Start out by telling him you have two stories and say that if the first doesn't make him laugh, the second will.
Story #1
Two guys are walking down a road when they come across a red brick. One says to the other, 'Betcha fifty bucks I can throw it up and it won't come back down.' He takes the bet. Brick goes up, down, and the guy pays $50. They keep walking and come across a yellow brick. Same thing: 'Betcha $50 I can throw it up and it won't come back down' Guy takes bet. Brick goes up, down, and the guy pays $50. They keep walking when they come across a green brick. "Betcha $200 I can throw it up and it won't come back down." Guy takes the bet. Brick goes up, never comes down, so the guy gets $200.
End of story.
At this point, he'll be like, 'What the heck?!' So tell him the next one.
Story #2
A man and a woman are in an airplane. The man is smoking and the woman has her pet chiuahah on her lap. She says, 'Sir, you're not supposed to be smoking.'
He blows smoke in her face and says, 'whatever.' She says, 'If you don't stop, I'll sic Fifi on you!' He says, 'Whatever'
She does, and Fifi goes crazy, ripping his clothes. He says, 'What the heck, Lady?!'
She says, 'If you don't stop, I'm throwing your cigarette out the window!' To which he replies, 'If you do that, I'm throwing your dog out the window!' She takes his cigarette, throws it out the window. He takes her dog and throws it out the window. They both sit fuming for half an hour until they look out the window and see Fifi sitting on the wing of the plane. Guess what's in Fifi's mouth?
To which, he'll probably say, 'The cigarette, right?'
Then you say, 'NO! The green brick!'
Hahhahaha. I love that joke. It takes a while to tell though, so make sure you have the time. It's a gar-un-teed winner!
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