Jackson Dean Rocks Milwaukee: On The Back Of My Dreams Tour

The energy in Milwaukee was electric as fans poured into The Rave for Jackson Dean's stop on the On The Back Of My Dreams Tour. Known for his raw, soulful voice and gritty storytelling, Dean has quickly built a reputation as one of country music's most compelling rising stars. His ability to connect with listeners through songs that feel both deeply personal and universally relatable has made this tour a highly anticipated event for his growing fan base.

The Rave, a historic venue with its iconic architecture and intimate yet lively atmosphere, served as the perfect backdrop for the evening. As concertgoers filled the space, the buzz in the air was undeniable. Groups of friends and families chatted excitedly, sharing their favorite tracks and speculating on what the setlist might hold. Fans young and old, from diehard followers to newcomers curious about the hype, were all drawn together by the promise of a night of unforgettable music.

Milwaukee’s The Rave, part of the historic Eagles Club building, stands as a monument to decades of music, culture, and community. Opened in 1926, this iconic structure originally served as a social and athletic club, boasting features like a bowling alley, swimming pool, and ornate ballrooms. Over the years, it transitioned into a premier entertainment venue, maintaining its architectural charm while becoming a cornerstone of Milwaukee’s live music scene.

Throughout its history, The Rave has hosted a wide range of artists, reflecting its ability to adapt to different genres and generations. From rock to hip-hop, country to EDM, this is a place where fans have gathered for nearly a century to celebrate their favorite sounds. For those in Milwaukee and beyond, The Rave isn’t just a venue—it’s an experience, a place where memories are made, and music becomes unforgettable.

Photos By: Aaron R. Shriver Photography

The evening’s opener, Nashville singer-songwriter Meg McRee, set the stage with a performance that felt both personal and powerful. Known for her skillful storytelling, she brought a mix of heartfelt lyrics and an authentic country sound to her set. With her fiancé, Ben Chapman, joining her on guitar, the chemistry onstage added a special layer of connection that resonated with the crowd.

Meg kicked things off with Usually You, a song that showcased her knack for weaving emotions into her music. Her voice, clear and emotive, drew the audience in right from the start. The set continued with Gone As It Gets, If I’m Lucky, and Say You Love Me, each track offering a glimpse into her artistry. Her ability to turn everyday experiences into relatable songs was evident, creating moments where the crowd swayed along in unison, captivated by her melodies and lyrics.

A standout moment of her set came with Red Yellow Indigo. Fans embraced the song wholeheartedly. It was the kind of song that lingered, leaving the audience humming its chorus long after the last note. Meg’s only cover of the night, Mamas Don’t Let Your Babies Grow Up to Be Cowboys, was a nod to the classics, and her rendition carried a warmth that felt both nostalgic and fresh.

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She closed her set with the soulful Mary Jane & Chardonnay, a perfect ending that encapsulated the essence of her performance. As the last chord rang out, the crowd erupted in applause, clearly moved by the honesty and heart she brought to the stage. Her set was more than an opening act; it felt like a celebration of her journey as an artist and a glimpse of her bright future.

Jackson Dean hit the stage to a roaring crowd, his first-ever performance at The Rave having already exceeded expectations. Originally slated for the smaller basement room, the show’s upgrade to the larger club-level space spoke volumes about the enthusiasm surrounding his tour. Wasting no time, Dean kicked off the night with Still Ragin’, immediately drawing the crowd into his gritty, unfiltered world of country rock. The energy stayed high with back-to-back performances of Duct Tape Heart and Trailer Park; each song delivered with a rawness that matched the electric atmosphere of the venue.

Pausing briefly to connect with his audience, Jackson invited the crowd to sing along if they knew the words, a gesture that only fueled their excitement. Fearless came next, and the crowd eagerly took him up on his invitation, their voices at times outmatching his own. Big Blue Sky followed, setting a tone that was both anthemic and personal. When he introduced Superstitions, Meg McRee joined him on stage, their voices weaving together seamlessly in a performance that showcased their chemistry and mutual respect as artists.

Despite pushing through some vocal strain—audible as he introduced 1971 with a cough and an admission that it might be a challenge—Dean powered on, bolstered by the audience, who sang louder and louder in support. Tracks from his latest album, *On The Back Of My Dreams,* were met with enthusiasm, particularly Real Real, Train, and Jane, each offering a preview of the bold and honest songwriting that fans have come to love. When Dean launched into Heavens To Betsy, he noted its rising place on country radio charts, and the crowd responded with deafening cheers, their energy matching his as he gave the song everything he had.

He shifted gears briefly with the poignant Wings, allowing the audience a reflective moment before promising to bring things home with a string of powerhouse tracks. True to his word, 49 Tons of Diesel Locomotive roared through the room, its intensity leaving fans breathless as he declared, Now that’s Rock N Roll. With his Maryland roots proudly acknowledged, he introduced Sweet Appalachia, a song that paid homage to his upbringing and showcased the depth of his storytelling. Dedicating Daddy Raised to the fathers in the audience, Dean brought a heartfelt touch to the set, which resonated deeply with the crowd.

Closing out with his breakthrough hit Don’t Come Lookin’, Jackson was joined on stage by co-writer and producer Luke Dick, a surprise that thrilled fans and brought the night to its climax. The song’s raw energy and driving rhythm had the crowd singing every word, a perfect capstone to the main set. Answering the raucous calls for more, Dean returned for an encore, performing Heaven and Another Century before bidding Milwaukee goodnight. It was a performance filled with heart, grit, and connection, leaving no doubt that Jackson Dean’s star is only continuing to rise.

Jackson Dean’s performance at The Rave was a night to remember, filled with powerful music, heartfelt moments, and an undeniable connection between the artist and his fans. The combination of his raw vocals, engaging storytelling, and a setlist packed with crowd favorites created an unforgettable experience. Meg McRee’s impressive opening act set the stage beautifully, building the excitement for what was to come. The energy of the audience, coupled with the intimate vibe of the historic venue, made the night feel incredibly special. Fans left the show not just entertained, but deeply moved, carrying the memories well beyond the evening.

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Jackson Dean Set-List:

Still Ragin’

Duct Tape Heart

Trailer Park

Fearless

Big Blue Sky

Superstitions

1971

Real Real

Train

Jane

Heavens To Betsy

Wings

49 Tons Of Diesel Locomotive

Sweet Appalachia

Daddy Raised

Don’t Come Lookin’

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Heaven

Another Century