A term used to describe a hundred dollars; because the twenty has a picture of Andrew Jackson on the front, five of them would equal a hundred dollars. Thus, The Jackson Five. Similar to calling a hundred dollar bill a Benjamin.
Bouncer: I'm sorry, I can't let you in.
Man: But I have some friends who can vouch for me. The Jackson Five, perhaps you've heard of them? (Hands the man 5 twenties)
by Lord Addius May 5, 2007
In poker (namely Hold 'em poker), when your hole cards are a Jack and a 5, especially when the cards are clubs and/or spades.
Johnny's got Jackson Five, and folds quickly.
by withheld234323 January 3, 2006
A codeword for a joint of marijuana, intended for five people

OR

just a really big joint of marijuana.
We went to the pub with the gang the other day, rolled a jackson five and got sweety high...
by derS August 10, 2005