Retirement parties are a great way to honor a person's years of service. To make a retirement party a success, keep the mood light and humorous. Skits about the retiree's experience with the company and life in general are a great way to keep things fun and nostalgic.
Enact a situation that the retiree may have experienced at work. Have co-workers take part in the skit, and make sure that the skit brings out the personality qualities unique to the retiree, in good fun. The skit can focus on the retiree's skills, but the audience will most remember skits that demonstrate what is cherished about the retiree. Consider carrying out skits that illustrate the retiree's relationships as well.
Re-enact well-known, embarrassing situations that the retiree has been in. These need not be limited to situations that occurred at work, although you should certainly include them. If there are well-known, endearing but embarrassing facts about the retiree's life outside of work, consider including them. If possible, include the original people involved in the embarrassing situation as actors. Consider exaggerating the situation to make it even funnier. Even party guests who weren't originally aware of the embarrassing facts will enjoy them.
Write a rap about the retiree's life. With rhyme and rhythm, summarize key points in the retiree's life: the names of his parents, key accomplishments and/or embarrassing stories from college, key places where the retiree worked, funny stories from those places, and anything else that will be entertaining. Get one talented performer or multiple people with acting skills to bring the rap to life. If possible, involve members of the audience.
Make a video collection, using real footage or filmed, reenacted events, of the retiree's time at work. Add dramatic music, intersperse it with commentary and short film sequences to make it funny, and cut it dramatically to make the collection more theatrical and engaging. Your guests will appreciate the effort that you put into it, and will enjoy the chance to watch little films about the retiree's life, created from your point of view.