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)