Bar: The Eagle SF....where else can a straight guy feel so welcome in a gay leather bar? Plus they paid us well when my band played there.
Drink: Jack w/Cherry Coke

Cherry Coles RULE!

i have no answer to your question above, but i think the following book is funny:

my favorite bar was this place called the cimmaron in san jose. it was a total dive, but the bartender would be talking to you while pouring your drink, so you'd end up with these monster sized drinks. mmm, favorite drink was a top shelf margarita, on the rocks, no salt. *drool*

Hilltop, Oakland. Tom Collins or gin and tonic.