It sounds like it would be an easy thing to develop a culture of fun, play and humor in the workplace; and in some ways it is. But there are some critical issues that have to be considered along the way.
The most essential is to have the support of the leader(s) of your organization. The leader has to, at least, give his/her okay that fun is an acceptable part of the culture; that s/he will endorse fun by allocating time for those who are the "court jesters" to plan and implement activities; provide financial support; and attend and participate in the events (and encourage others too as well).
In some instances the leader may take a much more active role in the planning process and may even create an infrastructure to advance fun in the workplace.
In return, the leader must be kept in the loop about fun programs that are afoot; has his/her calendar checked before the event is scheduled to be sure that the event is scheduled for a time when s/he is available to attend; is thanked publicly for his/her support, etc.
Remember, fun is not an end to itself. It is a means to such notable outcomes as breaking down organizational and personal barriers; team-building; reducing stress; increasing productivity; etc. Consequently, there is a strategic component to fun in the workplace that cannot be lost sight of.
Here is something Dr. Ilene Rockman wrote about the importance of leadership in promoting fun in the workplace [Reference Services Review, Volume 31, No. 2, 2003, 109-110]:
"When we recognize the importance of humor, fun, teamwork and camaraderie, we send a powerful message to our employees and patrons. We show that we value people as well as their work, and are willing to take the time to boost morale, esprit de corps, and communication...When administrators show their respect for fun activities, they also show their flexibility, appreciation and respect for their employees. They receive, in return, loyalty, productivity, and more than they ever imagined."
Amen!
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