OK - your speech is underway. You've opened well and introduced yourself properly. The audience are loosened up and on your side. They are ready to laugh. They'll be expecting you to poke fun at the groom so don't disappoint them. But before you launch into a full frontal assault, consider the following points:
1. Is it a joke or an insult?
If you're worried that your material could be taken either way don't leave the audience guessing. Give them advance warning that a roast is on the way, and you're about to push the boundaries …
"As best man, it now gives me special pleasure to provide a candid, unflattering insight into the people whose marriage you have all just witnessed."
2. For a joke to work, people need to know what you're talking about.
The wedding guests will laugh freely at quirks and eccentricities that are widely recognized in the groom. Consider his appearance, character traits, career, hobbies and past. Your portrait is expected to be an exaggeration, but nonetheless it must be based on fundamentally familiar truths about the groom. For example:
If he's a notorious couch potato …
"Now he's married, Paul can really let himself go … oh, he already has!"
If he's a computer game addict …
"Now, I know Paul's pledged that this wedding is a fresh start for him - he's going to leave behind his old, computer-obsessed bachelor life and start from the beginning. No more obscure PC game references, no more techy jargon. What we'll see from today, he assures us, is Paul 2.0."
If he's an estate agent …
"I hope you realise Linda, that in his job, Paul is used to making assets sound like they're much bigger than they actually are. I just don't want you to be disappointed on your wedding night, that's all."
3. It's a wedding. Remember to connect your gag with the occasion.
Wading in with punch-lines and put-downs can leave your speech sounding too much like a stand-up routine. You need to find a way to plausibly lead-in to your joke, while remaining mindful of the special occasion at all times. A neat trick is to cue your joke with a statement about marriage, a wedding day observation, a quip about the ordeal of being a best man, or a comment about writing the speech. Thus:
If the groom has a rep for being tight-fisted …
[Wedding day observation] "This has truly been a day to remember!"
[Gag] "The day Paul bought the drinks."
If the groom is a gambling man …
[The ordeal of being a best man] "I think all went well this morning in getting Paul ready for his big day. The condemned man ate a solid, hearty breakfast and arrived at the church sober and on time."
[Gag] "My one disappointment would have to be failing to arrange his last request as a single man - to put the honeymoon fund on an Arsenal home win this afternoon."
If the groom is football mad …
[Statement about marriage] "I think Paul sees marriage as being very similar to his beloved football - he's totally committed, and wants to score every Saturday, change ends at half time and play away half the year.
[Gag] "The trouble is, Linda is predicting that he's going to suffer from a serious groin injury if he does."
If the groom is an only child …
[Comment about writing the speech] "In preparing a speech like this it's often useful to talk to the subject's siblings who will have a different perspective on the star of the day."
[Gag] "But Paul's an only child… his parents decided to stop while they still outnumbered him!"
4. Seize every opportunity to send yourself up.
Self deprecating humour will get the audience rooting for you. So, if you're making a joke about the groom and can send yourself up at the same time, all the better!
If the groom is known for his dubious fashion sense …
"Prior to meeting Linda, Paul had many men in his life - Gianni Versace, Giorgio Armani, Yves Saint Laurent to name just three."
5. Put yourself in the story.
If you're relating genuine first-hand experience, your joke or story will always sound more convincing and amusing.
You could recount your first impression of the groom, explain how you met, how long you've know each other or why you think you've remained such good friends. Delve into your mutual past for an amusing tale or a humorous observation. There's bound to be at least one embarrassing or outrageous memory you can draw on.
If you went to school with the groom …
"You can draw your own conclusions on whether Paul always put the effort in at school, but he only used two pens between the first and sixth form - one to clean each nostril."
If you're a work colleague …
"I apologise if this speech contains no factual information or refers to things that haven't happened, it's just that I cribbed most of what I'm about to say from Paul's LinkedIn profile."
If you lived with the groom …
"I'm not sure what Paul's like now, but when we lived together he used to transfer food onto dishes instead of eating his dinner straight out of the saucepan - and he'd wash up after meals instead of putting all the things in together at the end of the week, when you take your bath."
6. Connect your ideas together.
If you have a number of amusing character traits you wish to convey, it's better to get several out in one go in a nicely crafted bundle.
In the example below the groom's interest in golf, poor driving record and his law-breaking past have been acknowledged in one fell swoop.
"For those of you here that have only just met Paul, the people here on Linda's side, I do envy you - because the pleasure of getting to know Paul lies ahead of you. And just to ensure that first conversation or encounter goes well, I recommend that you steer well clear of the following list of contentious subjects: Paul's A-level results, Paul's golf handicap, the number of points on Paul's driving license and finally, Paul's whereabouts the day all those mountain bikes went missing in Newport. Steer clear of those and we'll all have a good time."
This paragraph shows how several of the groom's interests can be woven into one gag. It provides a useful template; just substitute the details for things relevant to your groom's interests …
"Paul paid me the ultimate compliment when he asked me to be his best man. Although I will admit that it came as a huge surprise to be picked ahead of the Manager of Homebase in Chichester, the Editor of Gadget Magazine and a handful of West Sussex bike shop owners....And I learnt through Twitter Bill Gates thought he was in with a shout."
And here's another example …
"For those of you who don't know Paul, he has never been lucky in doing things right the first time. It took him 7 tries to pass his driving test. 5 applications before he got membership to a golf club. 3 tries at his 25 yard swim test. And 2 attempts to convince the doorman he was sober on his bachelor party night. But today as you all saw he gained his marriage certificate with flying colours, on his first attempt!"
7. What if the groom's past and personality really do leave you short of best man speech material?
If the groom has led an unusually sober and uneventful life to date, don't panic. There are other avenues for generating humour:
You could simply acknowledge your predicament …
"Ladies and Gentlemen, this is quite unusual for me. Here I am with a room full of people waiting to listen to my every word, and for once I can't think of anything to say. Paul, I do wish you were more interesting."
If you can't think of anything funny about the groom, focus on the newlywed's romance and relationship for giggles. Can you turn their meeting or their growing love into a source of humour?
"When Linda finally agreed to go out with him, to try and impress her, Paul took her to the most expensive restaurant he could afford. And the evening went well, he made her laugh so hard… she dropped her fries."
"Linda had a profound effect on Paul within weeks of meeting him. In fact, it was after just one month that she summed up his bachelor lifestyle in one word - 'over'."
8. Don't be concerned about stretching the truth a little.
The truth on its own is rarely entertaining and today you have the clown's traditional license to bend it to suit your needs. You won't be judged on factual accuracy, what counts is the entertainment value of what you say. Is there a courtship incident you could put a spin on? Is there something funny you could say about the marriage proposal, the groom's first time meeting his future in-laws, or the happy couple's marital hopes?