Compare Jay Gatsby and George Wilson in The Great Gatsby.
George Wilson and Jay Gatsby have both experienced the impossibility of the American Dream. Wilson has attempted to achieve the dream by working as hard as he possibly can at his small garage in the valley of ashes so that he might earn enough money for him and his wife, Myrtle, to be happy. However, he is essentially at the whim of rich men like Tom Buchanan, who promises Wilson his blue coupe again and again, a promise on which he never delivers. Then, his wife cheats on him with Tom and she is run over by Daisy (though Wilson believes it was Gatsby driving), and Wilson turns the gun on himself after he murders Gatsby.
Gatsby, likewise, at first tried to come by his fortune honestly, but apparently learned that he would never reach the level of wealth needed to woo Daisy by being honest. Realizing that the American Dream is merely a fantasy, he has turned to a life of crime, becoming a bootlegger—and perhaps engaging in even more serious offenses—and it is in this way that he has earned his fortune. However, one cannot necessarily say that he's achieved the American Dream when he's had to resort to crime in order to be "successful."
Though Wilson and Gatsby are different in many ways, both characters show the impossibility of achieving the American Dream. They are both manipulated by the Buchanans, and they both pay the ultimate price for trying to achieve their dreams: their lives. It is telling that Tom and Daisy are able to walk away from all misfortune while Wilson and Gatsby end up dead.
Though Jay Gatsby and George Wilson are an unlikely pair for comparison in The Great Gatsby, they actually have several things in common.
First, both know what it's like to be poor. It's true that Gatsby has left those days behind them, but he was just as poor as George--if not more so--at the beginning of his life.
Second, both love a woman they can't have. A poor Jay Gatsby loves Daisy, a woman who embodies what it means to be rich. He had no chance of being with her at the time they fell in love. A poor George Wilson fell in love with and married a poor Myrtle Wilson; however, he never really had her love. From their wedding day, she was discontent and dissatisfied with her husband--the one who had to borrow his wedding suit. Wilson had no chance to win her love unless he made money, which he didn't.
Third, both suffered heartbreak. Gatsby's was a lifetime of yearning and longing for Daisy, followed by a short interlude of love with her, and ending with a tragic denial of the love he thought they shared. Wilson's was a kind of ignorance that Myrtle was so unhappy, followed by the tragic discovery that she loved someone else (or at least was with someone else), and ending with her sensational death.
Finally, they were both victims of Tom and Daisy Buchanan's careless lifestyle. Each of them lost their loves as well as their own lives to this self-absorbed pair, with various tragic moments in between.