Dolly Parton belonged to the world, but for a few memorable months in 1991, Chicago got to claim a little piece of her.
Parton came to the city to film the romantic comedy Straight Talk, spending months living and working in Chicago for a movie that made the city far more than a backdrop. Nearly two decades later, when asked about the experience, her memories remained remarkably warm.
“I had one of the best times of my life,” Parton recalled in a 2011 interview with Windy City Times.
Then, in quintessential Dolly fashion, she summed up Chicago even better.
“It is a great city. Even when it’s cold, the people are still warm.”
Dolly comes to Chicago
Released in 1992, Straight Talk starred Parton as Shirlee Kenyon, a small-town Arkansas woman who leaves her troubled life behind and heads to Chicago, where a misunderstanding lands her behind the microphone at a radio station. Her plainspoken advice quickly turns her into a local celebrity.
James Woods co-starred as newspaper reporter Jack Russell, who begins investigating the suddenly famous radio personality and, inevitably, falls for her. Watch the trailer below:
Principal photography began in Chicago in July 1991, with the production filming throughout the city and in Lemont. Chicago wasn’t disguised as somewhere else. The bridges, streets, buildings and skyline were integral to Shirlee’s story of arriving in a big city and finding an entirely new life.
Recognizable locations included the Wabash Avenue Bridge over the Chicago River and the Field Museum. A building at Lincoln, Marshfield and School represented the fictional WNDY radio station.
The film also included several performers with strong Chicago connections. Michael Madsen, who grew up in the Chicago area, played Shirlee’s boyfriend Steve. Chicago P.D. actor and theater veteran Amy Morton appeared in the film, while a young Ron Livingston, then working in Chicago theater, made his feature-film debut in a small role.
And while making the movie, Parton found herself in one particularly unlikely corner of Chicago’s music scene.
Dolly at the Rainbo
During the Straight Talk shoot, Parton performed at the Rainbo Club in Wicker Park, the neighborhood bar that would become closely associated with Chicago’s alternative music scene.
The performance was connected to a scene in the film, but the image remains irresistible. Dolly Parton, already an international country music superstar, taking the stage at the Rainbo in Wicker Park while spending her summer making a movie in Chicago.
It was one of those wonderfully unexpected intersections that the city’s film and music worlds occasionally produce.
A relationship that lasted for decades
Straight Talk may have given Parton her most substantial connection to Chicago, but it was hardly her first.
She had been performing for Chicago-area audiences since at least the 1970s, appearing over the years at venues including the Ivanhoe Theatre, Rosemont Horizon, House of Blues, Chicago Theatre and Ravinia.
She returned in January 2011 for the Chicago opening of the national tour of 9 to 5: The Musical, for which she wrote the music and lyrics. During that visit, Parton looked back on the months she spent here making Straight Talk and spoke so affectionately about the city.
Her final Chicago-area concert came in August 2016, when she brought her Pure & Simple tour to a sold-out Ravinia.
But Parton’s Illinois legacy ultimately extended well beyond stages and movie sets.
A legacy measured in books
In 2023, Illinois began a statewide expansion of Parton’s Imagination Library, the childhood literacy program Parton founded in 1995 in honor of her father, who never learned to read or write.
The program mails free, age-appropriate books every month to participating children from birth to age five.
That connection continues to grow. In August 2026, Illinois celebrated the five-millionth book mailed through Dolly’s Imagination Library in the state. The program now reaches more than 111,000 Illinois children and families across 95 of the state’s 102 counties.
For someone whose public life was built around songs, movies and an unmistakable personality, it may be one of the most meaningful measures of what Parton leaves behind.
Chicago has plenty of memories of Dolly Parton. There are the concerts, the movie locations, the summer she spent filming on our streets, the unexpected night at the Rainbo and even a mural of her that remains in Edgewater.
But perhaps the best remembrance comes from Dolly herself.
Years after Straight Talk wrapped and she had moved on to countless other stages, cities and adventures, she still remembered those months in Chicago as “one of the best times of my life.”
And she remembered why.
“Even when it’s cold, the people are still warm.”
Chicago was lucky to have a little piece of Dolly, and her warmth will remain part of the city she remembered so fondly.
