Two works from Andy Warhol's Death and Disaster series have sold for a combined $100m (£59m).
Race Riot, 1964 - inspired by pictures of a notorious civil rights protest in Birmingham, Alabama - went for $62.9m (£37.3m) at Christie's in New York.
The 1962 painting White Marilyn, completed shortly after Marilyn Monroe took her life, sold for $41m (£24m).
Alongside works by Mark Rothko and Barnett Newman, the paintings helped Christie's set a new auction record.
In total, the sale of post-war and contemporary art raised $744m (£441m), the highest ever total for a single auction.
"Well we've actually made history tonight," said Brett Gorvy, Christie's head of post-war art. "It was a momentous evening."
The previous highest figure was set in November 2013, also at Christie's, when the grand total was $691.5m (£430.8m).
Ten auction records were set at Tuesday night's sale, with works by American sculptor Alexander Calder and artist Joseph Cornell fetching new high prices.
After a fierce round of bidding, Newman's Black Fire I, a 1961 canvas showing a thick column of black alongside smaller ribbons of white and black, made $84.2m (£50m), almost double his previous highest price.
Francis Bacon's Three Studies for a Portrait of John Edwards surged to $80.8m (£49m), from an opening bid of $50m (£29.6m).
Created in 1984, it shows the painter's companion, and sole beneficiary of his will, in a relaxed pose sitting on a stool with his right leg crossed over his left knee.
It came onto the market a year after Bacon's 1969 Three Studies of Lucian Freud sold for $142.4m (£85.5m) - the most expensive artwork ever sold at auction.
Rothko's Untitled, a large abstract oil painting with colours ranging from a silvery mist to a deep violet, fetched $66.2m (£39m).
It was sold on the same day the artist's Black on Maroon went back on display at Tate Modern, 18 months after being vandalised by graffiti.
And Jean-Michel Basquiat's seminal 1981 painting of a regal warrior figure, which elevated the artist from the underground to the mainstream, sold for $34.9m.
All but four of the 72 lots on offer at Christie's were sold, with bids coming from 35 countries around the world.
"These are incredible statistics," Gorvy said.
"Everyone asked me last year 'are we in a bubble?'. We're in the middle of a fantastic moment, a fantastic moment which is rising with great foundation stones, fantastic collectors and a very international spread."
Despite the global economic downturn, the global art market has remained relatively robust in recent years.
The European Fine Art Foundation annual report showed the market rose 8% to $65.9bn (£39bn) last year, its highest level since 2007.
High prices are expected again on Wednesday night, as Sotheby's hosts its own sale of modern art.
A group of six Warhol self-portraits is expected to bring $25m, while Jeff Koons' 7ft-tall (2.1m) sculpture of Popeye has a similarly high estimate.