2000 Rewind: Remembering Dave Hollister’s Chicago 85 … The Movie

Y’all ready to relive Y2K? All year long the Rewind column will revisit the year 2000, celebrating great releases that will mark 25 years in 2025. I’ll be joined by a host of old friends as we look back at a new millennium of music.

Twenty-five years ago today, the world of R&B was blessed with a gem. While it wouldn’t achieve the massive sales success or mainstream kudos as many of the other albums we’ve featured this year, Dave Hollister’s Chicago 85 … the Movie would go on to achieve cult fame in R&B circles. Essentially, if you really know R&B ball, you know this album. Speaking of someone who knows R&B, Brandon O’Sullivan aka THEO returns to Soul In Stereo to celebrate Dave’s best moment.

Let’s get started – share your early memories of Dave and this album.

Brandon: Before we start, my initial introduction to Dave Hollister was technically “Before I Let You Go” by Blackstreet that played at a Publix, but in terms of his solo material, it was more “My Favorite Girl” because of BET’s Top 25 Countdown that used to air on a Saturday (I couldn’t even pinpoint who hosted that episode). I have to give the ultimate thanks to my late mentor Harris, who put me onto a lot of R&B albums in the 2000s, and Chicago ’85 was one of them. What trips me up is hearing “One Woman Man” because I heard it in passing before I took a deep dive into this record, as I was already curious about what he’d sound like bound by an entire body of work. Over time, it became one of those projects I’d play when I needed something steady, whether to clean the place, sing along, or just reflect. Once you start to get older and have responsibilities with real-life commitments, some of the songs land differently. I can honestly say that the record matured with me.

Edd: I know I’ve told this story before, but hey I’m an old head, and if it’s one thing old heads love to do, it’s repeat themselves!

Picture it: It’s summer 2000 and I’m working at Babbages, the mall video game chain that y’all know today as Gamestop. It’s midday and, as usual for that time of year, the mall is pretty empty. In walks a guy who wanted me to help him pick out a few new games.

That wasn’t an usual request – people stopped by all the time looking for new hotness. But this brother was buying a lot of stuff, not just one game. I’m hanging with him the whole time he’s shopping, just randomly chatting about things. When it’s time to ring him up, he whips out his credit card and, as was customary back then, I asked to see his ID. He shows it to me and I say, “Wait a minute? DAVE!?” He belly laughs, hype that he ran into a fan.

(He asked for a discount, I was like playa please. Yes, I playa pleased Dave Hollister.)

We chatted some more, he left the store, he came back to chat again for a bit, and before leaving the mall for good, swung past one last time to wave. To this day, my friends still say that Dave Hollister is MY biggest fan.

Needless to say, after years of interviewing and interacting with tons of artists for this site, meeting Dave is still my No. 1 celebrity encounter. And once I got my hands on his sophomore album just a few months later, it hit even harder. The same down-to-earth personality that resonated through all those songs wasn’t an act – I had witnessed it in real life.  It really was Dave.

By the summer of 2001 I’d make the biggest transition of my life at that point – graduating college, then moving 1,000 miles away to start a new career in a new city – and Chicago 85 was my soundtrack during that transformative time.

Yeah, this album means a lot to me.

What’s your top song, and why?

Brandon: “One Woman Man”

I rank this signature song as the album’s standout thanks to Mike City: “One Woman Man.” It’s a stripped-down mid-tempo groove that has Hollister singing to a woman who’s flirting with him, but politely declines because he’s going home to his partner, a mature response that wasn’t common in mainstream R&B, and definitely needs more of that. The way he alternates between flirtation and firmness boundaries shows his storytelling skill (his underrated asset we rarely discuss), and his smoky tone oozes sincerity. But there’s depth in the voice and delivery. I love how Hollister doesn’t go overboard. He doesn’t need to shout or dramatize; he states his truth, “I finally have settled down,” and the honesty in his tone carries weight. That combination of simplicity and conviction hits the mark. When I hear it, I’m not just hearing a love song—I’m hearing a decision, a stand. And in a world of love songs that swing between hot and cold, this one stands firm. For me, it’s the emotional core of the album.

Edd: “One Woman Man”

There’s a reason why “One Woman Man” has become Dave’s signature song. The storytelling: Even without a video, your mind’s eye paints a picture of this encounter perfectly. The personality: Dave feels like a real human being – admitting his past sins, even a few current weaknesses, all while fighting to stay loyal to his lady. The passionate performance: Dave’s vocals have never been questioned, but even when most would rely on the production and witty lyrics to carry the load, Dave STILL gives it his all in the booth. It’s the perfect marriage of style and substance – the blueprint for a hit single.

With so many great songs here, we should have gotten another single. Which one would you have chosen?

Brandon: “We’ve Come Too Far”

To be honest, you can pick any of the three-track run of “We’ve Come Too Far,” “You Can’t Say,” and “Yo Baby’s Daddy,” and I would’ve agreed with you. I would’ve rolled with “We’ve Come Too Far,” as it has that build, that cinematic energy, that makes you sit up. Produced by the same duo that gave us “Thong Song” during that era with Tim & Bob, it starts out soft, then layers on instruments, voices, and passion that give you goosebumps. Plus, the theme of enduring conflict to salvage a troubled relationship resonates with someone who’s grown. I know it’s an early-2000s ballad, but it can be radio-friendly.

Edd: “Don’t Take My Girl Away”

There are several decent contenders for singles glory. “You Can’t Say” is one of those midtempo pops that R&B Voldemort made popular in this era, and of course I’ll always ride for a power ballad like “I’m Not Complete” but there’s something about “Don’t Take My Girl Away” that feels like a good fit for both midday playlists and the Quiet Storm corner. The production is more subtle than most radio hits, but Dave’s fiery performance keep it from being a snoozefest. Add a strong visual treatment of Dave making one last effort to save his relationship and this could have been a winner.

What’s the most underrated song?

Brandon: “Destiny”

“Destiny” is the one I feel doesn’t get talked about enough. When I listen, it doesn’t hit you like the singles right away, but through and through, you’re caught up in its flow and vulnerability. It’s the kind of R&B track you find on your own, and then it becomes one of your private favorites. For me, it’s a hidden gem inside an already strong record.

Edd: “I’m Not Complete”

Remember those underrated album cut ballads that are so beloved today? I’m talking Dru Hill’s The Love We Had,” 112’s “Sweet Love,” etc.? That’s what  “I’m Not Complete” reminded me of – a song that might not land No. 1 on the 106 & Park countdown, but it’s THE shining example of an artist’s vocal talent. Dave’s performance is on another level (I still get chills hearing those final notes) and deserves to be mentioned among the best of its era.

What’s the best written song on the album?

Brandon: “Take Care of Home”

I always pick “Take Care of Home” primarily because of the message. The songwriting conveys a sense of valuing home, love, and responsibility (‘cause chasing nightlife and status can erode your relationship). Still, it doesn’t feel preachy, urging men to prioritize their families—a message that’s sadly more prevalent now. It feels honest and lived. For Dave, singing “I’m a living witness” reminds you that someone has lived this life, not just imagined it. The structure, the hook, the lyrics: everything earns its place.

Edd: “Take Care of Home”

Yeah man, Theo nailed this one. Usually in this era, songs like this are an opportunity for haters to pounce on broken relationships (between “I Wanna Know” and “All the Things” I’m definitely looking at you, Joe). But in this case, Dave spits OG wisdom, using his own mistakes as a warning for those who may be walking in his footsteps. It’s not preachy, it’s purposeful.

Also that line about him holding his girl’s hand while walking in the mall always reminds me of the day he stopped by my store, so there’s that.

Vocally, Dave is a beast. Which song best showcased his amazing vocals?

Brandon: “I’m Not Complete”

If I’m picking one where Hollister really leans into his full vocal arsenal, “I’m Not Complete” (full version, of course) takes it. He starts subtly and builds (with Tank in the backgrounds before he went trappin’) to those powerful layers where you feel the emotion unfold and expand.

Edd: “I’m Not Complete”

After I the way I gushed over “I’m Not Complete” above this should be a no-brainer. Theo’s right, the way this song builds to a stunning climax is what sets it apart. Each note is an outpouring of emotion, a performance so strong that it feels like the rafters are shaking by the end of the track. When I complain that modern R&B lacks legitimate passion, it’s because THIS was the type of track I was raised on. Dave makes you FEEL.

This album has been celebrated as a gem in R&B circles, but it never got the mainstream acclaim it deserved. Why do you think that is?

Brandon: Several factors limited the album’s mainstream impact. When Dave’s sophomore LP dropped in November of 2000, R&B was crowded with big looks and landmark releases from big names, including Jill Scott, Musiq Soulchild, Carl Thomas, D’Angelo, and Toni Braxton. The competition for radio slots and marketing dollars was fierce. For an album that was rooted in grown-man themes of loyalty, responsibility, and home that doesn’t revolve around flashy club bangers or crossover pop hooks might’ve been less marketable to the wider pop audience. Also, while the singles were solid (“One Woman Man,” “Take Care of Home”), they didn’t dominate the pop charts in the way that some peers did. So despite the quality, the timing and framing limited its broader visibility. And maybe the themes hit more immediately than widely. It’s the kind of record you grow with rather than an instant pop explosion.

Edd: Timing is everything and Dave was just the victim of a crowded market. The neo-soul crew of D’Angelo and Jill Scott already dominated the year, with Musiq Soulchild dropping his celebrated debut a week before this one and Erykah’s highly anticipated sophomore record landing THE SAME DAY as Chicago 85. Carl Thomas, Craig David, and That OTHER guy with an “I Wish song” – R&B was still extremely competitive and poor Dave just was drowned out by bigger, flashier acts and an emerging new subgenre of R&B. I could see an album of this caliber doing much better in the late 00s  when the playing field was more level (but before the R&B bubble burst in the 2010s). The problem wasn’t the content, it was the competition.

 How does this album rank among the best R&B projects of the 2000s?

Brandon: For me, among 2000s R&B projects, it’s one of the clear standouts, and even though there’s a lot of those underappreciated ones during that era, it belongs in the top 20 to 25 area. It may not have the impact or footprint compared to the other big guns, but its consistency, mature storytelling, and church-infused vocals make it one of the decade’s essential listens for me, especially among the handful you keep returning to when you’re after depth and feeling.

Edd: In terms of sheer quality, the homie Dave takes a backseat to no one. Even in a decade bursting with top-tier R&B, I think Chicago 85 holds its own. But as Theo mentioned, what truly holds it back is its lack of impact on the industry. It quickly, and sometimes unfairly, was overshadowed by higher-profile releases. But it probably deserves a top 20 mention at the very least. Considering all the heat we got that decade, that’s still very high praise.

Is Chicago 85 … the Movie Dave’s best album?

Brandon: Compared to his debut, which I enjoy heavily, the production is more polished, the storytelling more vivid, and the vocals even more soulful. While later albums such as Things in the Game Done Changed and his gospel projects have their moments (also the sequel Chicago Winds is massively slept-on), Chicago ’85 remains his crowning achievement and a high point for 2000s R&B. It’s a grown-man R&B album that balances street narratives with heartfelt domestic themes, something that’s been missing in execution for a minute. Even if it never dominated the mainstream headlines like the charts these kids love to bring up for validation, it remains a benchmark for mature contemporary R&B. If someone asks me to hand them one Dave Hollister album, this would be it.

Edd: Without question. Dave boasts a pretty strong discography – Things in the Game Done Changed, Chicago Winds, The MANuscript (very underrated by the way) and especially Ghetto Hymns all hold up exceptionally well today. But there’s something special about Chicago 85 –  the production, the writing, Dave’s peformances, the stars aligned to give him that one great, career-defining solo release that he deserved. Nearly everything Dave has touched is good, but Chicago 85? It’s GREAT.

Who do you agree most with, Brandon or Edd? Share your thoughts about it great album below.