La Gommeuse achieved the top price of $67.5m (£45m) at Sotheby's, as part of their Impressionist & Modern Art sale on Thursday.
And Van Gogh's atmospheric landscape, Paysage sous un ciel mouvemente, sold for $54m (£36m), helping to take the evening's total to $306.7m (£203m).
Simon Shaw, co-head of Impressionist and modern art worldwide, called it "a small sale that packed a real punch".
He added: "Each season Picasso has the remarkable ability to surprise, and tonight was no exception, with the unusual appearance of two Blue Period works, which set new benchmarks - both in oil and on paper."
La Gommeuse, described as most the important blue period Picasso to come to the market in a generation, was painted in 1901.
The portrait is of a nude unnamed woman. Gommeuse, which translates into English as 'gummy' was a sexually charged slang word of the time for cafe-concert singers and their songs.
It features a second portrait on the reverse of the canvas, which was hidden for a century until its discovery in 2000 during conservation work.
The caricature of Picasso's friend Pere Manach was apparently intended as a gift for the Catalan anarchist who shared the artist's studio flat in the Boulevard de Clichy in Paris.
The painting was one of 47 works on offer, with just over three-quarters finding buyers.
At least two of the top 10 lots were bought by Asian private collectors, continuing a trend of recent seasons.
The $306.7m (£202m) total comfortably beat the $275m (£182m) low pre-sale estimate. Sotheby's had tagged the high estimate at about $370m (£244.5m).
This total brings Sotheby's sales of Impressionist & Modern Art in just the past 24 hours to $575.8m (£381m),
Earlier this year, Picasso's Women of Algiers became the most expensive painting to sell at auction, going for $160m (£102.6m) at Christie's in New York.

Harris-Wright, 28, who had a season at Bristol in 2011-12, won a European Champions Cup medal at Leinster.
The club have also added Harlequins tight-head prop Tyler Gendall, 22, Jersey Reds back rower Nick Haining, 26, and Watsonians scrum-half Reiss Cullen, 20.
"We're pleased to bolster our options with these talented young players," interim head coach Mark Tainton said.

Witnesses told officers they heard a gun being fired near Anfield Road Primary School at about 09:00 GMT.
Pupils and staff there and at the nearby All Saints Catholic Primary School have been ordered to stay indoors while police investigate.
Ch Supt Mark Harrison said it "beggars belief" it would happen at a school.
Members of the public told police the shot was fired at a dark coloured car by a white man in a grey hooded top who was on foot.
A Merseyside Police spokeswoman said local hospitals had been checked and "no-one has sought medical attention for injuries caused by a firearm".
She said officers were making house-to-house inquiries and studying CCTV footage of the area.
Ch Supt Harrison said the attack "appears to be targeted" and was particularly worrying as "a child could have been seriously injured or worse".
He said police wanted to hear from those inside the car "so we know they are safe".
Anfield Road Primary School's headteacher Clair Drew-Williams said her pupils were "safe and unaware of the incident".
"The site was not evacuated, the school day is continuing as normal and a trip for some pupils took place as planned," she said.
A new record for a blue period Picasso has been set at auction in New York.
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Bristol have re-signed London Irish hooker Jason Harris-Wright.
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A shot was reportedly fired at a car outside a primary school in Liverpool as parents were taking their children inside, police have said.