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1.
Most commonly referred to someone's age. It is said to be one's "Prime," age, where they look/shine/feel their best. Sixteen is the age where you get multitudes of exciting privileges such as quickie-driviers' license, get a decent job (Host/hostess,) and you're no longer at the very "bottom" of highschool.
Daughter: "Oh, Daddy, please can you get me a convertible when I turn sixteen?"
Daddy: "Of course, Sugar plum!"
Daughter: "Oh, thanks Daddy!"

or,

Wife: "Didn't I just look so good when I was sixteen?"
Husband: "Yeah...This photo book sure has some crazy pictures of us crazy teens!"
by sTelLer_boii August 15, 2008
53 22
 
2.
In hip hop, it refers to a 16 bar verse, which is the average size verse in a rap song. "Bar" is a musical term, sometimes called a "measure", indicating a section with a defined amount of beats in it.
Yo dawg! I'm finna drop these sixteens right about now, get that mic ready!
by KISE1 November 18, 2007
28 5
 
3.
The age when everything you've already been doing becomes legit.
Mum/dad/other "funny adult" - Happy sixteen 'th birthday! you can finally have sex/drink alcohol etc...
you- yeah...finally...
by Pixie101 July 25, 2010
20 9
 
4.
A sixteen is synonymous with a verse. Many rap songs follow the formula of having a sixteen line (8 bar) verse, then choruse, next verse, etc.
you ain't the talk of new york, your sixteens is borin
-game referring to fifty in 300 bars
by devilish November 10, 2005
5 1
 
5.
Plural of Sixteen.
How many sixteens have you got mate?

Loads thanks :-)

Please could you lend me some sixteens?

No, you've got at least 3 thirteens, so no chance sorry!
by Radical Dood May 05, 2010
4 1
 
6.
n. a celebratory shout issued after a successful homosexual orgy
Dap always yells "Sixteen recognize!" whenever he and the gang come back from a successful night.
by cb1000 January 21, 2010
8 14
 
7.
Refers to an album made of around 16 songs.
My G Unit features,
My Eminem sixteens,
My Dr. Dre beats.
-The Game(Runnin)

You ain't the talk of New York your sixteens is boring
-The Game(300 bars)
by Dunk Fest August 04, 2005
7 52