MIDDLETON - Charles “Chuck” Bollenbach, 79, of Middleton, Wis., passed away peacefully on October 8, 2025, after a long battle with cancer. He left behind a lifetime of stories, laughter, and a trail of ski tracks through the snow.

Chuck was a wild spirit who believed life was meant to be lived loud, laughed at often, and especially, toasted to with good friends. He loved his family and never missed a chance to make a memory, tell a tall tale, or turn an ordinary moment into something worth talking about for years to come.

He was born in Madison, Wis., on May 8, 1946, in the back seat of a car (according to him) - which makes sense, because he came into this world moving fast and never really slowed down. Raised on a farm in Middleton, Wis., he learned early on how to work hard, play harder, and find joy in the simple things. He lived life entirely on his own terms, never much caring what other people thought about what he said or did - and that honesty (and occasional lack of filter) was a big part of his charm. That farm-boy grit and mischief stuck with him for life.

He graduated from Middleton High School in 1964 and went to college at UW-Whitewater for Business (mostly because everyone told him he couldn’t). He spent a long career as a salesman, loving life on the road, knocking on doors and making deals on the back of cocktail napkins.

He was always up for an adventure - on skis, riding a snowmobile, or cruising the lake on his beloved pontoon at their cabin up north. The Northwoods was his happy place - filled with campfires, UTV adventures, and more laughter than sleep. The time he shared at “Club Chuck” with his friends and neighbors at the cabin were some of the best times of his life.

Chuck loved a round of golf almost as much as the post-round cocktail with his buddies. Whether on the course or at the 19th hole, he was in his element - surrounded by friends, stories, and plenty of laughter.

Through it all, the true constant in his life was his wife, Beverly (Deitelhoff) Bollenbach, whom he married July 27, 1969. She was “a good-hearted woman in love with a good-timin’ man”, who not only put up with his wild side but joined in. Their journey together had its twists and turns, but through it all they were happy, sharing in adventures and building a life full of laughter and love.

He was a proud father to Chad and Todd and their wives, Jill (Hellenbrand) Bollenbach and Emily (Henken) Bollenbach, and an even prouder grandpa to his four grandkids - Mason (wife Sadie), Edie, Ethan, and Violet - who adored their fun-loving, larger-than-life Grandpa Chuck.

Chuck was preceded in death by his parents, Orvin and Vanita (Voss) Bollenbach; and his brothers, Paul and Lee Bollenbach. He is survived by his wife, Bev; his brother, Gary; his two sons and their wives; and four grandchildren who carry his spirit forward.

He’ll be remembered for the life he provided for his family and the good times he shared with everyone who knew him.

A visitation will be held at GUNDERSON WEST FUNERAL AND CREMATION CARE, 7435 University Ave., Middleton, from 2 p.m. until 5 p.m. on Thursday, October 16, 2025, immediately followed by a celebration of life at THE SPORT BOWL, 6815 University Ave., Middleton, from 5:30 p.m. until 8 p.m. Friends and family are invited to share stories and raise a glass to honor the original Good Time Charlie.

Online condolences may be made at www.gundersonfh.com.

Gunderson West
Funeral & Cremation Care
7435 University Ave.
(608) 831-6761

Charles John Bollenbach

May 08, 1946 - October 08, 2025

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