Robert Earl “Bob” Olsen Jr., 85, died on Monday, July 27, 2026, after a brave struggle with heart disease and Parkinson’s. His heart gave out as he was surrounded by his family at his home in Madison.
Bob is survived by his wife of 59 years, Carol; daughter, Laura Olsen Dugan; son-in-law, Darin Dugan; daughter, Julia Peterson (Ted); grandchildren, T.J. (Hannah), Emma, and Casey Peterson, and Conner and Katherine Dugan; and great-granddaughter, Audrey Peterson. He is also survived by his sister, Sharon Olsen Abrams. He was preceded in death by his parents, Robert Earl Olsen Sr. and Julia Arnold Olsen; and his beloved niece, Zara Ariel Abrams.
Bob was born on Aug. 15, 1940, in Brooklyn, New York. Within a year, his parents returned to the Chicago area. Bob’s father was soon serving in the military in World War II. Bob’s mother moved to Sharon, and the family lived with her aunts on the family farm, which had been settled by Norwegian immigrants. After the war, the family moved permanently to Sharon.
Bob attended the University of Wisconsin-Madison, majoring in sociology, and received his J.D. in 1969. He was employed by Foley and Capwell in Racine from 1969 to 1971. Then, Bob became an Assistant City Attorney for the City of Madison until he retired in 2009. Bob’s career was centered on public service representing the City of Madison.
Bob had many hobbies, and enjoyed becoming an expert in them. The most important hobby was traditional jazz music. Bob acquired all forms of records, and recorded many bands and produced tapes that were good enough to be issued professionally. Every year, he attended two jazz festivals that featured the music of Bix Beiderbecke. He also enjoyed twentieth-century literature, photography, and fishing for trout in streams west of Madison. Bob spent several years researching his great-uncle as one of the models for the Coca-Cola Santa Claus, as painted by Haddon Sunblom. This led Bob to study illustration and pin-up art. Bob published an article in Illustration Magazine in 2006. In retirement, he learned to play the ukelele. He acquired numerous ukeleles and ukelele music, which joined his collection of cornets and trumpets.
Bob was known for his humor and wit. He continued to say short funny comments, even as he said less and less. He loved playing small jokes on his wife, daughters, and grandchildren. His daughters and grandchildren have fond memories of harvesting candied fruits from the “candy plants,” large sunflowers with candy balanced on the leaves. He also enjoyed flying kites with his grandchildren and playing Old Maid while sitting in his beloved gazebo with his grandchildren.
A memorial service will be held at Gunderson Fitchburg Funeral and Cremation Care, 2950 Chapel Valley Road, Fitchburg, at 4:30 p.m. on Monday, Sept. 14, 2026. A visitation will be held at the funeral home from 2:30 p.m. until the time of the service on Monday. A celebration of life gathering will follow the service at The Fairway Lounge, 2949 Triverton Pike Drive, Fitchburg, from 5:30 until 8 p.m.
The family extends gratitude to the health care professionals at SSM Health Dean and Agrace Hospice Care, whose exceptional care and compassion gave comfort and dignity to Bob.
Bob led a full life. One of his favorite books was The Great Gatsby by F. Scott Fitzgerald. “So we beat on, boats against the current, borne back ceaselessly into the past.”
Online condolences may be made at www.gundersonfh.com.