"The secret of Caen's success", wrote the editor of a rival publication, was: his outstanding ability to take a wisp of fog, a chance phrase overheard in an elevator, a happy child on a cable car, a deb in a tizzy over a social reversal, a family in distress and give each circumstance the magic touch that makes a reader an understanding eyewitness of the day's happenings.

[6] After high school (where he wrote a column titled "Corridor Gossip") Caen covered sports for The Sacramento Union;[7] in later years he occasionally referred to himself as "the Sacamenna Kid.

[6] His many recurring if irregular features included "Namephreaks"‍—‌people with names (aptronyms) peculiarly appropriate or inappropriate to their vocations or avocations, such as substitute teacher Mr. Fillin, hospital spokesman Pam Talkington, periodontist Dr. Rott, piano teacher Patience Scales, orthopedic specialist Dr. Kneebone, and the Vatican's spokesman on the evils of rock 'n roll, Cardinal Rapsong.

Waiter (and one-time part owner) Edsel Ford Fung, who became famous for berating and insulting the customers, all with tongue in cheek, died Tuesday at age 55, and the skinny old eating place is in mourning.

[18] Now and then an item (usually a joke or pun) was credited to a mysterious "Strange de Jim," whose first contribution ("Since I didn't believe in reincarnation in any of my other lives, why should I have to believe in it in this one?")

On Sundays,[10] current items were set aside in favor of "Mr. San Francisco's" [6] reflections on his unconditional love for his adopted city, musing on (for example): The crowded garages and the empty old buildings above them, the half-filled nightclubs and the overfilled apartment houses, the saloons and the skies and the families huddled in the basements, the Third Street panhandlers begging for handouts in front of pawn shops filled with treasured trinkets, the great bridges and the rattle-trap street cars, the traffic that keeps moving although it has no place to go, thousands of newcomers glorying in the sights and sounds of a city they suddenly decided to love instead of leave."

[23]An occasional column was given over to serious matters, such as a May 1, 1960, piece on the upcoming execution of Caryl Chessman, which included Caen's recollection of witnessing a hanging as a young reporter: Suddenly the door behind the scaffold swung open and the nightmare scene was enacted in a flash.

[12]: 94 On December 12, 1960, Caen wrote: While you're making out your Christmas cards, you might remember to send one to Francis Gary Powers, c/o American Embassy, Moscow, USSR.

In April 1996 Caen received a special Pulitzer Prize (which he called his Pullet Surprise) for "extraordinary and continuing contribution as a voice and conscience of his city.

After a motorcade and parade ending at the Ferry Building, Caen was honored by "a pantheon of the city's movers, shakers, celebrities and historical figures" including television news legend Walter Cronkite.

Noting that several San Francisco mayors (sitting or retired) were at liberty to attend, Caen quipped, "Obviously, the Grand Jury hasn't been doing its job."

[6] His funeral‍—‌held at Grace Cathedral despite his Jewish heritage[39] ("the damndest saddest, most wonderful funeral anyone ever had, but the only man who could properly describe it isn't here," said close friend and local nightclub owner Enrico Banducci)[12]: 20 ‍—‌ was followed by a candlelight procession[40] to Aquatic Park, where his will had provided for a fireworks display—climaxed by a pyrotechnic image of the manual typewriter he had long called his "Loyal Royal".

"No other newspaper columnist ever has been so long synonymous with a specific place ... Part of his appeal seemed to lie in the endless bonhomie he projected," said his New York Times obituary, comparing him to Walter Winchell "but with the malice shorn off."