Bob came early to the job of making people laugh and stayed at it late. He was a lifelong freelance writer, which is sometimes a euphemism for being frequently unemployed.
Not in Bob’s case.
He was a successful freelance writer, always working, contributing to dozens of national and regional magazines, including high-profile work in the 1970s for Playboy, for which he produced the annual “Celebrity Christmas Carols” parodies.

For several years he wrote a health advice column under the name “Dr. Oui” for Oui magazine when Hugh Hefner owned it. He also wrote for Penthouse.
He wrote about baseball, specifically the “Swinging A’s” in the ’70s. He is credited with coining one of the most timeless quotes concerning baseball’s love of numbers:
Baseball fans are junkies, and their heroin is the statistic.
This century he was a successful internet “content provider,” maintaining a blog he called “Humor Me II,” the successor to “Humor Me.”
Over the years, he placed items in the columns of Herb Caen and Leah Garchik’s “Overheard in the Bay Area.” Without that distinction, strike your name from the Bay Area List of Laughter.

He wrote op-ed pieces for the Chronicle and pieces on the local comedy scene for the pink section. 

He wrote letters to the editor, some of them surprisingly public spirited, once chastising San Francisco school board members for removing the names of U.S. presidents from local schools but suggesting, seriously, that schools be named after those “who drew the country’s attention to San Francisco in a positive fashion,” like Jerry Garcia, Janis Joplin, Willie Mays, Rev. Cecil Williams and Joe Montana.
This was not his prevailing mood as a writer. He was not Garrison Keillor. He was not cozy. Commenters on his work sometimes described the objects of his wit as “skewered.”Some of his friends called him a curmudgeon, though a lovable one.

Is this a curmudgeon? He and wife, Gloria, mentored a couple local kids from grade school through high school.
“The kids really took to Bob,” Gloria says. “He was a great math tutor for homework. But they found him to be very funny, which was no surprise. He would pick stupid movies at the video store with them and watch whatever they wanted. He told jokes, made faces and goofy sounds. Bob truly enjoyed making others — and himself — laugh.”
One thing about funny men. Most of them can’t stop being funny, which means for every joke they sell, there’s two more they give away, particularly in casual conversation, where Bob shone.
With his longtime friends, Bob was an on-again, off-again member of a fantasy baseball league. His running commentary turned the annual gathering into a comedy roast. “When it came to making people laugh,” says journalist and fantasy league member Kevin Berger, “Bob had the gift. He was The Natural.”