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Jamaican Bobsled Team 

A term used to describe a situation that is possible, but unlikely to happen. Popularized by the tv show Glee.

Based on the 1988 Winter Olympics team who fell short of winning any medals but did surprisingly well.
"What do you think the chances are that Jennifer will say yes if I ask her to go out with me?"

"Jamaican Bobsled Team, dude..."
Jamaican Bobsled Team by P Banger February 15, 2010

Jamaican Jerked 

To receive a hand job after an intense sunburn on one's genitalia.
After lying naked in the sun for hours, John got a sunburn on his dong. He went home and his girlfriend Jamaican Jerked him with Aloe Vera.
Jamaican Jerked by Rufioau January 18, 2009

Jamaican Hand Grenade

Nickname give to Red Stripe (TM) Beer, refering to the bottle's somewhat unique barrel shape with a short neck. Also used in reference to potencey of the beer.
"Hey man, toss me one of them jamaican hand grenades" ; "Those jamaican hand grenades kicked my ass last night" ; "One of those jamaican hand grenades went off in my head"

Jamaican Circle Jerk 

A highly localised twist on the traditional circle jerk, this variant requires all members of the circle jerk to have full bottles of Red Stripe Beer lodged in their anuses. The idea is to absorb as much Red Stripe through the rectum, as possible before climaxing.
- "Yo, Brent, you coming to the Jamaican Circle Jerk tomorrow?"

-"Yeah, but first I gotta pick up a case of Red Stripe"

Jamaican Pirate 

The "Pirates" Faction from the 2008 PS2 game Mercenaries 2: World In Flames. They are incredibly stereotyped Jamaican gangsters who are hilarious to wind up, as they come at you, not wit a gun, but with a rocket launcher.
Jamaican Pirate: "Don' use de gun, use de rocket launcher!!!"
Jamaican Pirate by Greenhoof June 10, 2010

Jamaican clambake 

Smoking pot in the bathroom with the shower steaming hot.
When I get home I’m gonna get a nice Jamaican clambake going!
Jamaican clambake by Vtblaster December 3, 2018