The prime minister said she enjoyed watching "Holiday Inn" over the festival period, describing it as a "real holiday classic".
Some social media users queried the choice, given the film includes white actors pretending to be black and has been criticised for its racist undertones.
In the infamous scene, Crosby performs a song called "Abraham" while wearing dark face paint.
Actors playing the staff of the Holiday Inn hotel, including the orchestra, are also in blackface, while all the guests are white.
Some televised versions of the film now omit the offensive scene.
Ms May told Politico: "My favourite festive film is ‘Holiday Inn’ with Bing Crosby — it gave us the original version of ‘White Christmas,’ and is a real holiday classic."
In one part of the film, after applying the dark makeup to her face, another character says: “For a month and a half I’ve been dreaming how pretty I was going to look tonight. Well, here is my punishment for thinking so well of myself.”
Other cabinet ministers also revealed their Christmas favourites.
Michael Gove, the environment secretary, said: “It wouldn’t be Christmas at the Goves without ‘Whisky Galore,’ ‘The Sound of Music,’ and ‘It’s a Wonderful Life.'”
The latter is also enjoyed by Matt Hancock, the health secretary, who said: "“My favourite Christmas movie by far is ‘It’s a Wonderful Life.’ It’s a story about what really matters in life, and a real tear-jerker.”
Amber Rudd, the work and pensions secretary, said: "“It has to be ‘Elf,’ with the whole family. And we all scream loudly ‘Santa!’ with Will Ferrell when he does. Just so good — schmaltzy, but funny too. I love it!”
The government chief whip, Julian Smith, joked that watching "Home Alone" reminded him of lonely weekends in Downing Street in recent weeks as he attempted to convince Tory MPs to back Ms May's Brexit plan.
He said: "Just polished off ‘Home Alone,’ which has reminded me of seemingly endless weekends on the phone at No 9 over the past few months. And looking forward to ‘Miracle on 34th Street’. It’s a family favourite, but has particular resonance for me this year.”
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