Cholo's are usually fat, so they are afraid of falling, because they can't get up. So when you lean like a cholo, it is an expression that you say to fat people (usually hispanic) meaning that they are about to fall, therefore they need to put their elbows up and move them side to side like a cholo so that they can keep balance, and stay upright.
Lean like a cholo Example:

Person A: "Woooah!"
Person B: "Watch out! You're leaning like a cholo!"
Person A: *puts his elbows up and moves them side to side*
Person B: *phew* :-)
by Daviel May 9, 2008
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