For burley-heavy blends, I prefer black coffee or Guinness, depending on the time of day. For blends with any noticeable amount of Lat, I prefer Guinness hands-down. I too enjoyed the Pogues reference; loved those guys. FWIW, the quote has often been attributed to Winston Churchill, but some sources say that's a load of bunk.
I love sweet iced tea with just about anything. It's a great match for VAs and VaPers.
I really like coffee with fuller Balkans and heavy hitting Burley-heavy blends. Espresso and HH Old Dark Fired, Solani 656 or GH&Co's Dark Flake is fantastic.
I quit drinking alcohol before I started smoking a pipe, so I got nothing in that front.
Black Coffee ... whatever's handy (I'm not picky about coffee as long as it's not too weak) works well with most of my baccy.
Any top shelf bourbon. It goes well with nice stout blends
Mountain Dew. It's really sweet and citrusy so it compliments many blends really well.
The only thing that improves a bowl of good tobacco and a cup of black coffee is more tobacco & coffee.
-maybe a bite or two of bacon
Coffee is my favorite, hot or iced tea is also good. I also usually have a glass of water handy.
I don't drink any more, but for all you beer drinkers out there who find the gas a little much with a pipe, try Guiness draught, I used to really enjoy this flavorful and very lightly carbonated beer with a pipe.
Condor Long Cut in a large bowl complimented with a glass of Shepherd Neame's India Pale Ale goes down a treat for me.
Even better when there is snooker* on the telly ::
*Snooker is a game perhaps not understood by American members as it doesn't involve wearing a crash helmet and full body armour :nana:
I often find that I like a sweet drink to balance out a savory/strong/stout tobacco, or vice versa.
-So some ruby port with something beefy like Nightcap or a cigar. (Generally, ruby port is far too sweet for me to drink alone, but this seems to work.)
-Coffee with a mild aromatic like Russ's Cinnamon Roll.
-Or a middle of the road pairing--Frog Morton's Cellar with some scotch.
But 95% of the time I just enjoy the tobacco by itself.