As is often the way with language, there seems to be no definitive answer as to the true derivation of this term.
Below are offered some suggestions:
1) Lincoln / Wilkes Booth Injury
From Dave Wilton’s Etymology Page : http://www.wordorigins.org/
Superstition against wishing an actor Good Luck! has led to the adoption of this phrase in its place. Popular etymology derives the phrase from the 1865 assassination of Abraham Lincoln. John Wilkes Booth, the actor turned assassin, leapt to the stage of Ford’s Theater after the murder, breaking his leg in the process. The logical connection with good luck is none too clear, but such is folklore.
There is no evidence, however, to suggest that this is the true derivation, and since the earliest usage of the phrase dates to the 1920s, there is much to suggest that it is not. The best that can be said is that the origin is unknown.
2) Hals Und Beinbruch
A DICTIONARY OF CATCH PHRASES (see below) suggests that there may be a connection with the German phrase Hals und Beinbruch, an invitation to break your neck and bones. The German phrase is used by aviators and is equivalent to the English phrase Happy Landings!. Both phrases arose about the same time, the early twentieth century, but the connection between the German aviation community and American theater is unclear, so they may be unrelated.
A Dictionary of Catch Phrases; Eric Partridge; edited by Paul Beale; Scarborough House; 1992; ISBN 0-8128-8536-8. Contains excellent information, but unfortunately suffers from an odd alphabetization system, the lack of an index, and few cross references, all of which makes finding the phrase you want difficult at best.
A DICTIONARY OF SLANG AND UNCONVENTIONAL ENGLISH, published some eight years before the above, does not list the theatrical meaning. Instead, it lists an obsolete meaning of “to give birth to a bastard child,” from circa 1670.
A Dictionary of Slang and Unconventional English, 8th Edition; Eric Partridge; edited by Paul Beale; MacMillan; 1984; ISBN 0-02-594980-2. A superb source that focuses mainly on British slang, but which is also useful for Americanisms.
For more interesting word origins, visit Dave Wilton’s Etymology Page : http://www.wordorigins.org/
3) Bending the Knee
From : http://www.footlights.com/art7d.html
For contemporary English-speaking theater people, the ritual greeting reflects that calamitous 42nd Street production, “Break a leg.”
However, the rather terrible curse may have had a more benign origin. Much earlier in stage history, when superstition had a less frightening hold on the craft, actors and their followers used a more gracious greeting: “May you break your leg,” by which it was meant that the evening’s performance would be of such grandeur that the actor would be obliged to break his leg – that is bend his knee – in a deep bow acknowledging the audience’s applause.
4) Getting Onto the Stage
From : Josh Pritchard – firstname.lastname@example.org
Evidently, in the days of early vaudeville, the producers would book more performers than could possibly perform in the given time of the show – since “bad” acts could be pulled before their completion… so, in order to insure that the show didn’t start paying people who don’t actually perform, there was a general policy that a performer did NOT get paid unless they actually performed on-stage. So the phrase “break a leg” referred to breaking the visual plane of the legs that lined the side of the stage.
i.e. “Hope you break a leg and get on-stage so that you get paid.”
5) Outsmarting the Sprites
From : http://members.aol.com/morelandc/HaveOriginsData.htm#BreakALeg
Meaning: A wish of good luck, do well.
Example: Break a leg in your game today.
Origin: “Break a leg” is sourced in superstition. It is a wish of good luck, but the words wish just the opposite. It was once common for people to believe in Sprites. Sprites are actually spirits or ghosts that were believed to enjoy wreaking havoc and causing trouble.
If the Sprites heard you ask for something, they were reputed to try to make the opposite happen. Telling someone to “break a leg” is an attempt to outsmart the Sprites and in fact make something good happen. Sort of a medieval reverse psychology. Of course it has became a popular wish of luck for theater performers.
6) Take A Bow
From Gary of Players Ring :
I’ve run into considerable debate over the origin of this one. My favorite (having understudied a few times) is that it came from the understudies telling the primaries to “break a leg” enough times that it came to be considered bad luck if they didn’t say it. A more likely origin is from Shakespeare’s time when “to break a leg” meant to “take a bow”.
7) Break A Legend
From David Scears :
In the nineteenth century theatre, when it was the norm for actors like Keen, Tree, and Irving to be actor managers. They would perform a role many times and for many years. When a new actor would take over a particular role that had become closely associated with one of these legendary actors he was told “break the legend”. Over time this gradually got changed to “break a leg”.
8) Greek Stomping
I always heard that in the Greek times, people didn’t applaud–they stomped for their appreciation. So if they stomped long enough, they would break a leg.
9) Elizabethan Stomping
From Mike Mesker:
I heard that the term originated during Elizabethan times and that instead of applause the audience would stomp their chairs, and if they liked it enough the leg of the chair would break.
10) Compensating for Injury
From Jing de Leon:
The first time I heard this phrase when I was 12 years old in Manila. I asked the director what it meant and where it came from, he said (with details of time and names, I don’t remember any more) there was lead actor on a play who broke his leg an hour before curtain time, all the cast members learned about it, and he still went on despite of his condition. All the cast members did their best performance that night, because everyone was worried that the audience might notice the broken leg, as a result they got the best review the next day.
11) Australia: ‘Chookas‘
The Australian term for “break a leg” is “chookas” (pronounced chook-as).
M Stephen Armstrong contributed the following explanation:
There is a placard at the sign in desk, stage door of the Princess Theatre in Melbourne, which relates the following etymology:
“During the early days of J.C. Williamson’s dominance of the theatre scene in Australia. In the early 1900s chicken was regarded delicacy and could cost a good weeks wage . As most shows paid fees depending on the box-office take, a full house meant that the performers would be able to afford a chicken meal. The cry ‘chook it is’ was shortened to ‘chookas’, and eventually used by performers to wish each other a successful show regardless of the number of people in the auditorium.”
12) Opera Singers
Opera singers use ‘Toi Toi Toi‘ which is believed to be an onomatopoeic representation of spitting three times (believed to expel evil spirits)
Thanks to Adrienne Redd for help in locating definitions 1 to 5 and to the folk who’ve taken the time to email in their own suggestions.