I remember my 2nd speech from the Humorously Speaking manual was close to a disaster. I got a few awkward smiles at best and I thought "f*** why did I pick this manual?"
Then I reminded myself - it's because I love to listen to funny speeches or speeches that have incorporated elements of humour. I want to do that.
So I learned how.
Here are some things I've learned from giving humorous speeches and other speeches that had elements of humour in them
It's easy to laugh at or with (depending on your goal) someone who seems confident. So I just act more confident than I am when I give a humorous speech. If you make a joke, which doesn't land just move on.
Looking back over my 5 speeches in this advanced manual, I was probably faking my confidence for the first 3, then only somewhat faking my confidence in the last 2.
Present jokes tailored to your audience. If I made 90s music references to a bunch of people who are 50 or 60 years old, then they might not fly. (This is working with the assumption that people are most familiar with/fond the music they grew up with).
Know your audience
In one of my last speeches for Humorously Speaking, I gave a speech on "My Road to Recovery" on Tinder. First that Toastmasters group were mostly in the 25-35 year old range, so most people would've either been using Tinder or had friends who use it.
I also made references to life in Sweden, here are some excerpts from the speech:
Online dating is one of the best ways to meet people in Sweden especially in winter. You don’t even have to leave the comforts of your own home to meet beautiful women and handsome men to go out on dates with.
The above joke was supposed to work two ways. Firstly Sweden is very cold in winter. Second it's common to live by yourself in Sweden until you met your special someone.
I met up with a guy at a bar. Oh, he’s not as cute in real life - I guess that’s to be expected on an app like Tinder. “Nicola don’t be so shallow.” So, I stayed.
5min in, I realised I would rather give up meatballs and IKEA forever than keep talking to him.
This joke was again tailored: first, Tinder has a bit of a reputation for having people "oversell" themselves or at least not depict themselves in a truthful light. Second, IKEA is a very popular store to go to (lots of apartments here are furnished with IKEA stuff).
The element of surprise
Being able to lure your audience into an idea and then surprise them is very useful in giving funny speeches (or just speeches in general for that matter).
Usually to do this, you would tell a story or do some sort of "set-up".
Here is the intro from another speech I gave in my Humorously Speaking manual
I stand here before you today to profess my love. I don’t want to embarrass him by drawing attention to him in front of all of you. But I think you need to know a few things.
He’s always there for me. He provides hours of entertainment. Lastly, if I had to run out of a burning building - he’s the first one I’d grab.
Today, I present to you - my cellphone.
You may think - wow Nicola, how heartless can you be? What if your boyfriend was in the building?
Well, the thing is, he has legs, my cellphone doesn’t.
FWIW, my boyfriend was in the room (this helped with the set-up as people may have actually thought I was talking about him).
Assuming your audience is somewhat familiar with current events, then making jokes about what's happening in the world these days is bound to be a hit.
Nowadays some ideas include Trump (if you don't like him and are speaking to an audience who don't like him) and twins by Beyonce.
However, I would be careful here. I would not make fun of or incorporate jokes about any bad current events (e.g. a death, natural disaster). Also, when it comes to political stuff (e.g. Trump), tread carefully. In situations like this, I think there's a fine line between being funny and insightful & insensitive and ignorant.