via The Bold Italic.

SAN FRANCISCO IS A LOT OF THINGS.

It’s hippies, hipsters, vagrants, flagrants, artsy, fartsy, and more. You name it, and it probably lives here. And accordingly, no single nickname has ever really stuck for Saint Frank.

Riffs on the grand title of our city come and go. Many of them are “locals only” tags. But no major urban destination can escape the nicknaming process – just look at the Big Apple or the Windy City. Like most things San Francisco, there’s no consensus on which nickname – if any – is appropriate. We’ll leave that question for the comments section. In the meantime, here’s what I’ve discovered about the history of San Francisco nicknames.

THE GREAT DEBATE: FRISCO

The St. Louis–San Francisco Railway known as the “Frisco” began
operating in 1876, but the nickname is as old as the American West.
Herb Caen, the Pulitzer-winning San Francisco Chronicle columnist,
was adamant that no one call his fair city by such a sliced up moniker.
Instead, “Caress each Spanish syllable, salute our Italian saint.
Don’t say Frisco and don’t say San-Fran-Cis-Co,” he advised.
“That’s the way Easterners, like Larry King pronounce it. It’s more
like SanfrnSISco.” Yet, cultural forces from Otis Redding (“headed
for the Frisco bay”) to Pink Floyd (the unofficial Darkness Over Frisco
live album) to Google (search “Frisco” and see what comes to the
top of the page) keep the name associated with San Francisco.

Here’s the thing with “Frisco”: Nicknames are supposed to embody
some overall characteristic, not just act as a lazy surgery of the
city’s name. There’s a reason we don’t call New York “Nork” when
we’re feeling saucy. It’s the “The City That Never Sleeps” for poetic
reasons. Just because “Frisco” sounds like a place (and it is,
in Texas and Colorado), doesn’t make it a good nickname. No one
would get on the I-5 and head south for “Agles.”

(Pro tip: If an out-of-town friend calls it Frisco, avoid the soapbox.
San Franciscans have a rep for being uptight jerks about the nickname.
Don’t play into the stereotype. They’ll eventually notice you never
call it that anyway.)

THE EXPLAIN-Y ONE: BAGHDAD BY THE BAY

Such a name may trigger worries of negative geopolitical undertones,
but this was actually the title of a collection of Caen essays about San
Francisco (and a persistent nickname he used). The reference to the
ancient Iraqi capital – which is also near Babylon – was meant as an
indication of the wide range of characters and cultures you found in
San Francisco decades ago. This past decade has put our relationship
with Baghdad in a tough place, though. Anyone hearing the phrase for
the first time needs a delicate explanation. That’s not the sign of a
great nickname. Sorry, Herb.

THE MAYBE A CENTURY AGO ONE:
PARIS OF THE WEST

This was a common nickname at the turn of the twentieth century
used to coax tourists and lure Easterners to move to our glorious
city on the other side of the railroads. But no proud urban destination
likes to be thought of as the “something else” to a better-known city,
so it’s fallen out of use.

THE LOCALS-ONLY ONE: THE CITY

The City is a local’s nickname not because of any exclusivity,
but because if you are within a reasonable distance of another
city, people will have no idea what you’re talking about. The
capital letters don’t translate in conversation.

But when used appropriately, the nickname creates a nice recall
of the days of Old West yore, when San Francisco was the only
metropolitan area within conceivable traveling distance. If you
told someone in the Salinas Valley that “I’m heading to The City,”
they’d know what you meant. Oakland and San Jose were still
glimmers in the eyes of today’s giants. Everything between here
and LA was wild ranching and farmlands. “The City” didn’t need
capital letters.

THE BEST ONE (SO FAR): CITY BY THE BAY

Keep it simple. You can drive over the bridges a thousand
times and still catch yourself lost in the majesty of San Francisco
nestled against the water, islands, sailboats, and sunshine of
the bay. Let’s call a spade a spade.