Growing up [in Winnetka, Illinois, near Chicago], I was a happy child and I would say an unhappy teenager. I felt frustrated about paying into a system that I didn’t think was going to serve me. Do good, be good, get good grades. I could already tell that it was going to pay out for the teachers and the parents, but wasn’t going to work for me. Getting into college was just as hard back then and the pressure … you saw your friends everywhere, unhappy or with eating disorders or suicidal. It seemed like no one cared. They just wanted to keep pushing you forward, keep making sure that you were going to represent your parents and the area, blah blah. It was a conservative environment where people didn’t dress to stand out, so for the longest time I had two wardrobes. If I wore what I wore in the city to the country club, someone would rush out with a sweater to put over my shoulders because bare shoulders were an outrage.
I listened to REM’s Murmur and Reckoning albums over and over again, partly because I couldn’t understand what he [Michael Stipe] was singing. They were so painterly. They felt like an abstract, conceptual take on Americana. We’d all had the template of classic rock seared into our brains, and then REM came along and just like tossed it out of the way, to the point that you couldn’t even hear the words.
In my early teens I had braces and wore glasses, then suddenly at the start of freshman year I didn’t need the braces any more and I got contact lenses and a haircut. The power of that transformation and the attention I got from people afterwards made such a big impression on me because I felt, “Huh. I didn’t do anything …” I was so obsessed with the  movie The Hunger, I must have watched it 60 times. I imagined being like [whispers] “Yes, can I help you?” in my ancient pile. Catherine Deneuve and Susan Sarandon were just incredible. Totally gripping. That’s who I wanted to be when I grew up – a 6,000-year-old vampire with so much style. In the 80s there was an obsession with beauty and superficiality, a smooth gloss which probably came from cocaine and permeated all culture, but when I saw it portrayed as this sickening bloodlust and erotica, I just thought it was perfect. The daytime 80s was all people wearing trainers with their dresses and women in business suits, but I gravitated towards the night-time 80s, this magic time of The Hunger and Labyrinth and metaphysical, spiritual children’s movies. My conservative upbringing meant I wasn’t allowed to dress the part, but internally I was a goth.
We had to pick a literary icon for a 20-page paper. I chose Ernest Hemingway’s  novel The Old Man and the Sea and was told by my teacher that it was a children’s book and that it wasn’t long enough or intense enough to warrant this kind of paper. I knew that she was wrong and silly and stupid, so I thought: “Hemingway is too short? Fuck you. I’ll go even shorter.” I picked EE Cummings. I didn’t know anything about his work apart from that it was so minimal. Then researching that paper I just fell in love with him. I became obsessed with the musicality of his wordplay, the way he would break words in half and move you through the rhythms of speaking this poetry. Playfulness with words. To this day he’s a powerful influence on how I write my songs.
The Grateful Dead
For some reason the Grateful Dead were considered the acceptable childhood rebellion. Going to see the Dead was the only place my parents would let me go overnight. Like, you could be hippy, on the weekends, in the summer. My friends could all pile in the car, go up to Alpine Valley in Wisconsin, watch the Dead and spend the night in tents. I must have seen them about eight times. It wasn’t just the shows that were magical experiences, or the fantastic songwriting. It was the show behind the show: the Deadheads following and the camaraderie and loyalty, and this whole travelling village where people would trade food if you’d sing a song, and sell acid and weed. I think I first took mushrooms at a Dead show. I was 16, in my sophomore year of high school and looking for the path of least resistance to freedom and adulthood.
I was lucky that my generation had all these fundamental shifts in music: Walkmans, samplers, and later on the internet. MTV was one of those things. Suddenly, you could see the band that were on the radio. You could dress like them, obsess about them, fall in love with them. It was such a profound shift. It felt like music was taking over the TV, like television was boring and our heroes were coming to destroy it. It hit just when I started going to high school and it just spread like an absolute wildfire. I became obsessed with music videos and had a different favourite depending on the hour I was listening: Siouxsie and the Banshees, Tom Petty, hip-hop, the Replacements’ parody video [Bastards Of Young] where they’re just filming their own speaker. Every band had something to say and they showed it visually. It felt like the revolution was here.
Back then I had zero plans to work in music. I wanted to be a visual artist and was very ambitious about it. My parents would have probably liked me to become a wife; educated and interesting, but a wife. When I was 16 I started dressing like Madonna. All the girls did. It was her first record – Madonna  – and we were marvelling at this cool chick who wore all these layers of clothing and jewellery, and had crimped hair and little skirts and little boots. Nobody had any clue that she would become such a phenomenon. To us she was just a dancer from New York. We’d go downtown, and where could you go when you had no money? To museums or walk the park or hang out in coffee shops. Suddenly everyone I thought was cool looked like her. We don’t have that any more: someone who comes in and changes fashion and everything, right across the board.
A year or so later I stopped going to school for a year. They tried to find me but I was downtown, taking pictures of cemeteries. If you keep certain creative people in too tight a box, they blow up the box. I didn’t get into any of the colleges that I should have gotten into but it started a chain of events that led to my first record. I don’t look back and think what a great person I was. I was whiny and angry and felt sorry for myself, but I don’t think the teenage me was an asshole. I’m proud of her for taking those first steps.
• Soberish, Liz Phair’s first album in 11 years, is released on 4 June via Chrysalis