William Joseph Callahan

William Joseph Callahan, known to his friends and family as Bill, passed away on January 14, 2025, at the age of 78. Born in Chicago on July 28, 1946, to William Joseph Callahan and Gloria Mallace Callahan, Bill spent his formative years in Hyde Park. He attended St. Thomas the Apostle grade school, Mt. Carmel High School, and later graduated from Loyola University, where he majored in English.

Bill’s first professional job was teaching English and Math at St. Thomas the Apostle School in Hyde Park. In parallel, he worked part-time as a bartender at the Woodlawn Tap, a position that would come to define his life for the next 56 years. Under the mentorship of its founder, Jimmy Wilson, Bill transitioned from bartender to manager, and ultimately became the owner of the beloved bar after Jimmy's passing.

The Woodlawn Tap, nestled in the heart of the University of Chicago community, was more than just a business to Bill. It was a place where he became known for his sharp wit, generosity, and unparalleled ability to connect with people. A true judge of character, Bill treated everyone with the same respect and kindness, regardless of their background. He was a stabilizing presence in the lives of many, with a remarkable capacity to listen and engage with both grand philosophical discussions and the everyday exchanges that made life feel richer.

Three years ago, Bill sold the business to his dear friend Matt Martell and retired, though he never quite lost the draw of the bar. He missed the lively conversations, the energy of being behind the counter, and the joy of connecting with friends old and new. He was a lover of baseball, an avid reader, and always open to book recommendations, eager to share his favorite stories and instill a love for good literature in his children. His greatest passion, however, was travel and food, particularly discovering new restaurants and bars. Bill’s love of good food and drink was matched only by his delight in sharing those experiences with family and friends. His legendary hours spent poring over the Zagat guide, discussing favorite spots or walking into unassuming eateries to see what they had to offer became a hallmark of his spirit. In his presence, one would never be short a solid belly laugh and easy, comfortable companionship.

Bill was preceded in death by his parents and his brother, Jim Callahan. He is survived by his wife of 55 years, Jan Hartley Callahan; his children, Will Callahan of St. Charles, IL, and Kristen Callahan Alyn of Pacific Palisades, CA; his son-in-law Scott; and his cherished grandchildren, Abby and Eddie Alyn, Harper and Emery Callahan. He also leaves behind his sister, Lauren Callahan West of Lexington, KY; his sister-in-law, Karen Hartley Standing of Richland, WA; and many loving nieces, nephews, extended family and the dearest of lifelong friends.

A memorial to celebrate Bill's life will be held on Saturday, March 22, 2025, from 1-4pm at the Woodlawn Tap, 1172 E 55th St, Chicago, IL. In lieu of flowers, the family requests that any photos, anecdotes, or stories about Bill be shared. These can be brought to the memorial or emailed to kristenalyn@gmail.com. Bill Callahan indeed had a life well-lived, filled with love, lots of laughter, and connection. He will be deeply missed by all who knew him.

Arrangements entrusted to Chicagoland Cremation Options of Schiller Park, IL