Janis Ian is in career-retrospective mode lately, but she’s handling it – as usual – in thoroughly modern fashion. The confessional singer/songwriter, creator of the boomer-icon hits “Society’s Child” and “At Seventeen,” has long since abandoned the major-label merry-go-ground – she’s been releasing new music on her own Rude Girl imprint for more than a decade. Nevertheless, she is getting the “Essential” treatment from Sony/Legacy with a two-disc anthology that arrived in stores and online last week. But there’s a twist: The Essential Janis Ian is essentially a reprint of a compilation titled Best of Janis Ian: The Autobiography Collection, which she self-released last year in conjunction with her critically acclaimed memoir, Society’s Child: My Autobiography.

The book begins with a clear-eyed portrait of her troubled upbringing as the child of leftists under constant FBI surveillance, and her early blossoming as a songwriter – her first song, a haunting Childe-ballad update titled “Hair of Spun Gold,” was published in the folk-music periodical Broadside when she was 12. She recorded the controversial, interracial-romance drama “Society’s Child” when she was 15; the single had to be re-released twice before it became a Top 20 hit in 1967, despite being banned by radio stations across the South, and Ian recounts a live performance that engendered so much racial hatred that she briefly feared for her life. Here she is performing the song on The Smothers Brothers Comedy Hour.

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Nearly a decade later, Ian was back on the charts with the feminist touchstone “At Seventeen,” which drove her Between the Lines album to #1 and earned her a slot on the first-ever episode of Saturday Night Live. Boomers (and post-boomers) who lost track of Ian after that missed out on some great music – her Grammy-nominated 1993 album Breaking Silence is particularly brilliant, updating her sound as she explores subjects ranging from incest (the title track) to the Holocaust (“Tattoo”) to her own longevity (“This Train Still Runs”). Ian, who had been married twice (her memoir’s description of her second husband’s abuse is punishing), began speaking openly about being a lesbian at that time – and since breaking that silence she has written columns about her personal life for The Advocate and about the music industry for Performing Songwriter and other publications. She also became one of the first artists to give away music on her website; in 2002, her prescient commentary in Performing Songwriter about illegal downloading and its positive impacts on legitimate sales got her into hot water with the RIAA and inflamed an internal industry debate that remains unresolved.

More recently, Ian entered the millennium-generation zeitgeist when Tina Fey named a key character after her in the hit 2004 film Mean Girls. Popdose tracked Ian down at her home in Nashville, where she’s taking a break from a busy touring schedule that resumes next month in the South.

We’ve all noted the continuing popularity of these similarly formatted, two-CD anthologies of major artists. But this is the first time I’ve heard of an artist’s self-released anthology being picked up by one of the conglomerates, repackaged and re-distributed. Tell me how that came about.
Well, it’s a pretty interesting comment on the state of the business. I’m in a strange position with Sony — they own part of my catalog, and I own part of it, so we really have to work together. When my book was coming out last year, I asked the folks at Sony Legacy if they wanted to do an anthology to come out with it, and they went to the muckety-mucks who said, no, there’s not enough money in it. But the book came out, and my [self-released compilation] came out, and a year later I went to them again, And this time they said, yeah, let’s do it.

Had it been difficult to secure the rights to all those old songs so you could put out the Autobiography Collection in the first place?
No, and that’s where I saw a change. They said no to releasing the album themselves, but they also said they wouldn’t hold me up. They went and got the original masters, and they helped defray the cost of remastering and distribution. And they even went to Universal [which owns the rights to “Society’s Child” and her other early-career work on the Verve label] and said, hey, you guys need to play ball on this.

That seems … unexpected.
I think that, by this point, the business has changed so much that labels have come around to the theory that happy artists will make them more money. I don’t know if Sony in general is like this, but I consistently have very good relations with the folks at Legacy.

I still find it impressive that so many of the newer compilations are truly career-spanning, and encompass work done for several different labels. You experienced the alternative yourself – there have been times when there were two or three anthologies of your work in the stores, all from different labels.
Many of us got smart about that, though, and won the rights to approve anything that gets released. You know, I own my publishing and have approval rights on [its use], so I can make sure I’m happy with the way things get done.

I would imagine there’s some satisfaction in getting the requisite Essential Janis Ian treatment from Sony –
(laughs) Yes, that’s true. I admit it.

— and I also assume you’ll get much broader distribution for the compilation now. But is the Sony release a good deal for you financially, compared to the earlier self-release?
Well, I can’t go into detail on my royalty rate, but it’s more than fair — much better than I expected. And, of course, it’ll get much wider distribution now; we’re operating at a whole different level of serious. I don’t know whether there’ll be much money in the whole thing; that’s a question for two years down the road. But, you know, it can’t help but be a good thing. It’s the same with my autobiography — it’s much better that Penguin published it, rather than “Janis Ian’s Fly-By-Night Books.”

Does your history of offering free downloads from your website, and your public criticism of the RIAA over its response to downloading, have any impact on the way you view hooking up with Sony for this release?
It’s funny, that’s for sure. At the time I was just saying things that seemed obvious to me at the time. It’s kind of like when iTunes came out, and so many folks in the industry said it would never work, it’ll kill the business. I am feeling kind of vindicated these days — not to take credit for any of it, of course. It is nice to see that some of these companies are thinking, hey, there’s another way of doing business, and starting to try to figure out what that is. Because I don’t think the old paradigm will work anymore, either for the labels or for the artists.

I caught up with that article you wrote on the subject for Performing Songwriter, and I’m astonished that you lived to tell the tale. Do you think that says more about your own status as an artist, or about the decline of the recording industry?
(laughs) It’s hardly about me, but it definitely says something about the industry. It happened unintentionally, but I think I struck a chord in that column with younger artists and people who live their lives online, and were more aware of how that whole internet culture was developing. [The column] pissed off the industry, but it seemed to hit home with a lot of people who knew things had to change. It really was a fluke — I was just looking at how downloads seemed to be affecting my own sales in a positive way, which was the opposite of what the industry was being so alarmist about.

You said the old paradigm isn’t going to come back together. Any thoughts on what the next business model ought to be?
Oh, I don’t have a clue about that! It is interesting to see the difference in the way older artists like myself have dealt with the industry’s changing fortunes, compared to the younger artists. Those of us who are over 35 know what it’s like to go through [a downturn] – you hunker down, you try to do more split bills, you try to get breaks on agent fees.

We also know that a time like this is a really good time to be cautious, and polite, because you never know when you’re gonna run into somebody again, and if you do something for somebody today maybe they’ll return the favor later. I guess that may be part of why things went so smoothly with Sony Legacy in getting this album together. Whether the other record companies have learned any of these lessons, I don’t know. You know, they’re like any of the established industries — like the car industry – and it’s hard for them to change because they only know what worked in the past, not how to make something else work in the future.

I’ve been working my way through your memoir, and I was stuck particularly by the fact that you don’t engage in a lot of self-analysis about everything that’s happened to you. It made me wonder how you approached the memoir – whether you thought, “Finally I get to tell all these stories!” or if you wondered whether telling them might stifle your songwriting.
Actually, neither of those were true. I just thought, what do I have to talk about that would interest me if I were reading it? My main concern was that it not be self-serving or boring. That’s really it. I’d read a number of other memoirs, and they taught me a lot of things that I would want to do – or not to do. But you’re right, I really didn’t get into a lot of self-analysis in the book; I just wanted to lay out the events and let people evaluate it for themselves. I figured I’ve done enough analysis already!

I was only 9 years old when “At Seventeen” came out, so it took me a while to catch up with the themes you were exploring then —
I would hope so!

— but I have to tell you that Breaking Silence was probably one of the three or four albums I played most often the year it was released. I remember the publicity back then about you coming out, and I remember wondering why a confessional songwriter such as yourself would wait as long as you did to make that fact public.
Well, it was never really a secret — I always lived with women — but I think everybody got confused because I married a man! I never thought it was a big deal, honestly. I’m not happy being seen as a poster child for anything. I’d rather just think about writing and making records, to be honest.

But it was pretty much as I described it in the book — I decided to publicize my sexuality because of the statistics that were coming out about teenage suicide at that time [a study had shown that as many as three in 10 suicides among teenagers happened because a teen worried he or she was gay]. I decided I needed to come out in order to give kids … not necessarily a role model, but one more example of someone who had been through what they were going through. I thought it was unfortunate that the whole thing was discussed so much in the press at that time, in the way that it was.

I happened to find a copy of Who Really Cares [a slim volume of Ian’s poetry, published in 1969] at the public library. What do you think of those poems today?
Oh, that’s great that it’s still out there. Why?

I had a conversation with Paul Simon, back after Graceland came out, and he was dismissive of practically all his older work. I found myself defending Simon & Garfunkel songs to the man who wrote them.
Well, I guess that’s natural for him to be more interested in what he’s doing at the time. But you can’t let his judgments affect how you feel about the songs, because then you’re saying that the artist is the work. There has to be some distance, or else the work can’t stand on its own.

That’s an interesting way to look at it.
I don’t think about [the poetry collection] much anymore, but I certainly don’t think less of it than I used to. The cool stuff for me is finding out that Johnny Cash had a copy of it in his library.

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