Michael Thomas Bailey

Michael Thomas Bailey, 50, of Madison, formerly of Sheboygan, passed away peacefully at his home on Saturday, February 29, 2020.
Born April 10, 1969 in Sheboygan, Michael was a son of Thomas L. and Jill M. Canisius Bailey. He attended Sheboygan area schools and graduated from Sheboygan North High School in 1987. He continued his education at the U.W. Milwaukee and finished his Masters degree in Educational Administration from the U.W. Whitewater.
Mike served as the Dean of Madison Media Institute in Madison. Prior to joining the education field, he had a career in the music industry, starting as an independent label owner, Star Star Stereo, and later worked in New York City for Blue Note, a blues label within EMI Music. He was a Grammy-voting member of the National Academy of Recording Arts & Sciences and served on various advisory committees, including the Dane County Arts Commission, the Sunset Music Series in Madison and WVMO 98.7 FM community radio for the city of Monona. He worked with many artists over the years, including The Neville Brothers, The Blind Boys of Alabama, Roseanne Cash, and Alejandro Escovedo. Mike was known as "Old Man Jukebox" and formed many close relationships over the years through his passion for music. He was a self-described educator, record collector, concert goer, food lover, music industry exile and facilitator of good things.
He is survived by the love of his life, Andrea "Andie" Hartwig, Madison; his parents, Thomas and Jill Bailey, Sheboygan; his brother, Eric (Leigh Anne Staley) Bailey, Whitefish Bay; his sister, Laurie (Shawn) Szecsy, Lake Mills; his niece and nephews, Emma Staley-Bailey, Colin Staley, Sawyer & Parker Szecsy; his cousins, Tammy (Jeff) O'Keefe Kriedler, Sheboygan, Thomas O'Keefe, Sheboygan, and Edward & Marjorie Canisius, Sheboygan; other relative and many friends. He is further survived by Andie's family including her mother, Erika Hartwig, Greenville, and her sister, Monica and Scott Mageland and their children, Sam and Taylor; and his beloved dog, Tweedy.
Besides his grandparents, he was preceded in death by an infant sister, Michelle Bailey, and his aunt and uncle, Judy and Thomas O'Keefe.
Funeral services for Mike will take place at 6:00 p.m. on Thursday, March 5, 2020 at the Olson Funeral Home & Cremation Service, 1132 Superior Avenue, Sheboygan. The Rev. David Van Dixhorn will officiate. Family and friends are welcome at the funeral home on Thursday from 4:00 p.m. until the time of service. Interment will take place in Woodlawn Cemetery.
A memorial fund has been established in his name. Cards and donations may be mailed to the funeral home at 1132 Superior Avenue, Sheboygan, WI 53081.
The Olson Funeral Home & Cremation Service has been entrusted with Mike's arrangements.