Harry Burns and Sally Albright spent twelve years, three months, and forty days trying to figure out if men and women can ever truly be friends without the sex part getting in the way. It’s a classic. But honestly, if you strip away the pecan pie, the wagon wheel coffee table, and the fake climax at Katz's Delicatessen, you’re left with a movie that lives and breathes through its music. The When Harry Met Sally OST didn't just support the film; it basically resurrected an entire genre of American music for a new generation. It made jazz standards cool again at a time when hair metal and synth-pop were still screaming for attention.
Think back to 1989.
Rob Reiner was on a hot streak, but he had a specific problem. He wanted the movie to feel timeless. He didn't want it to be anchored to the late eighties with a soundtrack full of gated reverb and drum machines. He wanted the New York of Gershwin and Rodgers and Hart. Enter a 21-year-old kid from New Orleans named Harry Connick Jr.
At the time, Connick was a virtuosic pianist who hadn't really broken into the mainstream consciousness. Reiner heard his tapes and realized he’d found his "Harry." Not the one on screen, but the one who would provide the soul of the film.
The Connick Effect and the Birth of a Classic
Most soundtracks are a compilation of various artists thrown together by a music supervisor to sell CDs. This was different. While the movie features icons like Ray Charles and Frank Sinatra, the When Harry Met Sally OST—the actual album released by Columbia Records—is almost entirely a Harry Connick Jr. showcase. It’s him, a piano, a bass, a drum kit, and occasionally a lush string section or a big band.
It’s intimate. It feels like a late-night set at a smoky club where the ice is melting in your bourbon and you’re wondering if you should call your ex.
Connick’s performance of "It Had to Be You" is the centerpiece. It’s the song that plays during that frantic New Year’s Eve run. It’s become so synonymous with the film that it’s hard to hear those opening piano chords without seeing Billy Crystal’s heavy knit sweater. But the album is deeper than just that one hit. You’ve got "Our Love is Here to Stay" and "But Not for Me." These aren't just covers. They are reinterpretations that respect the Great American Songbook while injecting a youthful, slightly cocky energy that mirrored Harry Burns’ own personality.
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The choice to go with jazz was a gamble. In 1989, the charts were dominated by Paula Abdul and Milli Vanilli. Dropping a record full of standards from the 1920s through the 1940s could have flopped hard. Instead, it went double platinum. It won Connick his first Grammy for Best Jazz Male Vocal Performance. More importantly, it set the template for the "Nora Ephron Movie" aesthetic: high-end Manhattan apartments, falling leaves in Central Park, and music that feels like a warm hug.
Why the Arrangements Matter More Than You Think
Let’s talk about Marc Shaiman. He’s the guy who did the arrangements for the film. Shaiman is a legend now—think Hairspray and Mary Poppins Returns—but here, he was working with Reiner and Connick to create a specific sonic palette.
The music is "source-adjacent."
That’s a fancy way of saying the music often feels like it's actually happening in the world of the characters. When Harry and Sally are walking through the Metropolitan Museum of Art, the music isn't just background noise; it’s part of the atmosphere. The arrangements on the When Harry Met Sally OST are famously "clean." There’s no overproduction. You can hear the wooden thunk of the double bass strings. You can hear the crisp snap of the snare.
- "Don't Get Around Much Anymore" gives us that uptempo, slightly cynical vibe that fits the early "we hate each other" phase of their relationship.
- "I Could Write a Book" captures the intellectualism of the characters—the way they overthink everything until it’s almost too late.
- "Let's Call the Whole Thing Off" is the playful banter translated into melody.
Interestingly, some of the best songs in the movie aren't on the official soundtrack album. It’s a common frustration for fans. Louis Armstrong and Ella Fitzgerald’s "Let’s Call the Whole Thing Off" is a cornerstone of the film’s charm, but due to licensing tangles that were common in the eighties and nineties, it didn't make the Connick-centric disc. The same goes for Ray Charles’ "Say No More."
If you’re a purist, you basically need two playlists: the official Harry Connick Jr. album and a "complete" list of the songs as they appear in the film.
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The Missing Pieces
If you want the full experience, you have to track down the versions used in the actual scenes. Sinatra’s "It Had to Be You" (the orchestral version) hits differently than Connick’s trio version. There’s a certain weight to Frank that Connick, as a young man, couldn't quite replicate yet. He hadn't lived enough. But that’s actually why Connick works for the movie—Harry and Sally are young, neurotic, and figuring it out. The music needed to feel fresh, not just nostalgic.
The Cultural Legacy of the Soundtrack
It is impossible to overstate how much this record changed the music industry's approach to romantic comedies. Before this, rom-coms often tried to be "current." Think about the soundtracks to movies like Pretty in Pink. They are great, but they are undeniably "80s."
The When Harry Met Sally OST proved that you could use "old" music to tell a "new" story. It paved the way for the Sleepless in Seattle soundtrack and eventually the explosion of standards-heavy scores in the 90s. It also essentially launched Harry Connick Jr. as a superstar. He wasn't just a jazz guy anymore; he was a heartthrob.
The album stayed on the Billboard Jazz charts for what felt like an eternity. It stayed there because it’s a perfect "dinner party" record. It’s sophisticated but accessible. It’s the kind of music that makes you feel like you’re living a much more interesting, articulate life than you actually are.
Factual Nuances: What Most People Miss
There’s a common misconception that Connick wrote the score. He didn't. The score—the instrumental bits that underscore the dialogue—was handled by Marc Shaiman. Connick performed the songs. It's a subtle distinction, but an important one for anyone looking at the technical credits.
Another weird fact? The "Winter Wonderland" sequence.
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It’s one of the most iconic visual moments in the film—Harry carrying the tree alone. The song choice there is vital. It’s Ray Charles. It adds a soulfulness that cuts through the potential cheesiness of a Christmas scene. This movie understands that romance isn't just about the "happily ever after"; it’s about the longing and the loneliness that comes before it. The soundtrack captures that duality perfectly. It’s both celebratory and deeply melancholic.
How to Experience the OST Today
If you’re looking to dive into this music, don’t just stream the top hits.
Listen to the album as a cohesive work. Start with "It Had to Be You" and let it play through to "Where or When." Notice the pacing. The way the album transitions from solo piano flourishes to full-band swing reflects the messy, evolving nature of Harry and Sally's relationship over those twelve years.
Actionable Steps for the Collector and the Fan:
- Find the Original Vinyl: If you can snag a 1989 pressing of the Columbia record, do it. Jazz of this era was recorded with high fidelity in mind, and the warmth of the piano sounds significantly better on an analog setup than a compressed MP3.
- Build a "Complete" Playlist: Create a folder or playlist that integrates the Connick tracks with the Sinatra, Ray Charles, and Ella Fitzgerald tracks used in the film. It provides a much more narrative-driven listening experience.
- Watch for the "Big Band" Cues: Pay attention to the track "Stompin' at the Savoy." It’s a masterclass in how to use percussion to drive a scene's energy without needing a single word of dialogue.
- Check the Credits: Look for the name Bobby Colomby. He produced the album. He was the drummer for Blood, Sweat & Tears, and his ear for production is why the record sounds so crisp and timeless even 35 years later.
The When Harry Met Sally OST remains a gold standard. It’s a reminder that sometimes, to move forward and create something that lasts, you have to look back at what worked before. It’s not just a collection of songs; it’s the heartbeat of a story about two people who took forever to realize they were perfect for each other.
To get the most out of your listening, compare Connick’s version of "But Not for Me" with the Chet Baker version. You’ll see exactly how Connick and Reiner were trying to brighten up the "sad jazz" trope to fit a comedy. It’s that specific tension—between the old-school cool and modern-day neurosis—that makes the soundtrack an essential piece of American pop culture history.
No other romantic comedy soundtrack has ever quite matched its influence. It didn't just sell albums; it changed the way we expect love stories to sound. Whether you're a jazz aficionado or just someone who likes a good story, this soundtrack is a mandatory listen. It’s basically the musical equivalent of a perfectly tailored blazer: it never goes out of style.
Next Steps for Deepening Your Knowledge:
- Research Marc Shaiman’s Later Work: See how his experience on this film influenced his work on The American President and A Few Good Men.
- Explore the Great American Songbook: Use the tracklist as a jumping-off point to discover the original versions by Gershwin or Cole Porter.
- Compare Film vs. Album: Watch the movie and note which songs are used as "background" versus which ones are "featured." It’s a great lesson in film scoring.