Simon, of course, went on to release a slew of Hot 100 top 10 hits (including the chart-topping classic "You're So Vain" in 1972) and critically acclaimed albums, furthering her place as one of the leading voices of the ‘70s, and a guiding light for similarly candid yet heart-smashing artists to come: Tori Amos, Natalie Maines and Taylor Swift, the last of whom even brought Simon out for a live performance of her signature No. 1 hit in 2013. Flash forward to 2021, and there's now Olivia Rodrigo’s world-beating smash, “driver’s license,” where much of the song’s mystique is steeped in the same true-life intrigue as Simon’s “Vain” — who the heck are they singing about and why does digging into that real-world drama make the song so much more rewarding?
Simon, 75, is currently preparing to release a remastered version of her famed 1995 concert filmed inside New York’s Grand Central Station, saying that the revamped footage is coming soon. Last week, Billboard caught up with the icon by phone from her home in Martha’s Vineyard, to revisit her momentous self-titled debut, just how it was forged and many of the career highlights that passed by since, like clouds in her coffee.
Let’s flash back to 1970-71, when you were making your debut album. What was going on in your life at the time?
The previous two years I was writing material, still not knowing if I was going to be accepted by a record company. So, I was just working and writing, and I was doing some jingle singing for my uncle, who had a jingle company. He was getting me in for $5 to do a jingle. I was working for another company too, called Harmony Dell Associates, and I've got some pretty funny examples of the jingles that I was doing. One was Noxzema and another was O-Cedar, the mop company. And a bank in New England.
So, there were about 10 commercials I did, and then I did [the music for] a television show for NBC called Who Killed Lake Erie, and for that I wrote the melody that turned out to be “That's The Way I've Always Heard It Should Be.” I had never taken piano lessons, and I just learned guitar from a couple of friends of mine and my sister, and so I was writing, really, as an amateur.
Then the summer of '69, I met [future songwriting collaborator] Jake Brackman up at Indian Hill Camp. We were both counselors, and he was the literature counselor and I was the music counselor. That fall we started kind of seeing each other a bit. We both lived in Murray Hill [Manhattan], and I moved into Murray Hill in 1969, and I had an upright piano there, which my aunt had given me, called a Tonk. I started writing songs on the piano, and I wrote about eight songs between 1969 and 1970. Actually, more than that, because I wrote a lot of lyrics, which I didn't end up using.
How did “That’s The Way I’ve Always Heard It Should Be” end up as the single?
“That's The Way I've Always Heard It Should Be,” is an example of how, if I wrote the melody first, it was very hard for me to get the lyrics after I'd written the melody. So, Jake and I were sitting around one night and I said, “What about if you tried to write some lyrics?" And he demurred, even though he was already the writer for Talk of the Town, The New Yorker, and Newsweek. He was considered a great young writer of his generation.
So he wrote the words to “That's The Way I've Always Heard It Should Be” -- or most of the verses -- and I loved them right away. He did such a great job, and we honed it, and then that's the song that ended up being the single, because it was so unusual. People said that they'd never heard a song like that. It was more of an art song than anything else.
I'm not sure who I was copying, but I certainly was copying a lot of the singers and writers. Well, there weren't that many, but I had been listening to a lot of the [early 20th Century] French composers known as Les Six. I listened especially to Poulenc and I was just so inspired by his clarinet concerto and his flute concerto. I'm sure I borrowed a lot of the melodies that Poulenc wrote. I was really influenced by so many different kinds of music, because my father was a classical player of the piano, as well as a publisher, of course, and my sister, Joey, studied studied opera, and then [my other sister] Lucy and I had been doing folk music together, and my mother sang show tunes, and my uncles were jazz musicians.
Wow, so you were really all over the place.
All over the place. I mean, I wanted to be a jazz singer. I wanted to be like Annie Ross, from [jazz vocal trio] Lambert, Hendricks & Ross, and so when I made my first demo tape I sent it to [producer and Hit Factory founder] Jerry Ragovoy, he said, "You know, I like it, but I don't know who you are. I don't know who to market you as." So, then I got a manager, and he took it to Jac Holzman and Clive Davis. Actually, he took it to Clive Davis first, who was at Columbia, and supposedly -- I don't believe this, but -- supposedly Clive threw my tape across the room and said, "What do I want with... " I won't say what he wouldn't want with it, but it was something a little bit not nice.
So, it was taken then to Jac Holzman at Elektra, and apparently everybody turned it down. Everybody at Elektra voted it no, because he had these roundtable Tuesday sessions at lunch, and all the heads of the divisions were there, and they all voted it down. I think he played only “That's The Way I've Always Heard It Should Be” and one other song. But Jac had a veto power, and so Jac vetoed their vote and said, "There's something about her that's different and interesting, and I vote yes."
Flashing forward about a year, to 1972, you prove everyone wrong and win the Grammy Award for Best New Artist. What do you recall from that night?
Well, I was with James [Taylor] at that time... we had just gotten home from Japan, where James was on tour, and we landed in San Francisco the day of the Grammys [James Taylor was up for Best Male Pop Vocal Performance]. And we were both too afraid to be there -- I was probably afraid that I wouldn’t win and be sad, I don't know what James's fears were -- but we decided not to go to the Grammys, and just to drive slowly and linger on our trip down Route 1, on the coast of San Francisco to L.A.
So, we drove down and it got to be very late and foggy at about 3 o'clock in the morning, because we intended to get there after the Grammys, and we would hear the bad news when we got to L.A. But instead it was so fogged in at Big Sur that we decided to get off the highway and find an inn. We found the Big Sur Lodge and we drove into it, we checked in, we got to the cabin, and there was a telegram on the door of our room saying, "Dear James and Carly, you both won." Jac Holzman had sent a telegram to every single possibility of a place that we might stay along that route.
Let’s jump ahead again, to 1977, when you released “Nobody Does It Better” for the film The Spy Who Loved Me. What was the thrill like, to be associated with a James Bond movie? And any thoughts on some of the latest Bond themes?
I heard the Adele and the Sam Smith ones, and I thought they were both good. I didn't like them as well as “Nobody Does It Better” -- but I think “Nobody Does It Better” was the perfect song and I was the perfect artist for it at the time. When I first auditioned the song, it was just before Christmas and I was expecting my tax lawyer to come over for some reason to my apartment. I was very pregnant with [my son] Ben, and so I had a 1 o'clock appointment with my tax lawyer, but I had somehow made an appointment that conflicted with the tax appointment guy so the doorbell rang at one o'clock, and this man came in. He was obviously the tax lawyer. He had horn-rimmed glasses and a work suit.
I said, "Why don't you wait in the living room?" So, he waited in the living room and I asked him if he'd like a cup of tea, and he said, "Yes, I would very much." So, he went into the living room and I went into the kitchen and put on the kettle, and after about a minute I heard [hums melody] on the piano. It was [songwriter] Marvin Hamlisch looking like a tax lawyer! He played the song for me and it was a natural right away. It just fit my voice. It was quite wonderful.
Back to 2021: Have you heard “driver’s license” by Olivia Rodrigo? The current No. 1 song on the Hot 100?
I ask because so much has been discussed about who Olivia is singing about, akin to “You’re So Vain.” Do you have any other favorites of these kind of mystery-subject, real-life-intrigue romantic diss songs of recent decades?
I think you only get one of those [laughs], and for Olivia to be 17 and to have people wonder who she's singing about, she's very precocious.
Throughout your career, it seems like you've always put the art and songwriting first, above all else. In the early years, did you ever need to fight or refuse to compromise to release the music you wanted?
I did it with a soft touch, I think. I think the biggest departure that I had was when I was with Warner Brothers [in 1980] and I had just had a big record with “Jesse.” I then wanted to do an album of torch songs, because James and I had just broken up and they seemed to suit my mood so well. Plus, I'd always had that part of my repertoire, which I revered, because those songs are songs that I grew up with, and shows and with jazz singers.
So, I felt comfortable singing them and I wanted to record the album Torch. At the time, [Warner Bros. executive] Mo Ostin decided not to promote it, which was very disappointing to me, and he since apologized to me and said that was one of the biggest mistakes he's made in his career, not promoting it.
Another throughline in your career has been intense stagefright. Yet you’ve still managed to put on many memorable performances over the years. Any tips or tricks to share for, say, nervous public speakers?
Well, one thing that I made a habit of the last 10 years of performing was that my band would have to spank me before I went on stage. And they'd spank me so loud and so hard that I'd be stinging by the time I went on stage, and sometimes the physical pain of being spanked overcame my heart fluttering and my panic.
Literally spanked, on your backside?
Literally. They all lined up and spanked me. One time I was singing a happy birthday concert to Bill Clinton. He and Hillary were sitting in the front row, and Smokey Robinson had just been on. The curtains closed, there was a whole orchestra behind me. So, my band came on stage and stood in front of the orchestra and my band lined up to spank me, and the curtains opened early, so the whole audience got to see me being spanked, at least the last two spankers.
I will definitely have to try this.
Do it, it really works, and you can double it up with a rubber band around your wrist. But the spank is more unusual, it gets people laughing.