I lived in San Francisco for a couple of years in the early days of the dot-com boom, back when rents were merely outrageous, unlike today with the billionaires pricing out the millionaires. For the most part, I enjoyed my adventure out there. Having only lived in the midwest up to that point in my life, I felt it gave me a little perspective on this enormous country of ours. But here’s the thing: it was cold, Jack. Colderna well-digger’s ass. So it was important to go drinking in San Francisco on occasion.

Everyone brings up Twain’s quote about the coldest winter he ever knew was summer in San Francisco, and that’s a funny bit of hyperbole, but San Francisco, while never, ever as cold as the coldest days in the midwest, nonetheless made me feel chilled to the soul-bone in a way I never knew in Michigan or even Chicago. This happened for three reasons: 1) it was chilly and damp much of the time, 2) I lived in an old house with poor insulation and a crappy “heating system” (essentially a lame space heater mounted on the wall in a hallway with 15-foot ceilings), and 3) SF never really warmed up like it did in a midwest summer where the really warm weeks baked the previous winter’s chill completely out of your body, until in a perverse state of nostalgia you actually longed for January.

So, yes, San Francisco was a truly goddam chilly city, but the upside was that indoor activities were enjoyable year-round. You didn’t often feel you were missing out if you stayed inside, went to the movies, or read in your bedroom all afternoon. Another equally chilly day was right around the corner. And around the corner after that, too.

One of the bonuses of living in a climate like that is every day is perfect for popping into a warm, cozy place for a drink and some downtime. From the first time I visited San Francisco, and friends took me to a woody pub near the Presidio called Liverpool Lil’s after a cold bike ride over the Big Red Bridge, I discovered a bunch of great bars, taverns, coffee shops and dives that made months of chilly, foggy days that much more tolerable. I could name 20 (and do, below), and I’ve commemorated three so far as artwork: Caffé Trieste, Trad’r Sam, and Café Vesuvio. These are the first Great Good Places I’ve done for San Francisco, a great good city if ever there was one.

Drinking in San Francisco, Coffee Dept:

Trieste was the first coffee house I ever hit in SF, and I hit it hard. I was visiting then — not living there yet — and I read in a guidebook that a quadruple shot of espresso at Caffé Trieste was one of the best legal highs in the world. I went for it, read and drew for hours, tried to bring it down a notch with some wine, shared a table with three local characters who didn’t mind my eavesdropping, walked across half the city, and stayed wide awake until about 4:30 a.m. It was worth it, and Trieste became a go-to of mine when I lived there. My favorite thing to order was (and still is) the Caffé Wien mit Schlag, German for “pitch-black coffee with a giant glob of whipped milkfat on top.” Delicious. Equally delicious is the vibe of the place. The history. The beats hung out there. So did Francis Ford Coppola, and he wrote the screenplay to The Godfather there. First cappuccinos in San Francisco? You got it. Trieste.

Drinking in San Francisco, Funky Style:

I love that place. And about two blocks away there’s another place I love: Café Vesuvio. It’s a grand old pub sitting on a Columbus Avenue corner across an alley from the fabled City Lights bookstore. A real beauty, almost operatic in its dramatic but absolutely pubby grandeur. It’s another old beatnik hangout with lots of Kerouac & Co. memorabilia on the walls. There are plenty of window seats for reading, cool bartenders, and a balcony. I love a place with a balcony; it gives you another perch with a different perspective of the interior and the streets outside. And balcony has soul, as George Carlin once said.

Drinking in San Francisco, Retro Tiki Dive:

The third place I drew is a weird one: Trad’r Sam, the oldest extant tiki bar in Frisco. (Oh yes, you can say “Frisco,” but only in conjunction with locally-based tiki bars, gumshoes, dockworkers, and no-good two-timing dames.) Anyway, Sam’s opened up shortly after Trader Vic’s, and there’s some dispute as to who copied whom, name-wise, but the bottom line is this: Trad’r Sam has one bitchin’ mother-grabbing sign. It’s the size of Delaware and it’s attached to a two story hut. It’s neon. It’s lightbulbs. It’s green and yellow. It’s awesome. And that’s why it gets the Great Good Places treatment. Inside it’s a solid dive, all shabby rattan, lethal drinks and throwback horseshoe bar, but the sign… the sign is — ‘ow you say? — a real humdinger.

Drinking in San Francisco, Bonus List:

Tennessee Williams, in all his mustachey bitchiness, once said “America has only three cities: New York, San Francisco, and New Orleans. Everywhere else is Cleveland.” When in SF you could do worse than than visit these places on an inevitably cold, damp afternoon. There for a week? Here are 20 more suggestions for hanging out and drinking in San Francisco:

• Tommy’s Joynt
• The Saloon
• Club DeLuxe
• The Kezar Pub
• The Riptide [It burned down, dammit, but will be back]
• The 500 Club
• The Owl Tree
• Gino and Carlo
• The Pig and Whistle
• The Irish Bank
• Zeitgeist
• Trick Dog
• Toronado
• Liverpool Lil’s
• Yancy’s Saloon
• Nite Cap
• Smuggler’s Cove
• The Phoenix
• Suppenkuche
• Spec’s Twelve Adler Museum Cafe

Oh, and how about Mr. Bing’s just for good measure?