22 across
Son
sent
to
prison,
one
ultimately
angry-looking,
expressed
a
little
amusement
(9)
Son sent to prison, one ultimately angry-looking, expressed a little amusement (9)
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The definition is at the end of the clue.
How the clue works
Look at expressed a little amusement at the end — that's your definition, as in sniggered or laughed quietly. For the wordplay, S is the abbreviation for son, NICK is slang for prison, E is the last letter (that's the "ultimately") of one, and RED means angry-looking — string them all together and there's your answer.