This subject came up when I was reading
alt.usage.english many years ago.
The original thread was spawned by the
juvenile riddle to which the correct answer is:
Smiles
Why? Because there's a
mile between the first and last letters.
A prompt response from one poster was that
Beleaguered must therefore be a longer word
since a
league is three
miles.
That was when the thread took off:
"That doesn't count because it requires you to add
too many letters."
"
laud is longer, because the
AU it contains is an
astronomical unit!"
"In that case
glyph contains a
light year!"
"
Abbreviations don't count!"
"She spelt
Beleagered wrong!"
and so on and so forth.