10
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Plain Diamonds
Doobie Fair Lady
Host Mallet
Mr Mallard
Sprint Defense Escher
Large Not Large
Binary Shackles
Infantry Man Child
Miss Nervous
Half Byte

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  • $\begingroup$ Does the trivia tag apply here? I imagine that the answers will be dependent on your geography; not all candy bar brands are available in all parts of the world. $\endgroup$ – Ian MacDonald May 11 '17 at 17:41
  • $\begingroup$ In fact, the brand of candy bar that they hang out with is of no consequence and the reference to candy bars serves merely to stimulate a hint as to what kind of people these may be. $\endgroup$ – Forklift May 11 '17 at 17:43
10
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Partial answer:

Each phrase clues a different hip hop artist. A line of poetry in hip hop is called a bar, and you might call a particularly sweet line a candy bar. (OP revealed in comments that candy bar was supposed to clue rapper, from wrapper).

Plain Diamonds

VANILLA ICE (due to Personman), although JUST-ICE (suggested by M Oehm) also fits.

Doobie Fair Lady

JAY Z (J + Nissan Fairlady Z—revealed by OP)

Host Mallet

MC HAMMER

Mr Mallard

DRAKE (a male bird—revealed by OP) (My original guess was BIRDMAN.)

Sprint Defense Escher

RUN-D.M.C. (RUN + D + M.C.)

Large Not Large

BIGGIE SMALLS

Binary Shackles

2 CHAINZ

Infantry Man Child

SOULJA BOY

Miss Nervous

Possibly NELLY (suggested by Duncan), from the expression nervous Nellie. This clue seems more indirect than the others, and I am not sure the function of miss.

Half Byte

50 CENT (This clue plays on the ambiguity of bit. A bit is 12.5 cents as well as a unit of data in computing, eight of which constitute a byte—confirmed by OP.)

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  • 1
    $\begingroup$ Plain Diamonds is Just Ice. $\endgroup$ – M Oehm May 11 '17 at 18:27
  • 2
    $\begingroup$ Vanilla Ice, presumably. $\endgroup$ – Personman May 11 '17 at 18:31
  • 1
    $\begingroup$ Miss Nervous = Nelly (Nervous Nellie) $\endgroup$ – Duncan May 11 '17 at 18:33
  • 3
    $\begingroup$ It seems we've been informed that the "with candy bars" clue is actually about the "wrapper" pun, not the more complex explanation given in this answer :) $\endgroup$ – Personman May 11 '17 at 18:37
  • 1
    $\begingroup$ I refused to correct it because it sounded way cooler than my lame pun. $\endgroup$ – Forklift May 11 '17 at 18:38

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