How to Marry a Billionaire: A Christmas Tale (2000)

Three broke men, a sculpter, an obsessive compulsive teacher, and a stupid actor desperately want to be rich. Someone lends one of them their mansion and cars while they're off on their Christmas vacation. They then pretend to be rich so they can get rich girls, as they have had bad experiences with women leaving them for richer men. But every farce has got to end sometime...