Cryptic crossword clue
With dry wit, his life’s said to be carefree 5

The most common and most likely answer to this crossword clue is the 5 letter word WRYLY

I've seen this crossword clue in The Guardian
W
R
Y
L
Y

Buddy explains!

The straight part
We know that "With dry wit" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case with dry wit = wryly.
The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does WRYLY mean?

WRYLY adverb
  1. In a wry manner.

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