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Movies like Jackson (2008)

Donald (Barry Primus) promises Sam (Charlie Robinson) the best day of his life. This seems unlikely, given they are both homeless men mired in the bleak landscape of Los Angeles' Skid Row. Moreover, the source of Donald's optimism is a mere $20 bill (called a "Jackson") which he bummed off a passing businessman (Steve Guttenberg) earlier that day. But Donald vows that with it, they can do anything, and drags a reluctant Sam off in search of adventure.