1. What do the following clues have in common?

College officer
Put on clothing
Swindler's target
British nobleman
Successful rival

2. What do the following phrases have in common?

BLACK SHEEP
SHOW STOPPER
FIELD GOAL
POINT GUARD
PUNCH LINE

HINT:
2. Two new words can be inserted into each phrase

Answers:

1. Each clue can be answered with a word that is also a man's name:

College officer - Dean
Put on clothing - Don
Swindler's target - Mark (Patsy)
British nobleman - Earl
Successful rival - Victor 

2. Between the two words of each phrase, two additional words can be inserted - in the form of AND _____.  The first three words of the new phrase form a familiar expression.

BLACK AND BLUE SHEEP
SHOW AND TELL STOPPER
FIELD AND STREAM GOAL
POINT AND CLICK GUARD
PUNCH AND JUDY LINE

Credits
#1:
LA Times Crossword
January 27, 2008
Josiah Breward
PEOPLE PERSONS

#2:
LA Times Crossword
December 27, 2009 
Barry Silk and Doug Peterson
AND ANOTHER THING