If you, like me, are a millennial or older who is trying to be Hip With The Kids On TikTok, you may have noticed over the past few years a deep reverence for older musical artists taking flight. At least on my FYP, I'm just as likely to see Gen Z-ers gushing about the likes of Jeff Buckley or Alice in Chains as I am Doja Cat or Taylor Swift. There's a nostalgia for by-gone aesthetic trends they barely lived to see, too, from Y2K to Tuscan interior design and more. I chalk this up, like pretty much everything happening culturally in 2026, to the digital age: young people yearn for a time where style was more personalized, rather than curated by an algorithm trying to maximize views, likes, and revenue. There was a sense of authenticity and genuine creativity that can often get lost as today's acceleratingly-corporatist America seems more interested in following a formula than developing something new. There's also, of course, the oft-discussed fact that smartphones and social media have in many ways isolated us from those nearby, weakening our sense for real human connection and forging an increasingly-lonely society.
Ever since her mainstream breakout at the age of 17 with "drivers license," Olivia Rodrigo has been Gen Z's biggest figure in the pop music landscape. Fittingly, her music captures her generation's penchant for looking backwards culturally and pulling those influences to the modern day. 2021's SOUR and 2023's GUTS both found their musical footing in 2000's pop rock, influenced by and compared to the likes of Paramore, Avril Lavigne, and Lily Allen. However, Rodrigo has always managed to combine those older sounds with a current perspective - she writes of romance in ways best understood by those who grew up in a world of dating apps and Instagram DM's.
For her third album, you seem pretty sad for a girl so in love, Rodrigo has retained that current lyrical point-of-view, but musically she's turned the clock back even further - trading her iPod for a Walkman, the sk8r bois for the goth kids. Most obvious is the album's three nods to legendary alternative outfit The Cure: lead single and album opener "drop dead" references their 1987 hit "Just Like Heaven"; second single "the cure" is, of course, the name of the band (and was released on World Goth Day); and singer Robert Smith hops on "what's wrong with me" to become the first featured artist across Rodrigo's three albums to date. Rodrigo and main collaborator Dan Nigro branch further into 80s post-punk and college rock flavors on "maggots for brains" - which sports a New Order-esque guitar riff - and "purple," which is built around a repeated lyric of "melt with you," calling back to Modern English's signature 1982 track. Even structurally, you seem pretty sad bucks streaming-era trends; the album is fifty minutes long, no song is under three minutes, "the cure" is five minutes long with no single edit made available, and closer "cigarette smoke" nearly reaches six minutes.
All that said, the narrative Rodrigo spins across you seem pretty sad is undeniably youthful. Split into two halves - appropriately, "girl so in love" and "you seem pretty sad" - it details the full arch of a relationship from internet crush to wishing she could forget. "drop dead" opens with Rodrigo "stalking" her love interest on social media and testing their astrological compatibility. "u + me = <3" bears a text-lingo title, and "my way" sees Rodrigo calling out another woman for "posting another pic in clothes that I know are his." Across the first seven tracks that make up the "girl so in love" half, she's completely smitten.
Things change drastically on "the cure," the first track of the "you seem pretty sad" section and the album's emotional center. Surrounded by strummy acoustic guitars building to a string-laden cathartic finale, Rodrigo details how this relationship has uncovered her wounds (which, on "honeybee" earlier, she had claimed were healed). "I thought I found the antidote with you / But my head is full of poison, and my heart is full of doubts," she cries out. Her conclusion? "It don't matter how your love feels anymore / it'll never be the cure." The repeated refrain of "I'm unraveled" really tells the whole story. Compared by many to "Tonight, Tonight" by Smashing Pumpkins, "the cure" crystalizes everything Rodrigo's music has represented across her three albums, and in this humble blogger's opinion, has quickly becoming the crowning jewel of her discography.
From there, the relationship is in tatters. A brutal three-song stretch of "begged," "what's wrong with me," and "less" sees Rodrigo broken and despondent. The quiet restraint of "begged" still cuts deep with its chorus' closing statement: "nothing's quite enough when I know that to get it I begged." Robert Smith is a welcome guest on "what's wrong with me," though it is funny to hear him sing a verse that, while emotional, was clearly originally written with the 23-year-old Rodrigo in mind rather than a 67-year-old who's been married since 1988. Throughout this second suite, only "expectations" feels more like a spunky "fuck off" than a bitter "fuck you." It's the most self-reflective and downtrodden we've ever seen Rodrigo; rather than "onto the next one," this time it feels like she's tired of trying. The final moments of the album have her wishing the memories could "go dark."
With how emotional you seem pretty sad is, it's remarkable how catchy Rodrigo & co have made the album. The bright-eyed "drop dead" and the confessional "the cure" have both been stuck in my head since the singles dropped. "maggots for brains" has a delightfully bright chorus, and "expectations" is still fun despite coming in the album's latter, darker half. Rodrigo's voice is as compelling as ever, from the tongue-in-cheek spoken-word verse of "drop dead" to the delicate balladry of "honeybee."
There's more cooks in the kitchen helping this time, too; while GUTS was almost exclusively written by Rodrigo and Nigro, you seem pretty sad credits a number of songwriters. Steph Jones joins the fold for the first time on "my way," having worked previously on two of the decade's greatest pop hits in JADE's "Angel of My Dreams" and Sabrina Carpenter's "Espresso," Amy Allen, who did contribute to GUTS-era numbers "pretty isn't pretty" and "scared of my guitar" (as well as also working on "Espresso"), appears on five different tracks. Sasha Alex Sloan, known for working with Charli XCX on sister tracks "Track 10" and "Blame It On Your Love," shows up on "what's wrong with me." And rising producer Jim-E Stack, fresh off producing Lorde's Virgin, co-produced "purple," and his flourishes are noticeable.
Speaking of Lorde - there's a through line connecting her sophomore effort Melodrama to you seem pretty sad for a girl so in love. Much like Rodrigo, Lorde broke out in her teens with a pop record that eschewed what was stylistically popular at the time. She then returned with Melodrama, a matured tale of progressive heartbreak assembled with a key collaborator in Jack Antonoff. It became a flagship breakup record for younger Millennials; time will tell if you seem pretty sad can be the same for Gen Z a decade later. One thing is for certain, though: three albums in, Olivia Rodrigo keeps getting better, and continues to build her legacy as the voice of a generation.
