Most newsletters are boring, uninspiring and because of their dry content, rarely read. Funny newsletters can catch people's attention, make the newsletter memorable and relay important information to the people who need it.
Pull an Orson Welles on readers. Before TV shows, people listened to dramatic readings of scripts on the radio. In arguably one of the most infamous moments in US radio history, famous actor Orson Welles narrated in an urgent voice a series of simulated news bulletins that aired over the Columbia Broadcasting System radio network. The announcements contained every trapping of an emergency news broadcast, but were based on H.G. Wells’ novel War of the Worlds, about a space alien invasion. Welles had listeners all over New Jersey and elsewhere believing for days that Martians had landed and were destroying New Jersey.
Depending on the typical subject and readership of the newsletter, think of something totally believable but totally outrageous. The next newsletter should admit that the prank letter was fake. As with any prank, make sure no feelings will be hurt after you reveal the hoax.
Write a caricature of a group or individual of which your readers are familiar. For example, write the company newsletter as if it were the monthly letter of a leading competitor, only add a few touches to make it ridiculous. Include any jabs the other company has made against your company. Also include inside jokes about the other company that your co-workers have already made in discussions about the competition. The same warning goes as for the hoax newsletter idea: make sure it stays lighthearted in case a member of the other company gets a hold of the letter. If any serious slander is issued in the newsletter, it could mean a libel lawsuit.
Inside Joke Catalog
Speaking of inside jokes from your group, this is the best source of humour for a group newsletter. Turn the newsletter into a catalogue of the best inside jokes made by members this year. Some members probably never got the full story behind each joke. If there is leftover room in the letter, include interviews from members explaining how the funny moments or jokes came about. If it’s an online newsletter, include Internet links of any video footage of funny or embarrassing moments. Make sure to get permission from each joke participant to include their inside joke in the newsletter.
Send copies of the newsletter where they do not belong. Mail the volunteer choir newsletter to a heavy metal magazine and ask to be included in their next issue. Get a list of names of the spouses or close friends of each member of the group and write a special edition of the newsletter for them, with minor embarrassing truths about group activities, even individuals in the group. Make sure not to do anything too inappropriate with the newsletter’s content.