Musician, college president and Woodside resident Bob Stiff


Woodside resident Dwight Robert "Bob" Stiff, a self-taught professional musician, twice president of Canada College, and the husband of former Woodside mayor Joan Stiff, died peacefully at home on March 15. He was 88.

Mr. Stiff was a native of Detroit, where he developed a love of music, literature and baseball. He taught himself to play the alto saxophone and the clarinet, largely by listening to big-band records. He told his family that he graduated from high school on a Friday and by Monday, he was on the road with a big band.

In the band, he found himself in "a truly excellent" sax section and "learned to listen" to the brass and the rhythm sections, according to his family's account. "(I) learned that when all the sections of an individually talented band are doing that kind of listening, the result can be musically thrilling."

In the Bay Area, Mr. Stiff played with the Walt Tolleson Big Band, appearing at venues such as the San Francisco Symphony's Black and White Ball, the Saint Francis Yacht Club and the Olympic Club.

He had a bachelor's degree in English from the University of Redlands and a master's degree in English and a minor in music from San Francisco State College. He taught at Hillsdale and Mills high schools and at the College of San Mateo and at Canada College, where he was the language arts chairman.

He served as president of Canada College from 1974 to 1975 and from 1983 to 1990. Between terms, he worked in the college district office as a program coordinator. He would cite his experiences at the community colleges as some of his best.

Bob and Joan Stiff were married for 50 years and raised four children in Woodside. He will be remembered, his family said, for his warmth and generosity, his views on literature, music, politics, movies and sports (he was a "huge" Giants fan), and his intelligence and sense of humor. "He had a great life and we were so lucky to have him in ours," his family said.

Mr. Stiff is survived by daughters Deidre of San Jose and Laura of Santa Cruz County; sons Paul of Mill Valley and Eric of Sacramento; five grandchildren and two great-grandchildren. Joan Stiff died in 2005.

In lieu of flowers, the family asks that donations be made to the Robert Stiff Scholarship Fund, which assists academically meritorious students planning to major in English or literature but in need of financial aid.

Go to or send a check to the SMCCC Foundation, 3401 College of San Mateo Drive, San Mateo CA 94402. Please include "Robert Stiff Scholarship" in the comments section or online on the check.

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Like this comment
Posted by Jim Semitekol
a resident of Woodside: other
on May 27, 2015 at 6:36 pm

I only met Bob late in life and had the pelaseure of knowing him for the past 3 or 4 years. An unbelievable gentlemen who welcomed everyone he met. An unsurpassed musician who had one of the sweetest tones on saxaphone or clarinet I ever heard. Even though I only knew Bob a short time I will miss his personality and music.

Like this comment
Posted by Steve Dambrosio
a resident of another community
on May 27, 2015 at 7:14 pm

I had the great pleasure, for several years, of sitting right next to Bob in a jazz band. He was always friendly and kind. He not only taught me the art of musicianship but set a sterling example on how to be a positive force in every situation. I feel fortunate to have been within the influence of his halo. We miss you Bob.

Like this comment
Posted by Mike Kelly
a resident of another community
on Aug 13, 2015 at 11:03 am

Bob was my friend, a mentor, and one of the finest gentlemen I have known. I miss him greatly. The influence and wisdom he imparted to his musician friends is a lasting gift to us all.

Mike Kelly

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