William (Bill) Patrick Dooley Sr., 78, died after a brave battle with esophageal cancer on Nov. 4, 2024. Born in Oak Park on Jan. 12, 1946, he grew up in River Forest, in the St. Luke Parish community, attended St. Luke Parish School, Fenwick High School, and Loyola University Chicago. Bill had his mother’s artistic talents and loved to draw as a child, creating countless cartoon characters and books that he would later share with his family, especially his grandchildren. His family was also musically talented. Singing was part of the fabric of his household, especially once they got hold of oldest brother Tom’s ukulele. Bill and his brothers’ love of harmony and playing music together truly blossomed. Together they sang barbershop, songs of the ’50s, folk music, and songs from Ireland. He was very proud of his Irish heritage and the spirit and joy that it provided.
During his college years, his songwriting took off as he became masterful on the 6-string and 12-string guitars, always by ear and feel. His intense focus and incredible memory allowed him to develop his unique style of fingerpicking and the ability to play anything after hearing it only once.
The music of the Kingston Trio, Bob Gibson, Bob Dylan, Gordon Lightfoot and many others inspired his songwriting. Bill and his brothers, Joe, Jim and Mike, formed an official band together and became a constant in the Chicago folk and Irish music scenes. The Dooley Brothers continued to sing, record, and write music for over 40 years. Bill’s favorites included “Little Willo,” “Black Sunshine,” and “Michigan Wind.” Bill also performed his own live shows, most notably at FitzGerald’s in Berwyn, where he was able to capture an audience with song and storytelling.
In 1969 he married Judy, his one and only. They shared many adventures, their biggest legacy being their five children and six grandchildren. They loved sitting by a good fire with Bill playing the guitar, a serious game of gin, or watching beautiful sunsets from their favorite spot in Pentwater, Michigan.
He loved being a father and created magic for his children with his clever storytelling, harmless mischief, imaginative play, inventions, creativity, Michigan hikes, explorations on the Chippewa Flowage, and of course, playing his guitar. He made every holiday extra special with his creative talents and his desire to create joy for his family. His patient, loving, and caring nature always made him a safe space to be and he kept that space boundlessly open to his family. Caring for his family was his number one priority. He loved nature and the stars, executed well-thought-out practical joke, appropriately timed movie quotes, and epic scary campfire story.
No visit to his grandchildren was complete without singing a few songs, including the ever-entertaining works of Shel Silverstein that always made them giggle. He shared stories and folktales, played games, made epic s’mores, taught them the art of the dribble sand castle, taught them magic tricks, and special happy birthday serenades.
He savored beauty and peace on a still lake with his fishing pole or riding his bike along Lake Michigan.
In 1972 he was among the first market makers of the Chicago Board of Options Exchange, where for over 40 years he crafted unique trading strategies and provided for his family. He had an excellent mind for creatively solving problems and fixing things, making him the neighborhood and family handyman. He loved inventing gadgets and things that would make life easier and more fun. He was a friend of Bill W. and many who knew him for over 47 years. His entire adult life, he carried in his shirt pocket a small notebook, in which he wrote songs, poems, ideas for projects, life’s lessons, and his ever-evolving prayer list.
Bill was the husband, best friend, and sweetheart of Judith Ann Dooley (Lynch) for over 55 years. He was known as Dad, Pops, Da, and P-Bear to his five children, William P. Dooley Jr., Emily (Jesse) Gallagher, Seamus (Erikah Lushaj) Dooley, Joseph (Liat Nosrati) Dooley, and Maria (Sean Duff) Dooley. He was Bapa and Grandpa Bill to his grandchildren, Ava, Tommy, Brighe, Hadley, Declan, and Kaia.
He was the son of Thomas Francis Dooley and Avis Grace (McMullin); the brother of Tom (Nancy) Dooley, Dennis (Kirste Carlson) Dooley, Joe (Katie Joyce) Dooley, Jim (Anna) Dooley, and Mike (Trish) Dooley; brother-in-law of Ed (Chris) Lynch and Tom (Judy) Lynch; uncle and great-uncle of Ben (Pam Turlow) Dooley, Tommy (Pam) Dooley, Danny (Trish) Dooley, John (Nancy) Dooley, Mo (Chris) Lanty, Peggy Lynch, Kevin (Paige) Lynch, Micky (Robert ) Hubanks, Ed (Maria) Lynch, Danny (Katie) Lynch, Mike Lynch, and Mick, Bridget, Jimmy, Maryrose, Maggie, Claire, Annie, Sean, and Grace Dooley.
Visitation will be held on May 3 from 10 to 11 a.m. at St. Luke Church, 7600 Lake St., River Forest, followed by a Celebration of Life Mass at 11.