Toby C Hess

Toby C Hess

September 17, 1936 - December 14, 2025

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Obituary

MADISON - Toby Charles Hess, age 89, of Madison, passed away on Sunday, December 14, 2025, at William S. Middleton Memorial Veterans Hospital. He was born on September 17, 1936, in Madison, Wis., the son of Tony and Gladys (Starks) Hess.


Toby’s family owned the Hess Cooperage on Winnebago Street in Madison, where he proudly worked alongside his father, aunt, uncles, and grandfather. Some of the barrels crafted there still remain on display at the National Beer Museum in Potosi, Wis.-a lasting testament to his family’s craftsmanship.


Toby served his country in the U.S. Army as a military police officer before marrying his former spouse, Glenna. Together they raised four children.


Professionally, Toby dedicated many years to the hardware industry, working as a sales representative throughout southern Wisconsin. Later in his career, he purchased a hardware store in Slinger, Wis., and eventually transitioned into retail, working at Kmart and Walmart until his retirement.

In retirement, Toby found joy in fishing and tending to his garden. He cherished a special friendship with Linda Gullickson and delighted in spending time with her grandchildren. Toby especially loved gathering around the table to play cards-euchre being his favorite game.


Toby is survived by his sons, Randall Hess and Timothy (Julie) Hess; daughters, Leila Hess and Darla Jankoski; grandchildren, Anthony, Amber, Toby, Jasmine, Marissa, Travis, Christine, Karen, Kelly, Tommy, Claire and Courtney; 22 great-grandchildren; and special nephew, Curt Morey. He was preceded in death by his parents; sister, Jackie Morey; and brother, James Hess.


A celebration of life will be held at SUNDOWN SALOON, 57 S. Stoughton Road, Madison, from 1 p.m. until 4 p.m. on Saturday, January 31, 2026. A private family burial will take place at Roselawn Memorial Park.
 

Memorials may be made to Warrior Rising, which empowers veterans by providing opportunities in business education, coaching and professional development. Online condolences may be made at www.gundersonfh.com.


Gunderson East
Funeral & Cremation Care
5203 Monona Drive
(608) 221-5420


Events

31
Celebration of Life
Sat Jan 31, 2026 @ 1:00 PM - 4:00 PM CDT
Sundown Saloon • 57 S. Stoughton Road, Madison, WI 53714
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Toby
AH
A Memorial Tree was planted for Toby Charles Hess
Other •
We are deeply sorry for your loss ~ Gunderson Funeral Home - Madison
PK
Patty Kraiss
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Always the charmer Toby! I will miss you
DS
Doreen Smith
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I remember talking to Toby onthe phone and him telling me about being a sharp shooter in the service. They thought he shot through the the target only once till they took it up stairs and looked again and found out he had shot through the same whole three times. He said he guarded the President at one time in his service to our country.
RS
Ron Scalissi
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Toby was a great guy, one of the nicest people I ever met. I worked on his vehicles for years. He would stop by on his daily walk just to shoot the breeze. Sorry for your loss. Ron Scalissi (Ron's Service Center)
DW
David Wolter
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I remember working with Toby at Walmart and some of the good times we had joking around before the store opened and after it did especially the one weird operator we had. He new his hardware and great cust service. Was a great person to work with.
LH
Leila Hess
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