You don't have to be Shakespeare. You just need to have a plan, execute it, get in, get out. (Think of it like invading a small country.)
Don't wing it, don't overstay your welcome, and don't piss off the locals. Yes, confidence and delivery matter. (More on that here.) But the most important element? The plan itself. You need to have the toast written out, and that starts with a template. Like this one.
Every good best man toast has four components:
2) Funny (but not snarky) stories about the groom
3) Glowing words about the bride
4) Upbeat Conclusion.
No need to over-think it. If you stick to those 4 components, you'll be fine. How long should it be? Anywhere from 45 seconds to 5 minutes. If it's less than 45 seconds it looks like you didn't give it any damn thought. If it's longer than 5 minutes, then no matter how charming or brilliant you are, you'll lose your audience. And, frankly, this is not the moment to try to impress everyone in the room with your accomplishments and brilliance.
A note on mechanics. You should have it mostly memorized, but also print it out and have it in front of you. Go one step further and print out a copy in a cartoonishly large font. Make lots of little paragraphs. Chunk it up. That way if you lose your place when looking up at the crowd--which you should be doing, frequently--you can quickly find it again. And double-space the son of a bitch.
Okay, onto the content itself. We'll walk through each section, blow by blow. The good news: two of them are super-easy. The intro and conclusions are paint-by-numbers; you just need a couple of warm-and-fuzzy gems.
If you're feeling gutsy, and if you trust your instincts and public speaking chops, you can have a tiny moment at the beginning where you humorously comment on something that just happened that night. This adds flavor and spontaneity, but it needs to be quick and in good taste. (This part's optional.)
When you start, don't assume people know who you are. Many have no clue. But avoid opening with the lame, "For those of you who don't know me, I'm ......." Everyone else speaking will say the same exact thing, so try and separate yourself from the herd. Instead, start your speech with how you met the groom. It should be both factual and funny. Start with the fact, then pivot into the joke. Like this:
"I met Jason when we shared a cell together in Folsom prison." That's the fact. Then you pivot into... "Back then, his ‘girlfriends' were named Frank and Bill and had him pick up the soap, if you know what I mean."
Okay, just making sure you're paying attention. This violates two rules that you should have learned from this article: 1) No humor that will upset Grandma; and 2) no mentions of ex-girlfriends, not ever, under any circumstances.
Still, that example should give you the idea. Just start with "I met (groom's name) (here)", pause, then you give a kicker.
So, more realistically:
"I met Charlie when we were roommates at Florida State." Fact, then pivot into a quick little anecdote that you later leverage... "In college, he was the worst cook I'd ever seen, maybe that the world has ever seen. When he made pasta, he used ketchup as sauce. Not kidding. Ketchup."
Not laugh-out-loud funny, obviously, but mildly amusing and the trick is to later use this in reference to the bride. (You'll see.)
For Sections 2 - 4, click here for the full article...