Gerhard Richter's Dusenjager (1963) has sold for $27.1m at Phillips.
The work is a particularly fine example of Richter's photorealistic paintings, which he began producing in the early 1960s after being exposed to pop art.
It's one of a series of eight canvases he painted that depict warplanes. Like many of his works from this period, the series articulates the tension and uncertainty of a divided, post-war Germany.
Dusenjager last sold for $11.2m in 2007 and has achieved growth of 10.3% per annum since then.
Richter is among the world's most valuable living artists.
His Abstraktes Bild paintings are now the most sought after, in contrast with a few years ago when his photorealistic works were setting record sums.
Roy Lichtenstein's Nudes in the Mirror (1994) was another highlight, realising $21.5m.
Lichtenstein's Nudes series was the last he worked on before his death in 1997.
He explained: "My nudes are part light and shade, and so are the backgrounds, with dots to indicate the shade…
"I don't really know why I chose nudes. I'd never done them before, so that was maybe something, but I also felt chiaroscuro would look good on a body."
His record is $95.4m, set for Nurse (1964) last year.
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