Diann Elaine Crowley, 79, of Madison, WI, passed away May 19, 2026, at Sun Prairie Senior Living in Sun Prairie, WI. Diann was born on Jan. 2, 1947, in Merrill, WI, the daughter of Raymond and Florence Rehwinkel. She was raised on a farm, a life she loved and spoke of often. She graduated from Merrill High School and moved to Madison. 

She married James W. Crowley, Jr. on Nov. 1, 1991, and lived in Madison's University Heights neighborhood. Summers were spent at the Crowley Cottage on Lake Waubesa. Diann thought it was fantastic to have a place only 20 minutes away where she could get away from it all. 

Diann started her career working every tax season at H&R Block. She later worked for Stafford & Neal as a bookkeeper. The World Dairy Expo in Madison was a large part of Diann's life. She worked there for many years and made many friends - in fact, that's where she met Jim. 

She and Jim enjoyed Badger sporting events and spending time with friends. Diann combined those passions by hosting tailgate parties for every Badger home football game while also providing parking for guests a few blocks from Camp Randall Stadium. 

Diann was an outgoing person, with a great laugh and smile, who talked to everyone and became friends with many of them. She liked going to new places and meeting new people, usually with an array of friends and drivers. 

Diann is survived by her children, Derek (Kim) Schuette and Danita (Gary) Lehnherr; grandchildren Thomas (Jaqueline Neves) Schuette, Katherine (fiancée Bradyn Eldridge) Schuette, Carson Lehnherr and Rowan Lehnherr; her brother Peter Rehwinkel; nieces, nephews, and other relatives; grandson of the heart, Bryan (Ally) Earleywine and their children Clara and Chloe; and many friends. She was preceded in death by her parents, her husband Jim, and her grandson Cole Lehnherr. 

A celebration of Diann’s life will be held from 4:00 to 6:00 p.m. on Friday, June 5, 2026, at the Big Ten Pub on Regent Street in Madison. 

Memorial gifts may be made to the James Crowley Sr. Dairy Management and Extension Fund at the University of Wisconsin Foundation. Please make checks payable to UW Foundation -- Crowley Dairy Fund and mail them to UW Foundation, US Bank Lockbox 78807, Milwaukee WI 53728. To make an online gift, go to supportuw.org/giveto/crowleyfund. Memorials may also be made in Diann's name to The River Food Pantry at www.riverfoodpantry.org. 

The family would like to thank the staff at Sun Prairie Senior Living for their professional care during Diann's stay. 

Please share your memories of Diann by posting in her guestbook.

Cress Funeral & Cremation Service

3610 Speedway Road Madison

(608) 238-3434