That’s such a pretty song but it makes no sense to me, except I know that it’s a Yale thing.
I love it too. It is pretty. My father used to sing it to me and he did explain it when I was a kid but the explanation being so known to him then is a vague memory for me now. Here is the explanation on the net:
“The Whiffenpoof Song
To the tables down at Mory’s, to the place where Louis dwells
to the dear old Temple Bar we love so well
sing the Whiffenpoofs assembled, with their glasses raised on high
and the magic of their singing casts its spell
The origins of The Whiffenpoof Song can be traced to a 1907 winter trip by the Yale Glee Club, when two of the group’s founding members created a humorous adaptation of the Rudyard Kipling poem, “Gentleman Rankers.” Upon the conclusion of the song’s premiere at Mory’s Temple Bar, the singers declared it their anthem, “to be sung at every meeting, reverently standing.”
I remember my father did say they knew the owner of the bar and it was a kind of dear gathering place for the boys at Yale.
Here is Kipling’s poem (part of like the song) (which I did not know of till now):
To the legion of the lost ones, to the cohort of the damned,
To my brethren in their sorrow overseas,
Sings a gentleman of England cleanly bred, machinely crammed,
And a trooper of the Empress, if you please.
Yea, a trooper of the forces who has run his own six horses,
And faith he went the pace and went it blind,
And the world was more than kin while he held the ready tin,
But to-day the Sergeant’s something less than kind.
We’re poor little lambs who’ve lost our way,
Baa! Baa! Baa!
We’re little black sheep who’ve gone astray,
Baa—aa—aa!
Gentlemen-rankers out on the spree,
Damned from here to Eternity,
God ha’ mercy on such as we,
Baa! Yah! Bah!
https://www.whiffenpoofs.com/history
and here is my favorite recording by Bing Crosby, with the Glee Club, and is very sentimental. I am still astonished at how good he was, though it was now a long time back.
https://www.youtube.com/watch?v=NZSdvp7OxCM