Ashley Cooke Gives Rosemont Fans a Night of Heartbreak, Nostalgia and Raw Storytelling

Ashley Cooke brought her Baby Blues Tour to Joe’s Live, once again reuniting with her Chicago-area fans.

By

Madeleine O’Connell

| Posted on

October 7, 2026

at

9:33 am

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Ashley Cooke; Photo by Matt Leddo

Ashley Cooke brought her Baby Blues Tour to Illinois on Thursday, Oct. 1, turning Joe’s Live in Rosemont into a sea of blue as fans packed the venue just outside the city of Chicago.

Prior to stepping on the stage at 9 p.m., Cooke set the tone for the night by offering a nostalgic introduction with “Since U Been Gone” karaoke-style as the lyrics scrolled across old television screens on stage. The screams of excited fans indicated that they were warmed up and ready to sing along with Cooke’s catalog.

Making her grand entrance with upgraded lighting and production elements from previous tours, the rising star launched into a lively performance of “Excuses” before moving through a mix of fan favorites, including “I Almost Do,” “Sleepless in Seattle” and “Swear Words.” With these tracks, she gave the first taste of the playful, heartbreak-fueled energy that would carry on throughout the night.

Ashley Cooke; Photo by Matt Leddo
Ashley Cooke; Photo by Matt Leddo

This wasn’t Cooke’s first time performing in the area and it certainly won’t be the last. She told the crowd about her previous shows at Joes on Weed St., offering “full transparency” as she admitted that she loves to play Chicago.

“I hope to keep playing Chicago for the rest of my career. I just love you guys so, so much. And it’s always so good to be here,” she stated. “Seriously, it means the world that y’all are in this room tonight. You guys could be quite literally anywhere tonight and you guys chose to be here, to buy the ticket, to care about my music and I really just means the word. So thank you guys so much for being here. We’re going to have a damn good time.”

Regardless of whether fans in attendance had seen one of Cooke’s previous Windy City shows, it’s safe to say Thursday night’s performance was one to remember. One of the standout elements of the night was the creative use of audio snippets throughout the set, including messages from family, friends and fellow artists, as well as iconic moments from TV history.

At one point, a clip of Ross and Rachel’s famous “we were on a break” argument from Friends played before Cooke launched into “The Hell You Are,” perfectly setting up the song. She also continued the tradition of adding a recorded voicemail in the midst of her song “xs.” This message was recorded by a Chicago fan named Jake who had something important to say about his ex.

“If there was one thing I’d say about my ex is that I thought our relationship was like a Chicago Bears touchdown with fireworks but at the end of it all, it just ended up being smoke in the air,” he stated over the speakers.

Later in the show, Cooke’s sister, Jenn Cooke, left a few of her own pre-recorded messages, serving as introductions to several songs like “johnny ‘n june” and “the girl who cried wolf.” Cooke also brought the crowd into the fun when one of her band members grabbed the VHS camera and searched the audience for couples to feature on the “Kiss Cam” during “never til now.” The moment came after Cooke joked about her own dating life and then encouraging couples to dance together or challenging her single fans to find someone to do the same with.

One of the most sing-along-worthy moments of the night came when the songstress decided to go back to the music she grew up loving as a ’90s baby. She delivered a medley of hits from the era, including LeAnn Rimes’ “Can’t Fight the Moonlight,” Hilary Duff’s “Come Clean” and Avril Lavigne’s “Sk8er Boi.” As she performed, grainy images of Cooke’s childhood appeared on the vintage TV screens behind her, leaning fully into the nostalgic moment.

But the night wasn’t all about the high-energy moments. Ashley Cooke also slowed things down a bit for “it’s been a year” and “if I’m being honest,” sitting down with just her guitar and allowing the vulnerability of the songs to take center stage.

The latter of the two tracks serves as the opening track on Cooke’s new self-titled album that arrived in August. She explained that the decision to name the album after herself was connected to the raw authenticity woven throughout the project, giving fans a chance to get to know “Ash the person” beyond Ashley Cooke the artist. She also credits “if I’m being honest” as the song that truly kickstarted the project.

“I wrestled with different names for the project, but it wasn’t until I sat in my living room with two of my oldest co-writer friends drinking way too much wine and just venting about our deepest, darkest secrets and the things that scare us to say out loud about ourselves that we wrote this song and it became the first song on my self-title album. And it just feels like the most of me I’ve ever been in a song in a project. And so I just want to say thank you guys for loving this project. And this song is really kind of what started it all.”

Ashley Cooke; Photo by Matt Leddo
Ashley Cooke; Photo by Matt Leddo

The momentum came back up when supporting act McCoy Moore joined Cooke onstage for a cover of Rascal Flatts “Summer Nights.” Sadly the night came to a close shortly after, with the final songs of her main set being “High School Sweetheart” and “Dance Around It.” Cooke returned for an encore featuring “Your Place,” her first No. 1 at country radio, and “Baby Blues,” during which she invited a brave audience member with blue eyes to move closer to the stage so she could sing directly to him, making for a memorable end to the evening.

“Thank you for always showing up for me in Chicago. I could not love y’all more,” she said before making her way off stage one last time.

The Rosemont stop felt like a night built around relatable experiences, raw storytelling and a true glimpse into Ashley Cooke as both an artist and a person with feelings poured out in her music. She gave fans plenty of reasons to dance and sing, but also created space for the heartbreak, nostalgia and stories behind the songs to resonate.

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.