James ‘Boz’ O’Brien, owner of the Reilly’s Daughter tavern in Oak Lawn, dies at 75

If ever a man seemed born to run a tavern, that man was James “Boz” O’Brien, and he ran one of the finest this city has ever known.

A native of the Mount Greenwood neighborhood, he was only in his mid-20s when he opened a small tavern in a strip mall at 111th Street and Pulaski Road in Oak Lawn. He called his place Reilly’s Daughter and over the next decades, as it grew in size from 1,400 square feet to more than 5,000, it became not only an oasis of food and drink but a place of frequent parties, celebrations, music and events large and small, the sort of gatherings that help define and knit a community together.

O’Brien died on Jan. 28 at age 75. His death was confirmed by his son, Brendan O’Brien.

A wake took place at the Curley Funeral Home in Chicago Ridge, a funeral mass at St. Cajetan Catholic Church and burial at Holy Sepulchre Cemetery. The crowds were multi-generational and memories plentiful.

“It was something to see,” Brendan O’Brien said. “It showed how many lives my dad touched.”

A good tavern is more than a place to get a drink or seek shelter from the bumps and troubles of the world. A good tavern levels life’s playing field, becoming a space where an alderman can talk to a cab driver. It is a place where you can reassure or comfort yourself in conversations about matters large and small. It is a place where good fellowship is not on the menu but in the air. Such was Reilly’s Daughter, which was named for an old folk song popularized by the Clancy Brothers that begins: “As I was sitting by the fire, eating spuds and drinking porter, suddenly a thought came into my mind, I’d like to marry old Reilly’s daughter.”

“Boz held that place together. He was a larger-than-life character, Irish to his core and personality,” said his longtime friend and customer Mike Houlihan.

The bard of the South Side as writer, actor, newspaper columnist and filmmaker, Houlihan shared a personal example, saying, “I had moved home to Chicago after a dozen years in New York City, that was fun, but with a wife and twin sons I needed steady work, which I was lucky enough to find in Chicago through the old South Side Irish network. A steady paycheck was a glorious thing, but I was starting to feel that old itch to get back on stage.”

He talked to O’Brien and was encouraged to write a play about his youth and he “helped put some dough together to produce it.” The result was “Goin’ East on Ashland,” which opened at the Beverly Arts Center in the early 1990s. “It was an instant hit with critical raves and sell-out crowds and ran for over six years all over Chicagoland,” says Houlihan. “I never would have taken that leap of faith if Boz hadn’t believed in me.”

Others have stories too. Boz was an ebullient and energetic storyteller and conversationalist. He was also a great and talented connector of people. With friends from all areas of work and life (and seemingly all ages), he was artful at finding jobs for people, arranging events and running the liveliest of taverns.

O’Brien was born Feb. 15, 1950, to parents Lawrence and Margaret O’Brien, and attended Queen of Martyrs Elementary School and Brother Rice High School. He opened Reilly’s Daughter in 1976.

His was a family-friendly place and you could walk in on any night and run into pals and politicians, neighbors and labor leaders, or, for a time, members of the 1986 Super Bowl Bears. You might see Notre Dame coach Lou Holtz hosting a live TV show. There were frequent charity events, and music, music, music from Irish bands and with regularity from Lightning & Thunder, the Milwaukee-based Neil Diamond tribute band dramatized in the new movie “Song Sung Blue.”

Reilly’s Daughter held live turkey raffles for Thanksgiving, and wildly competitive soda bread and Irish coffee competitions. Santa Claus arrived by helicopter for some Christmases and the San Diego Chicken was hired to appear and strut along the bar. And on and on, because O’Brien was a master of creative stunts. And was the easiest of soft touches, but one who never tooted his own horn.

It can be an exhausting life too, and, having opened a small oasis inside Midway airport in 2002, O’Brien sold the original spot the next year and tried to take it easy, moving his two sons into managerial duties.

The space operated for a time with new names and new owners before O’Brien and his sons, Brendan and Danny, took it over in 2015, and a new generation of customers has come calling.

“Dad was always around,” said Brendan O’Brien. “He really did love people. And my brother Danny and I grew up in this world. Whether it was here or he was coaching our teams, he was a hands-on father, very involved in our lives. He was always around, always doing stuff for us and other people. But it wasn’t just about having fun. My father was one of the hardest workers I have ever known or seen. And that has really shaped us and the way we live, and work.”

Things could often get pretty noisy inside Reilly’s Daughter. But Boz never worried about that, saying, ever with a smile, “Our next-door neighbor is St. Casimir cemetery, so there’s never been a noise complaint.”

Survivors include sons Brendan and Dan O’Brien; and siblings Sheila McNulty, Paula Litman, Kevin O’Brien, Larry O’Brien and Caron Hayes; as well as a grandchild and nieces and nephews. Services have been held.

rkogan@chicagotribune.com