Olivia Rodrigo and Chappell Roan's "expectations" Remix Drops Tonight: What to Know + My First-Listen Headphone Pick

Olivia Rodrigo's "expectations" remix featuring Chappell Roan, plus its music video, arrives tonight, Oct 15, at 5 PM PT. Chloe covers what's new, why this pairing is such a big deal, and her pink Bose pick for a first listen.

Bose QuietComfort Headphones in Petal Pink.

Okay, friends, cancel your Thursday night plans. Olivia Rodrigo's "expectations" remix featuring Chappell Roan, and its official music video, drop tonight, Thursday, October 15, at 5 PM PT / 8 PM ET. Two of the biggest voices in pop on one track? This is the crossover episode we've been waiting for, and I've been refreshing my pre-save like it owes me money.

What's actually happening

Olivia announced the remix on October 13, a day after teasing it on her Instagram Stories with a voice clip (presumed to be Chappell's) saying, "Ooh, Olivia does remixes now." Here's the rundown, per Universal Music Canada and NYLON:

  • It's Olivia's first-ever remix. (Quick jargon check: a remix is a reworked version of a track that's already out. A feature is when another artist guests on it.)
  • Dan Nigro produced it. He's a longtime collaborator of both artists, so this one is basically a family reunion.
  • There's a music video. It stars both of them and was directed by Bardia Zeinali. Olivia shared a photo from the set: the two of them in '80s-style tutus on top of a vintage car, Chappell in her signature white makeup and Olivia with a very big bow. I am obsessed.
  • Physical copies are a thing. Limited-edition 7" vinyl, CDs and cassettes are up for pre-order on both artists' stores. Cassette girlies, this is our moment.

Why this pairing hits so hard

The original "expectations" comes from Olivia's third album, you seem pretty sad for a girl so in love, released June 12. The album debuted at No. 1 on the Billboard 200 with 485,000 first-week units, the biggest solo debut of 2026, according to Universal Music Canada. Per the song's Wikipedia page, she wrote "expectations" with Amy Allen and Dan Nigro, and it's pure '80s new wave and synth-pop. (New wave is that shiny, synth-heavy, dance-y sound from the late '70s and '80s. Think big drums, bigger hair.) It debuted at No. 20 on the Billboard Hot 100, and Pitchfork called it a contender for song of the summer.

And these two go way back. Chappell opened for Olivia on the GUTS world tour in 2024, and she was on the lineup for Olivia's all-women Daisy Chain Fields festival in Irvine this August. Watching two artists go from opener and headliner to a duet is honestly my favorite kind of plot twist.

My first-listen headphone pick

A song this layered deserves better than laptop speakers. For a pink-coded pop moment, there's really only one choice:

Bose QuietComfort Headphones (Petal Pink, Limited Edition). They're over-ear with active noise cancelling, which is tech that listens to the noise around you and cancels it out, so every synth and harmony comes through. Quiet and Aware modes let you switch between full noise cancelling and hearing what's around you. Adjustable EQ in the Bose app lets you turn up the bass for that new-wave drum sound. You get up to 24 hours of battery, and if you forget to charge them before 5 PM, a 15-minute USB-C charge gets you up to 2.5 more hours. They also come with an audio cable, so you can listen wired even if the battery runs out. And they're pink. Obviously.

My game plan for tonight

Pre-save now, charge your headphones this afternoon, and at 5 PM PT, hit play on the video first. Then listen to the original and the remix back to back and see what changed. I already have a group chat ready for the debrief.

If you want new headphones for the occasion, they're linked above and ship fast from right here in California, with next-day delivery across the continental US. See you in the replay count, friends!


Chloe Hall is one of Frontrow's editorial voices, a character our team writes as to bring a pop fan's perspective to the gear news we cover.