Milestone Birthdays can be a lot of fun. One idea for celebrating a milestone is a roast. One of my favorite themes for a birthday roast is a memorial.
The first thing you will want to do is send out the birthday invitations formatted like an obituary. A cheesy black and white picture of a younger version of the decedent adds a touch of legitimacy to the document. If you or any of your cronies have a flair for creative writing this can be a very warm and funny tribute, as well as a keepsake for all attendees.
The location for the roast or memorial should be as somber as possible and decorated as such. Be sure to greet the guests in your with your most solemn and understated demeanor.
Just before the festivities begin have your pall bearers bring in the cake, unlit. Make it as realistic as possible and give the pall bearers the honor of having a place of honor once the cake is brought in and placed in the appropriately.
The roasters are your eulogists and your obituary will set the tone for what tack they take. If you want to make the guest of honor wildly successful than you will want to set that down in the obituary, If you want him to be a depraved soul who it will be difficult to find something nice to say, then that is something you want to include.
Liberties and poetic license should be the order of the day. The way the honoree met his untimely demise should fit with his interests or something somewhat unique to them. Most of us remember the Mary Tyler Moore episode where Chuckles the clown was killed by a rogue elephant while dressed as a peanut. What more could you ask for in humor or irony?
Another idea is using cap guns for a 21 gun salute. This could be used if the honoree met his end in some form of heroics. Friends and family could be bogus people from his fictional biography.
Additionally be sure to hand out black armbands at the door if folks did not have enough foresight to bring their own. Black crepe paper is a good cheap way to supply these. Black party hats with veils made of black pantyhose or some other translucent material can also be made.
A milestone birthday roast disguised as a memorial can be and should be a lot of fun. You will have fun planning it and producing it, and if done well it will be a birthday party that folks will talk about for years to come.