Anniversaries: Chicago ‘85… The Movie by Dave Hollister
Dave Hollister was best known for his gospel-honed vocals and a stint as Blackstreet’s original lead singer, but this sophomore solo effort would become his best work to date.
As a Chicago native, Dave Hollister chose “‘85” to signify a pivotal year in his life—1985—when a family secret upended his world. That was the year teenage Dave discovered that the man he’d grown up calling father was in fact his stepfather. The revelation was earth-shattering, triggering anger and rebellion in the young Hollister. “That’s when I found out my father was actually my stepfather,” he recalled in a 2000 Billboard interview with Gail Mitchell, “I rebelled, doing some hustling and gangbanging. But I was able to turn things around.” Hollister’s ability to overcome those turbulent years would later fuel the redemptive themes of Chicago ‘85. The album was a sonic memoir of that journey—from confusion and street temptations to responsibility and faith. Hollister has said he hopes his story can inspire others facing similar struggles, noting that if he can help just one kid realize they can make it out, he’s accomplished something. That earnest sense of mission underpins the album’s storytelling.
Chicago ‘85… The Movie picks up where Hollister’s 1999 gold-certified debut Ghetto Hymns left off, further blending the sacred and the secular. Raised in the church (his father was a minister and family friend of soul legend Donny Hathaway), Hollister always infused his R&B with gospel passion and “kept it real” lyrical testimonies. He wasn’t interested in chasing trends or gimmicks; Hollister aimed to “get at the humanity of contemporary urban experiences”. On Chicago ‘85, that meant laying bare his own experiences as a young Black man in Chicago—the good, the bad, and the ugly. The album is structured loosely like a film (complete with an opening “Interlude (I’m Not Complete)” and a closing reprise of the same theme), inviting us to watch Hollister’s life unfold scene by scene. Throughout these songs, he inhabits the role of a soulful storyteller, conveying cautionary tales and confessions with a preacher’s conviction.
What makes the record especially compelling is the balance it strikes between grit and romance, street smarts and soul. Hollister’s narrative voice was undoubtedly shaped by surviving the violence and vice of his youth, but by 2000, he was also a married man determined to do right. “My wife was with me through the whole process this whole, and that made me more comfortable. I’m in love, and the songs I sing on the new album are basically about that,” Hollister said of recording Chicago ‘85. Love—particularly the trials and triumphs of committed relationships—is the central theme that emerges. In real life, having his spouse’s support gave Hollister a newfound stability, and in his music, he translates that into songs that celebrate family and loyalty even as they grapple with the temptations that can undermine them. The result is an album that feels lived-in and honest: part love letter, part cautionary tale, delivered with the raw intensity of a Sunday sermon and the smooth swagger of classic ‘90s R&B.
To bring his autobiographical songs to life, Hollister enlisted top-notch collaborators, including some with Chicago roots. He worked with homegrown talent Steve Huff—a Chicago-based producer known for his success with R&B singer Avant—and rising star Mike City, who had just made waves producing Carl Thomas’s hit “I Wish.” These producers helped frame Hollister’s story in a rich musical backdrop. Huff in particular understood the Chicago vibe and gave the project an authentic local flavor. He produced the lead single, “One Woman Man,” crafting it into a radio-ready mid-tempo groove that bridged street sensibility with church-bred soul. Mike City, for his part, co-wrote “One Woman Man” and produced the bumping track “Keep On Lovin’ Me,” imprinting his signature blend of funk and melody. Together, the likes of Huff, City, and other contributors (Tim & Bob’s lush arrangements, Chucky Thompson’s funk sensibility, and even newcomer Tank’s songwriting on a couple of tracks) made Chicago ‘85 a diverse yet cohesive sonic movie. Each song’s production complements the narrative: sometimes dramatic and orchestral, other times stripped-down and gritty, always centered on Hollister’s powerful, husky baritone. As Hollister’s label noted at the time, “we’ve assembled an array of hot producers who have completed an incredible album”—an album that truly plays out like the soundtrack to his life.
This record offers plenty of other standout moments that illuminate different facets of Hollister’s story as the single anchors the album’s theme of commitment. “Keep On Lovin’ Me” is one such gem—an anthemic mid-tempo groove that showcases Hollister’s appreciation for a ride-or-die woman. Over a “solid mid-tempo slammer” beat polished by Mike City’s production, Hollister sings about a lover who has seen him at his worst and still stands by him. He admires this woman’s loyalty “even when she curses [him] out and makes [his] bail”—a wry, vivid line that hints at rough patches with the law and arguments in the relationship, all weathered through love. The song’s infectious hook and upbeat swing belie the drama in the lyrics; it feels like a celebration of that strong, no-nonsense partner who keeps Hollister grounded. On “Destiny,” Hollister turns up the cinematic flair. This slow-burning ballad is draped in “swirling string arrangements” courtesy of producers Tim Kelley and Bob Robinson (aka Tim & Bob), giving it the feel of a classic soul epic. Hollister’s vocals soar to near-operatic heights, emphasizing the song’s grand romantic drama.
Perhaps the rawest chapter of Hollister’s story comes in “Doin’ Wrong.” Co-written with the late Chucky Thompson, the track lays down a “funky stop-and-go guitar/bass riff” that immediately nods to vintage funk and soul. Hollister uses that gritty funk backdrop as his confessional pulpit. He directly confronts his own failures as a man and partner, essentially indicting himself before anyone else can. The song opens with a brooding, bluesy vibe, and Hollister’s voice is almost pleading, conveying guilt and frustration. As the groove builds, he recalls the warnings from his mother that he’d end up “just like [his] father” if he strayed. In a powerful lyrical moment, he sings that his mom always told him he would “sleep just like him, creep just like him, cheat just like him”—a devastating admission that he has fallen into the very cycle of infidelity and dishonesty he witnessed growing up. It’s a rare thing in R&B at the time (or any time) to hear a male singer lay his faults so bare, and Hollister does it without excuse, only a desire to do better. His vocal performance is fevered and intense—as if he’s sweating out a deep shame.
Hollister’s expedition of repentance reaches a heartfelt resolution on “I Don’t Want to Be a Hustler.” Placed near the album’s conclusion, this track is an open apology and a final act of closure for the narrative. Over a chugging, head-nodding rhythm, Hollister plainly states his determination to leave the street life behind. It is written almost like a letter to his mother, the very person he feared he might disappoint. He “spells it all out” here, directly apologizing to his mom for the hustling and gangbanging of his youth and admitting that “he wasn’t raised that way.” The production (helmed by Vidal Davis, with a subtle mix of live bass and programmed drums) keeps things simple, ensuring the focus stays on the message. There’s sincerity in Hollister’s gravelly voice, slightly cracking with emotion, repeats the refrain, “I’m sorry, Mama, I tried to be a better man.” It’s not hard to draw a line from this song back to that fateful moment in 1985—the young Hollister, angry and astray, now coming full circle to acknowledge his wrongs and make amends. In the context of the album, “I Don’t Want to Be a Hustler” is the emotional climax, in which the protagonist fully rejects the lure of the streets.
Hollister’s blend of street storytelling and church-trained soul was part of a larger lineage in Black music. One can hear echoes of Marvin Gaye’s introspection and Donny Hathaway’s testifying spirit in the album’s DNA. Upon its release, Hollister’s style drew comparisons to contemporaries like Gerald Levert, and indeed, both singers mined the complexities of love and life with gospel fervor. Yet Hollister carved out his own niche. In the wake of Chicago ‘85, a new wave of artists like Jaheim and Tank arrived, clearly taking cues from Hollister’s soulful realism. The album lets us hear that movie play out: youthful mistakes, a redemption arc, a celebration of hard-won love. It’s that sincerity and narrative cohesion that keep his sophomore so vital. As Hollister sings in the soaring “I’m Not Complete,” he implies that his story—like all of ours—is still blossoming. Amid the “baby mama dramas” and “thug-life odes,” Hollister communicates a rare authenticity with his clearly expressed lyrics, making the album feel as thrilling and real as life itself. The power of Hollister’s voice and story still hits home—that actual soul music only gets richer with time, aging like a fine wine from the cellar of R&B history.