The most common and most likely answer to this crossword clue is the 4 plus 5 letter word HIGH TIMES
I've seen this crossword clue in Independent
H
I
G
H
T
I
M
E
S
Buddy explains!
The straight part
We know that "Might he and I tipsily start to sing, having these" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case might he and i tipsily start to sing, having these = high times.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.