Cryptic crossword clue
Haunting old boy sings badly, swallowing tablets 9

The most common and most likely answer to this crossword clue is the 9 letter word OBSESSING

I've seen this crossword clue in Financial Times
O
B
S
E
S
S
I
N
G

Buddy explains!

The straight part
We know that "Haunting" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case haunting = obsessing.
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 OBSESSING mean?

OBSESSING verb
  1. (passive, constructed with "with") To be preoccupied with a single topic or emotion.
  2. To dominate the thoughts of someone.
  3. (construed with over) To think or talk obsessively about.

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