13.9 million.

And If You, $13,605,000 (£9.4 million)

And If You by Christopher Wool

©Christie’s

Painted in 1992, the same year as If You (no. 3 on this list), And If You depicts one of Wool’s favourite phrases, which he has used numerous times in his artwork. “I started in the left hand corner and I went like you would with a typewriter,” Wool said of his process and why the words break so abruptly. And If You sold for $13.6 million at Christie’s in New York on 10 May 2016, achieving much higher than its low estimate of $12 million.

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