Carly Simon has always been a bit of an enigma wrapped in a silk scarf and a killer melody. Honestly, if you only know her from the "You’re So Vain" mystery, you’ve basically missed the best parts of her career. People love to fixate on who the song is about—Warren Beatty? Mick Jagger? A composite of every ego-driven guy in the 70s?—but focusing on the subject is like looking at a Picasso and only wondering what the model’s phone number was.
The real magic is in the writing. It’s in the way she turns upper-middle-class anxiety into something that feels like a universal truth.
The Hits You Know (And Why They’re Better Than You Remember)
You can't talk about the best of Carly Simon without starting with the big guns. "You're So Vain" is the obvious entry point. But have you actually listened to it lately? The bass line, played by Klaus Voormann, is practically a lead instrument. It’s menacing. It’s cool. It’s the sound of someone who has finally stopped being intimidated by a man’s reputation.
Then there’s "Anticipation." We’ve been conditioned by ketchup commercials to think of it as a waiting-game anthem, but it’s actually a nervous, jittery song about the terror of a new relationship. It’s about that moment when you’re so happy you’re scared to death it’s going to end.
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The Essential Power List:
- "That’s the Way I’ve Always Heard It Should Be": This was her debut single in 1971. It’s incredibly dark for a pop song. It questions the entire institution of marriage at a time when that wasn't exactly the "done" thing for a rising star.
- "Nobody Does It Better": Arguably the best Bond theme ever recorded. Produced by Richard Perry and written by Marvin Hamlisch and Carole Bayer Sager, it perfectly captured Simon’s ability to be both vulnerable and incredibly powerful.
- "Coming Around Again": This 1986 hit from the movie Heartburn proved she wasn't just a 70s relic. It’s a song about the cyclical nature of life and pain, and it still hits like a ton of bricks.
Why Her 1975 "Best Of" Is a Masterclass
In 1975, Elektra released The Best of Carly Simon. It’s a triple-platinum beast of a record. It gathers the high points of her first five albums, and it’s arguably the most cohesive way to understand her early evolution.
You’ve got the playful "Mockingbird" duet with her then-husband James Taylor. It’s fun, sure. But then it’s followed by "Haven't Got Time for the Pain," which is a soul-searching meditation on recovery and moving on. The juxtaposition is jarring in the best way. She wasn't just one thing. She was the woman who sang about "Clouds in my coffee" and the woman who wrote "Legend in Your Own Time," a song that basically deconstructs the myth of the rock star while she was living inside it.
The Deep Cuts You’re Probably Skipping
If you want to be a true connoisseur of the best of Carly Simon, you have to dig past the radio edits.
Take "We Have No Secrets" from the No Secrets album. It’s a dry, biting look at how "total honesty" in a relationship can actually be a weapon. She sings in that low, husky alto about how maybe she didn’t actually want to know everything about her partner’s past. It’s brilliant. It’s uncomfortable. It’s Carly.
Another sleeper hit is "Why," produced by Nile Rodgers and Bernard Edwards of Chic. It’s this weird, disco-inflected anomaly from 1982 that was a massive hit in the UK but largely ignored in America. It shows a completely different side of her—funky, rhythmic, and experimental.
The Award-Winning Peak
Most people forget that Simon is one of the few artists to win an Oscar, a Golden Globe, and a Grammy for a single song. "Let the River Run" from the 1988 film Working Girl is that song. It’s an anthem. It’s huge. It sounds like New York City felt in the late 80s—ambitious, slightly frantic, and totally alive.
The "James Taylor" Era
It’s impossible to talk about her best work without mentioning the decade-long marriage to James Taylor. They were the king and queen of the singer-songwriter movement. But while Taylor’s music often felt like a warm blanket, Simon’s felt like a sharp conversation.
Their collaboration on "Mockingbird" is the famous one, but look at her album Boys in the Trees. It’s a deeply textured record that deals with the complexities of that marriage. It's sophisticated. It’s not just "folk-pop." It’s adult music for people who have been through some stuff.
The Misconception of the "Confessional" Singer
Critics in the 70s loved to label women like Carly Simon and Joni Mitchell as "confessional" singers. It was a way of dismissing their craft as if they were just reading from their diaries.
But listen to the arrangements. Look at the musicians she worked with—everyone from Mick Jagger (who did uncredited backing vocals on "You’re So Vain") to Dr. John and Bobby Keyes. This wasn’t just "girl with a guitar." It was highly produced, sophisticated pop that borrowed from jazz, folk, and rock.
How to Build the Ultimate Carly Simon Experience
If you’re trying to truly get into her catalog, don’t just hit "shuffle" on a random streaming playlist. You need a trajectory.
- Start with "That’s the Way I’ve Always Heard It Should Be". Understand the foundation of her skepticism.
- Move to the No Secrets album. This is the peak of her 70s stardom. It’s glossy but has teeth.
- Listen to "Coming Around Again". Jump forward a decade to see how her voice matured. That husky quality only got better with age.
- End with "Let the River Run". It’s the triumphant capstone to a career that refused to stay in one lane.
Carly Simon wasn't just a pop star; she was a narrator for a generation that was trying to figure out what happens after the "happily ever after." She’s raw, she’s sophisticated, and honestly, she’s a lot tougher than the "soft rock" label suggests.
To really appreciate her legacy, go find a copy of The Best of Carly Simon on vinyl. Put on "You're So Vain" and try to hear it without the baggage of the tabloid rumors. Listen to the way she holds those notes. Listen to the confidence. That’s the real best of Carly Simon.
To take your appreciation further, listen to her 1987 Greatest Hits Live album to hear how she reinvented her classics for a new era, then read her memoir Boys in the Trees to see the real stories behind the lyrics.