Why did both the Cynic philosophical movement and the hippie movement (two very similar movements) fail? I believe the answer is that they both failed to clearly convey their message. Certainly a message was received and absorbed by society, but given the nature of the two movements, an absorption of some of their ideals by society would seem to me to speak more of a failure than a success.
The nature of what the two nearly parallel philosophies sought to convey is such an enormous issue—since the two philosophies speak to the entity of society itself—that proper communication of the philosophy to the masses would have been crucial to its success.
Assuredly, both movements were subject to hijacking by various social and political movements almost as soon as they had begun, as this is the case with all grassroots movements and revolutionary philosophies. Specifically in the hippie movement, everyone with an agenda most definitely hopped onboard and implanted their ideals into the movement as if those ideals were somehow compatible with the initial philosophy. For example, certainly no one would dare argue that a true criticism of the nature of society is somehow compatible with an economic or political philosophy, since both economy and governance are two of the pillars of society itself. How could one argue for a new economic or political philosophy and dare criticize the nature of society? That would be like arguing against breast-feeding with the right tit and suggesting the left is somehow more perfect. Indeed, it would have been hypocritical for a hippie who was a true Cynic to attach their self to such things, which would have been in direct opposition to their ideals.
Trying to prevent various groups who each have their own agendas, including other governments, or the powers that be from co-opting any movement has always been a problem for any grassroots movement, and the only answer has always been to guard the movement, which is typically done either through centralized control (a bad idea for a number of reasons) or through a commonly understood philosophical ideal. For numerous reasons, the latter is usually the way it is done (basically because, unlike a man, you cannot kill an idea), but such a method has its weaknesses which are always taken advantage of.
I believe the solution to this notable problem is properly sufficient and efficient communication of the movement's philosophical ideal. Unfortunately, the lack of such communication has always been the downfall of any worthy movement.
By sufficient, I mean that the message should be appealing, desirable, and persuasive, and that it should be delivered in such a manner as to be nearly indestructable or tamper-proof. The goals and ideals of the movement should be presented much like food for the masses. It should look appealing, smell appealing, and if possible taste appealing, so that it is found to be desirable to a large portion of people. Presentation is really everything! For example, if one is criticizing society itself, then it would not only be a good idea to point out the insurmountable problems of society, but to also show, in an attractive manner, the most obvious benefits of the alternative.
Obviously any concepts which are counter to that of society are not going to look very appealing, since all people have been born into and weaned on their society, and it is all they know, so the sufficiency of the message should not only be targetted at making the alternative itself look attractive, but it should also be focused on changing the way the individual and the masses actually perceive their choices. In other words, it needs to be made attractive not only to their eyes, but also the very way in which they think about it must necessarily be transformed, if possible, before the actual perception is even had (making the way things are currently done look ugly helps too).
By efficient it is meant, that the philosophical ideals and/or goals of the movement must be clearly, concisely, and thoroughly expressed in a manner which is unmistakable to the overwhelming majority. By clear it is meant, that one should really have to either go out of their way or be rather dense to miss the point. By concise it is meant, that the message should be wrapped up in as few terms which can be misinterpreted as is possible, and in which the masses can easily understand it. Finally, by thorough it is meant, that not only should the arguments against a particular way of doing things be heard loud and clear, but the alternative should be understood just as clearly, and should be just as readily discernable as any criticism. The message should be capable of delivering the entire desire behind the movement and of bringing it into fruition, from start to finish, in as few words which are able to be misinterpreted as possible, and delivered in such a way as to be most efficient.
Such an efficient delivery requires two tools: individual representation and mass communication. Besides being made to look bad and ultimately falling prey to co-opting, the hippie movement lacked an adequate means by which to communicate its message to the masses. The social order was able to suppress and twist the message because it held a far greater and more efficient means of mass communication in its hands. To get around this, a movement would have to either take advantage of new means of mass communication which are not yet wholly controlled (such as the Worldwide Web currently presents itself) or use as extensive arsenal of tools of mass communication such as books, films, music, art, posters, etc. Something like handing out copies of films in mass would seem the most efficient means by which to deliver a sufficient method in today's world which, unfortunately, was not an option for the 1960s hippie movement.
Unfortunately, another problem which any movement designed to criticize society undoubtedly runs up against is the use of tools which society built in order to aid in the acheivement of its goals. Such a practice is inevitably accused of hypocrasy, but the means by which to counter this accusation is to make clear from the start (perhaps in the original message itself) that in order to free another from their prison one must physically walk into the prison and release their shackles. In other words, if they are imprisoned by the use of indoctrination through mass communication, it is necessary to use such tools of mass communication to initially free them from their indoctrination. You cannot reach out to someone in the virtual reality of the social order unless you go there yourself.
And so, I am convinced that the hippie movement was a failure due to two things: it failed to sufficiently and efficiently convey its message and it was co-opted nearly from the get-go. I am fully convinced that the movement was initially grassroots and uncorrupted, but that it was taken over by extremist elements who had their own political agendas almost as soon as it got rolling, and then it was ultimately squashed by the ruling social order, who, more than likely, were also responsible for the initial co-opting and likely used controlled opposition as a means by which to end a legitimate movement of the people – such is the case throughout history. Afterall, if you make a movement look threatening or unattractive through the use of controlled opposition and mass disinformation before the overwhelming majority are awakened to this new way of viewing things, the people will naturally reject the movement.
If we want to see things change we need to learn to communicate better. We need to become more sufficient and efficient in our messages. We need to jealously guard the core philosophical principles of a genuine grassroots movement. We must understand the political, sociological, psychological, and military tactics which have been used throughout history to crush genuine movements of the people. We must understand what makes our fellow brothers and sisters "tick". We must understand the art of man-herding (as Socrates called it), take tips from past movements, perfect the implementation of centralized leaderless movements (take a tip from the Christians, who's leader was already dead and therefore unable to be killed), insist upon peaceful resistance and study the techniques of individuals such as Ghandi, Christ, Martin Luther King, Jr., Thomas Paine, etc. Because peace, freedom, and brotherly and sisterly love for all mankind is only one well-organized and intelligent communication of an idea away.
No one can fight the system, which is nothing more than an idea itself, in action, unless they fight it with an idea which is also placed into action by the people.