In theatre, it was considered bad luck to wish someone good luck before a performance. By telling them to "break a leg!", that was reversed- by wishing them bad luck, you would bring good luck. It has become a theatre tradition.
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According to stage actors, it means "good luck". Wishing faux ill to someone is a way to bid them good luck without jinxing them.
Telling an actor "break a leg" before a performance is a reference to a superstition that is tradition in the performing arts. It is considered bad form to wish luck to an actor pre-performance, much as it is considered bad luck to mention the name MacBeth in a theater (references are made instead to his "Scottish play"). Strangely, this superstition runs counter to another classic encouragement, the slang expression "knock 'em dead."
In theatre, it was considered bad luck to wish someone good luck before a performance. By telling them to "break a leg!", that was reversed- by wishing them bad luck, you would bring good luck. It has become a theatre tradition.