If you were hanging out in Brooklyn or Boston around 2016, you probably heard it. That infectious, genre-blurring thump. It was the sound of a band finally deciding to stop playing by the rules of "cool" indie jazz and just embrace the weirdness of pop. I'm talking about Lake Street Dive Side Pony, an album that, looking back a decade later, serves as the definitive pivot point for Rachael Price and her crew.
It wasn’t just a record. It was a manifesto.
The title refers to a hairstyle, sure. But for the band—Rachael Price, Mike "McDuck" Olson, Bridget Kearney, and Mike Calabrese—it was a metaphor. It was about choosing to be eccentric. It was about that specific type of confidence where you know something looks a little bit ridiculous, but you rock it so hard that everyone else starts wondering why they’re being so boring.
Why the Side Pony Concept Was a Massive Risk
Before 2016, Lake Street Dive was the darling of the conservatory circuit. They met at the New England Conservatory of Music. They were technical wizards. They could out-swing, out-play, and out-harmonize almost anyone on the road. But with the release of Lake Street Dive Side Pony, they deliberately stepped away from the "retro-soul" box people had built for them.
They traded some of that upright-bass-driven jazz purity for synthesizers and dance beats.
Dave Cobb produced it. Yeah, that Dave Cobb—the guy known for stripping things down to the bone with Chris Stapleton and Jason Isbell. You’d think putting a Nashville "truth-teller" producer with a bunch of jazz school nerds would result in a folk record. Nope. Instead, they went to RCA Studio A and made something that sounded like 1970s AM radio mixed with a modern dance party.
Honestly, some old-school fans hated it at first. They missed the acoustic simplicity of Bad Self Portraits. But the band didn't care. They were leaning into the "Side Pony" philosophy: "We're doing this because it feels good, not because it fits the brand."
The Tracks That Defined the Era
You can't talk about this album without talking about "Call Off Your Dogs." It's basically a masterclass in how to use a pentatonic scale without sounding like a blues cliché. Bridget Kearney’s bass line in that song is absolute insanity. It’s busy, it’s melodic, and it carries the entire track while Rachael Price does things with her voice that shouldn't be legal.
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Then there's "I Don't Care About You."
This song is the epitome of the album's attitude. It’s snarky. It’s upbeat. It’s a breakup song that sounds like a celebration. Most bands try to sound "meaningful" by being slow and sad. Lake Street Dive decided that being meaningful meant being honest about the relief of finally not giving a damn.
- "Hell Yeah" brought a grit they hadn't shown before.
- "Close to Me" proved they could still do the ballad thing better than anyone else, but with a shimmering, slightly psychedelic edge.
- The title track, "Side Pony," is literally a song about a haircut, yet it functions as a rallying cry for individuality.
It's weird. It's funky. It's uniquely them.
Breaking Down the Dave Cobb Influence
Cobb is famous for capturing "the moment." He doesn't like overdubbing a thousand takes. He wants the grit. For a band as technically proficient as Lake Street Dive, this was a challenge. They were used to being perfect. Cobb pushed them to be loud and a little messy.
The drums on the record sound massive. Mike Calabrese transitioned from a jazz-influenced "touch" player to a guy hitting the backbeat like his life depended on it. You can hear it in the snare crack on "Main 0n End." It’s visceral.
They used vintage gear—analog synths that hissed and buzzed. They stopped trying to sound like a pristine live recording and started trying to sound like a record. There is a difference. A live performance is about the energy in the room; a record is about the atmosphere in your headphones. Lake Street Dive Side Pony was the first time they truly mastered the atmosphere.
The Cultural Impact: From Niche to Late Night
Before this album, Lake Street Dive was playing clubs. After it, they were on Stephen Colbert, Ellen, and The Today Show.
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The visual aesthetic shifted too. Suddenly, there were bright colors, vintage polyester, and, yes, actual side ponies. It gave the audience permission to stop being "serious" music listeners. You didn't have to analyze the subdominant chords anymore—though they were still there if you wanted to look. You could just dance.
They tapped into a specific vein of 2016 culture that was tired of overly processed EDM and equally tired of "stomp and holler" folk. They found the middle ground. It was sophisticated pop for people who actually liked instruments.
The Technical Brilliance Nobody Talks About
We need to talk about the arrangements. Mike "McDuck" Olson’s trumpet work on this album is subtle but essential. He isn't playing big, flashy lead lines. He's layering textures.
The vocal harmonies are another beast entirely. Most bands use a backing track for those lush, three-part harmonies. Lake Street Dive does them live, into one or two mics. On the album, you can hear the natural phase of their voices blending together. It’s a "Wall of Sound" technique that feels human because you can hear the slight imperfections in the breath.
- They tracked much of it live.
- They prioritized the "vibe" over the "grid."
- They let the bass dominate the mix, which is a very Motown move that modern pop usually ignores.
What Most People Get Wrong About This Record
People call this their "pop" album like it's a bad thing. Or they think it was a departure from their roots.
Actually, it was a return to them.
The band grew up listening to the Beatles, Hall & Oates, and Sly and the Family Stone. Those artists weren't trying to be "genre-specific." They were just trying to write great songs. Lake Street Dive Side Pony was the band finally having the budget and the confidence to sound like their influences without filtering them through a "jazz school" lens.
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It wasn't a sell-out move. It was an "all-in" move.
Lessons from the Side Pony Philosophy
If you’re a creator, there’s a lot to learn here. The biggest takeaway? Don't be afraid to outgrow your original audience. If Lake Street Dive had stayed in the acoustic-soul lane, they probably would have plateaued. By embracing the Side Pony—the "weird" choice—they expanded their horizons and found a way to stay relevant for another decade.
They proved that virtuosity doesn't have to be boring. You can be the best musician in the room and still play a song that makes people want to jump around.
How to Appreciate Lake Street Dive's Mid-Career Masterpiece
To truly get what they were doing, you have to look past the kitsch. Start by listening to the album on high-quality headphones. Ignore the irony of the title and focus on the architecture of the songs.
- Listen to the Bass Lines: Bridget Kearney is the secret weapon. On tracks like "Mistakes," her playing is essentially a lead guitar part played an octave down.
- Study the Lyrics: Beneath the upbeat tempos, songs like "Godawful Things" are actually quite dark and complex. They hide the medicine in the candy.
- Watch the Live Versions: Go find the "Live at the Current" or "NPR Tiny Desk" sessions from this era. You'll see that the "pop" production wasn't a mask—they could back up every single note without the studio magic.
The best way to honor the legacy of this era is to apply that same "Side Pony" energy to your own life. Do the thing that feels a little bit "too much." Wear the metaphorical hairstyle that makes you stand out. The world has enough people trying to fit in; it needs more people willing to be a little bit off-center.
If you haven't revisited the record lately, put it on and skip straight to "Can't Help Who You Love." It’s the perfect distillation of everything they got right: heart, soul, and a whole lot of rhythm.
Final Takeaways for the Super-Fan
If you're looking to dive deeper into the technical side of the band's transition during this period, check out the interviews Kearney gave to Bass Player magazine around 2016. She talks extensively about the switch from a traditional upright sound to a more processed, "electric-mimicking" upright tone that defined the record. Also, look into McDuck’s blog posts from that era—he was always incredibly transparent about the gear and the terror of changing their sound.
Ultimately, this album remains a high-water mark for mid-2010s indie music because it refused to be cynical. It was earnest, it was loud, and it was unapologetically fun. In an era of shoegaze and irony, that was the bravest thing they could have done.
Check out the vinyl pressing if you can find it; the analog warmth does wonders for Cobb's production style, especially on the low end. It's a reminder that great music doesn't just happen—it's engineered by people who aren't afraid to look a little bit silly for the sake of a great hook.