For the purpose of this question, we'll define the American dream as the idea that anyone can start out poor, and rise to become rich through hard, honest labor.
With that definition, here are three criticisms that can be drawn from The Great Gatsby:
The American dream does not work for everyone. George Wilson has done hard, honest work for many years since his marriage, but is in the same economic and social class as when he began. He lives in the Valley of Ashes. His wife Myrtle is discontented with their life, and has an affair with a rich man (Tom) to enjoy the good things in life. George finally plans to move out West with Myrtle to get her away from her lover (and to pursue the American dream there?), but she is hit by a car before they can leave.
The rich are not any happier or morally better than the poor. This is seen from the decadent, foolish behavior of the guests at Gatsby's parties; the excruciatingly un-fun party given by Tom and Myrtle at the apartment where he keeps her; and Tom and Daisy's tortured lives.
The new rich are not really accepted or admired. Gatsby is an example of a newly rich person. He gives lavish parties, and everyone loves to come to them. Once Gatsby is killed, though, Nick cannot convince any of the former partygoers to attend Gatsby's funeral. They are all too busy with trivial things, or "don't want to get involved." It becomes obvious people attended Gatsby's parties just for the good time they offered, but did not respect Gatsby or consider him one of them.
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