Death arrives with regularity, but sometimes it can produce something in addition to tears. And so it was last week when Mike Dooley let me know that his brother, Jim Dooley, had died on Aug. 8 after a lengthy battle with colon cancer.
“Jim was a talented musician, superb vocalist, brilliant guitarist,” Mike wrote in a message, along with his son Mick and Jim’s daughter Claire. “And a prolific songwriter, poet, artist, nature photographer, husband and father.”
Sad for a moment, then I smiled, as I was tossed back in time.
Jim, Mike, Joe and Bill were The Dooley Brothers band, as entertaining and durable as any band in the city’s musical history. They have been at it since the 1960s, a duration that earned them the title, bestowed by an NPR voice, of “the longest continuously running band in the Chicago area after the Chicago Symphony Orchestra.”
I first saw them at … well, I don’t remember the exact spot or year. It could have been any number of places because this band’s list of previous venues played represents a sort of history of clubs and saloons. Here are a dozen, so let your memories flow: The Abbey, Amazing Grace, Barbarossa, The Bulls, Byfield’s, Earl of Old Town, Holstein’s, Saddle Club, Stretch’s, Backroom, Four Farthings … and on and on.
They performed at FitzGerald’s in Berwyn when the club opened in 1980 and played at the club’s St. Patrick’s Day party for four decades. They played at libraries, festivals, senior centers and country clubs — thousands of gigs.
I wrote about them nearly 40 years ago, when they had been in the music business for 20 years. They were playing at the bygone Roxy when Jim told me, “It’s been difficult to pin a label on us … We were always open to all forms of music and like to think we grew more diverse, independent of the scene around us.”
Never difficult to appreciate and admire, the Dooleys were children of River Forest. There was one grandfather who performed Irish ballads on Lake Michigan cruise ships and another who was a fiddler in his native Ireland before joining the Cicero fire department. Their parents were Thomas Dooley, a photo engraver at this newspaper, where he composed and set the colors for the Sunday comics, and Avis, a portrait artist with a studio on Michigan Avenue.
The family home was filled with music, and the brothers taught themselves to play and recorded songs on a reel-to-reel tape recorder.
As he started in college in 1966, Jim, along with brothers Joe and Bill, founded their original musical group. They named it The Dooley Boys and started playing at colleges and various coffeehouses and nightclubs in and around Chicago, notably in the club-peppered Old Town and Rush Street neighborhoods. Youngest brother Mike joined a few years later and the band became The Dooley Brothers.
They were never easily categorized but rather open to many styles. Jim explained that after they first visited Ireland in 1977, “We were really exposed to traditional Irish music. And we fell in love.”
They focused on that sound for a while, playing a six-month engagement at the bygone Kilkenny Castle Inn on the Northwest Side. “But then we started sneaking in swing music and then it was back to the old mixed bag,” said Jim.
That became one of the principal joys of this band, their eclectic taste. Folk, jazz, swing, folk … they could do it all, and recorded it on four albums. The first was jazz-rock, the second all-Irish. And the third? “Next, we’d like to come out with a swing album,” Jim told me years ago at the Roxy. “And then an album or original tunes. And if we’re not really famous in five years, we’re going to become baseball players.”
They never did become famous (or rich), but they kept playing, as they married and had children and were often joined on stages by other local performers and eventually by more family members.
In reviewing the group, I wrote, “(The band) provided a generous mix of Irish tunes, light jazz, swing, do-wop and blues. It was all sentimental and accessible stuff, but it was done with such forceful harmonies, clever arrangements and frequent instrumental flourishes that it was surprisingly fresh and entertaining.”
Brother and band member Bill Dooley stopped performing a while back and died in November 2024.
The band had by then been bolstered by Mike’s son Mick, who joined in 2015. In the wake of Jim’s death, he wrote of his uncle, in part, “Jim’s legacy will echo throughout his social circles and beyond, in the thousands of souls he touched in performance and friendship, those good times they had, living life, feeling the good vibrations of live, local music at bars. Singing, dancing, laughing with real people. Experiences that can’t be outsourced to social media.”
Jim’s daughter Claire, born to wife Anna, began playing with the band in 2020 and she says, “The honor of my life has been performing with my dad on stage, playing guitar with him at our house, and our voices harmonizing together. As our voices harmonized together, so did we.”
There’s a new album that has been in the works, and there will be a celebration of life for Jim sometime in the coming months. There will be, it goes without saying, music and tears. Memories and smiles, too.
