Professional comedian Simone Alexander was leading us through the streets of San Francisco on a walking tour that was less a tour and more a movable game show. Actually, it was more a parody of a game show. Simone was the emcee and we were the contestants.

Those who answered correctly were given chocolate coins. Those responding incorrectly were rewarded with misfortune cookies, gag fortune cookies that Simone said are "stale on the outside, bitter on the inside."

We stood in front of the majestic Fairmont Hotel. Simone asked, "The members of what international peace organization were housed here in 1945: A) the League of Nations B) the United Nations C) the International Legion of Doom and Gloom D) OPEC?"

"The League of Nations," a group member responded.

Wrong. The correct answer is the United Nations. The misinformed tourist selected a misfortune cookie and found that the bitterness of the inside described the fortune rather than the taste. It read, "If you have nothing nice to say to someone, consider throwing something instead."

Further on, in front of the St. Francis Hotel, we were asked, "Who tried to assassinate President Gerald Ford on this spot in 1975: A) Squeaky Fromme B) Sara Jane Moore C) Sara Jane Olson D) Charlton Heston?" The answer is Sara Jane Moore, and the bullet hole is still in the doorway. An erroneous answerer picked a misfortune cookie with a message reading, "Something extremely vague will happen to you soon, or perhaps later."

Well, it beats "You will soon find yourself with 2 crying children, which distracts you from finishing the ransom note," which I was misfortunate to receive later on.

Simone was one of a handful of comics who moonlight — or to be more accurate, sunlight — as guides for FOOT! Fun Walking Tours, known casually as FOOT! (but not Foottours, a different Bay Area company), in which the standard city walking tour is injected with a dose of offbeat humor. After all, this ain’t Tulsa. Your guide will be a comedian but will not be Simone, who has since left FOOT! to further pursue her comedy career.

FOOT! offers 11 tours on topics from the sublime to the subculture, from gold diggers literally to gold diggers figuratively. The genesis of FOOT! was in 1999 with comedian Robert Mac’s stand-up act in a Fisherman’s Wharf area comedy club. Mac recalls, "About 80 percent of the crowd was from out of town, and they had a lot of questions about San Francisco, so my act became a kind of question-and-answer act. Being a transplant from Arizona, I was learning a lot about the city, and I put some of that material into my act, discussing the quirky things about the city."

Next, a friend heading to town for a convention asked whether Mac could lead a city tour for his group. Mac took that one step further in 2000 by hiring working professional comedians to give additional tours. Today there are 10 comedians on staff.

We took the company’s flagship tour, called "The Whole Shebang," a three-hour jaunt through Nob Hill, North Beach and Chinatown. It is not unusual for a guide to ad-lib during the monologue. As Simone discussed the six fires that hit the city from 1849 to 1851, she spotted a portly pedestrian with a white beard. "Oh, and there is Santa Claus," she said before continuing to explain that San Francisco’s repeated fires and recoveries are the reason the city’s official flag bears an image of a phoenix rising from the ashes.

Despite the wisecracks, we actually did learn a lot about the city. Standing in Union Square, the city’s biggest hotel district, named for the 19th-century pro-union rallies frequently held there, Simone pointed to the towering Dewey Monument. In 1905 it was dedicated to both Adm. George Dewey and the recently assassinated President William Mc­Kin­ley. But the real story is the figure atop it.

To the casual visitor’s eye, she is an anonymous but stately bronze female figure with a wreath in one hand and a trident in the other. In reality she was one of San Francisco’s greatest benefactors. Her name was Alma de Brette­ville (1881-1968), which might sound as though she was reared in the high society enclave of Nob Hill, or Snob Hill as some call it, but was actually from a dirt-poor farming family from the city’s Sunset District. A 6-foot-tall beauty, she found she could make good money by posing for artists. It was Dewey Monument sculptor Robert Aitken who transformed the statuesque Alma into the statue gracing Union Square.

Oh, Alma had one other goal: marry rich. She accomplished that feat at age 24 by marrying millionaire sugar magnate Adolph Spreck­els (son of the founder of Spreckels Sugar Mill on Maui), who was well into his 50s. This, we were told, "officially made him the first sugar daddy." (Groan!) But Alma used her riches for good, funding the city’s Palace of the Legion of Honor, home of the largest collection of Auguste Rodin sculptures, and providing relief during both world wars and the 1906 earthquake.

No San Francisco historic tour can be complete without a discussion of the catastrophic 1906 quake, and Simone was ready with a barrage of facts and laughs. "Eight-point-three on the Richter scale, and they felt it all the way to Vancouver, where it was 11.3 on the Canadian Richter. It is said that people in Oakland could read at night by the light of the fires caused by the earthquake, which is an amazing fact because nobody in Oakland reads at night."

But the truth is that in its time the earthquake was no laughing matter. A total of 250,000 people, or about 60 percent of the city’s 400,000 residents, were displaced, and some of the more pious residents of the city said it was God’s vengeance on the local population for their sinful ways. There was no class distinction among victims. The mansions of railroad barons Mark Hopkins and Leland Stanford were burned, and while the exterior shell of the Fairmont Hotel was saved, its glorious interior was ravaged.

The other requisite history topic here is the Gold Rush. During the rush’s heyday in the summer of 1849, the city’s population doubled roughly every 10 days. But what many don’t know is that 10 years later California was the site of a silver rush, and the city’s bartenders did their best to loosen the lips of miners who stopped by to enjoy liquid refreshment. While in the Nob Hill section of town, we stood by a gate that is called one of the finest examples of Victorian metalwork and which once surrounded the home of silver baron James Flood. Flood paid a man $30,000 a year — in 1860s dollars — to polish it. Oh, and those nosy bartenders? After they learned where the silver was, they went from serving champagne to bathing in it.

The Whole Shebang tour is not entirely outdoors. We entered the Huntington Hotel and walked into the Big Four Bar, named in honor of the four main backers of the first transcontinental railroad: Hopkins, Stanford, Collis P. Huntington and Charles Crocker (whose Nob Hill mansion home is now the site of Grace Cathedral, the third-largest Episcopal church in the United States). Hanging on a wall is a panoramic photograph of San Francisco at age 30 in 1879, when downtown was filled to the brim with housing but Nob Hill’s residences were just being built.

The Chinatown portion of the tour usually makes a visit inside a fortune cookie factory. We were short on time, so we skipped the factory in favor of an abridged narration. We learned those colors on the balconies of Chinatown have symbolic meanings: Red stands for happiness, gold for wealth and green for abundance. Chinatown’s triple-decker homes are fairly uniform in style; shops are on the bottom floor, residences in the middle, and some have temples on the top.

It is by the fortune cookie factory that we were given traditional fortune cookies with messages such as "You have sound business sense."

Sorry, but the misfortune cookies were a lot more fun.

Michael Schuman is an award-winning travel writer and author who is based in New Hampshire.