I have, quite accidentally, wandered into writing my autobiography. Eight years ago, when I was turning 35 and dealing with some huge life changes, I made a playlist of 70 songs – two for each year I’d been alive – that added up to a soundtrack of my life, and I captioned each with a brief story. Because 2014 was a very weird time for sharing things on the internet, I put the annotated tracklist on Pastebin, uploaded the playlist to 8Tracks, and almost lost the whole thing. Four years later, when I was about to turn 39, I managed to move the project to The Finer Sports and create playlists on YouTube and Spotify, which so far have proved less ephemeral.
Now, I’m 43, and I have new stories and songs. I’ve been updating the Spotify playlist throughout the four years since my last update, keeping a record of the songs that have captured my imagination and narrated my life, musing about which stories might accompany them. This project feels as meaningful now as it did the first time.
So here we go. The first 78 songs on the list are the same as they were in the 2018 version of this post, although I’ve updated any broken YouTube links (current YouTube playlist here). I’ve also left the stories alone, save for a touch of proofreading and some pronoun updates. At the end, I added eight new songs with accompanying stories that I hope will go some of the way toward summing up who I’ve become over the past four years, in the context of the people I’ve been throughout my life.
Hall & Oates – Sara Smile
When I was three, I used to ride my rocking horse while listening to pop music. Like, “The Rocking-Horse Winner” levels of fervent rocking, straining the springs as if I could free the horse from its frame.
The Four Tops – Bernadette
Names I gave to my pet guinea pigs as a kid: Butterball, Spike, Buzzy, Ms. Peanut, and Bernie the Klingon.
Cyndi Lauper – Time After Time
Family vacation on the beach in Ohio, lying in the sand listening to my cassette of She’s So Unusual on my bright yellow waterproof Walkman.
Aretha Franklin – A Change Is Gonna Come
I sucked my thumb until I was nine. As a reward for quitting, my parents let me get my ears pierced.
The Cure – Friday I’m in Love
My grandmother – not the Shakespeare one, but my dad’s mother – made me and my brother any Halloween costume we wanted. Therefore, I was a toasted marshmallow one year in grade school. She stretched white fabric over a wire frame and splatter painted it with brown and black puff paint.
Cheap Trick – Surrender
I got the chicken pox for my tenth birthday. I read 1984, Lord of the Flies, and several Edward Albee plays that I’d pulled from my parents’ bookshelf. After I’d recovered, I gave a book report that confused the heck out of my fourth grade teacher.
The Drifters – Under the Boardwalk
For my Freestyle 2 figure skating test, my coach let me choose any song I wanted. So a song about getting busy on the beach makes me think of the ice.
Carole King – Will You Still Love Me Tomorrow?
In the grade school pecking order, I fell somewhere in the middle. All of the top-caste popular girls were nice to me, and two were genuinely my friends. And at Hebrew school and the ice rink, I was one of the elites. I was a buck-toothed bookworm with thick glasses and gender issues, but somehow, I had enough social finesse to get by. I sometimes feel like I lack geek cred as a result of not being a childhood social outcast.
Sam Cooke – Bring It on Home to Me
My junior high school had a program that would have let me start taking high school math in seventh grade. The catch was, if I participated, I couldn’t take Spanish or band, my two favorite subjects, and might not have had time for my early morning skating practices either. I told my mom I didn’t want to do it, and to her credit, she said okay. This inspired two other kids in my grade, of only about seven who had qualified, to turn it down. The school didn’t know what to do with this tiny insurrection.
The Who – I Can See for Miles
My grandmother – not the one with the Halloween costumes, but my mom’s mother – started taking me to Shakespeare plays and to the opera when I was about 11. Within a year, I was the only one she would take to Shakespeare, because she claimed I was the only one she could have an interesting discussion with about it afterward.
The Beatles – If I Fell
In seventh grade, I had my first boyfriend and kiss. We started going out because we both liked The Hitchhiker’s Guide to the Galaxy. It lasted a month, which feels like forever when you’re twelve.
10,000 Maniacs – These Are Days
When I was nine, I begged to redecorate my bedroom in red, black, and white. I got pink and powder blue. At twelve, I covered one wall with Michael Jordan posters and the other with photocopies of Far Side cartoons.
Bob Dylan – Don’t Think Twice, It’s All Right
The assigned Haftarah portion for my Bat Mitzvah date compared the Jewish people to an unfaithful wife. I refused to read it on the bimah because it was so sexist. I got to read the famous passage from Ecclesiastes instead: “To everything there is a season, and a time for every purpose under heaven.”
Maná – Rayando el sol
My parents tried sending me to Girl Scout camp and horseback riding camp, but the only overnight summer camp I enjoyed was foreign language immersion camp. I emerged fluent in Spanish.
Talking Heads – And She Was
We were reading Julius Caesar in English class my freshman year of high school, and the teacher wouldn’t stop insisting that Marc Antony was the hero of the play. She did a great job of putting an anti-authoritarian teenager on Team Cassius for life.
Matthew Sweet – We’re the Same
My first assignment as a staff writer on my high school literary magazine was a history of film adaptations of Dracula. Between that and the Julius Caesar standoff, I was ready for graduate school in English by my fifteenth birthday.
Janis Joplin – Me and Bobby McGee
The driving instructor taught me to parallel park on a street with the same name as my last name, but spelled differently. Even now, when I see a stop sign, I hear her in my head crooning, “Compleeeeeeete STOP.”
R.E.M. – Driver 8
Q: How many teenagers fit in a 1990 Ford Taurus bound for Lakeview on a Saturday night?
A: Eleven.
They Might Be Giants – Shoehorn with Teeth
I wrote a high school English paper about The Adventures of Huckleberry Finn entitled “Take This Great American Novel and Shove It.” I got an A.
Patti Smith – Ghost Dance
The most trouble I ever got into in high school was for blowing my curfew to stay late at a Star Trek convention.
Leonard Cohen – Take This Waltz
The buses didn’t leave my high school until almost an hour after the final class period ended. I spent the in-between time reading Angels in America, The Children’s Hour, and Poeta en Nueva York. I came out of the closet to books first.
Fiona Apple – Sleep to Dream
We were allowed to take dance classes for gym credit. Of all my teachers senior year, my dance teacher was the only one who understood why I chose the college I did.
Pavement – Cut Your Hair
My high school’s Scholastic Bowl team was the scourge of the state, partially because we paired our buzzers with representative Beanie Babies and wrote our favorite Dr. Seuss characters on our name cards, but mostly because two guys on the team could take derivatives in their heads, and I could buzz in with “Ralph Ellison” before the moderator could finish saying “Tuskegee University.”
Crowded House – Fall at Your Feet
The Star Trek Club reserved a classroom at the Winter Carnival. Whatever the original plans were, they fell through. My friend and I said we’d come up with something. What we came up with was a prank booth, a riff on Ingmar Bergman and Monty Python. Not many people came in. In between sporadic visitors, we made out. He was wearing grease paint, and it smeared all over my face.
The Velvet Underground and Nico – Heroin
Standing outside the Starbucks in Glencoe, Illinois, we discovered that among the three of us, we knew all the words to this song.
Björk – Hyperballad
The summer between high school and college, I played Hermia and all of the fairies in an eight-actor production of A Midsummer Night’s Dream.
Elvis Costello & The Attractions – Radio Radio
I took a course in internet systems administration during my freshman year of college. I had the passcode to a secret computer lab across from the art gallery so I could practice hand-coding HTML and executing UNIX commands, and also sit until all hours of night reading Buffy the Vampire Slayer fan fiction.
Ani DiFranco – Both Hands
I went to the Mobil station with two girls who were also named Sarah. We flashed our boobs so the guy wouldn’t card us when we bought wine coolers. My dorm was next to the college day care center, and the three of us got drunk in the playhouse on the playground.
Richard & Linda Thompson – Wall of Death
At Cedar Point with my brother and cousins, we rode every roller coaster in the park in two days. We even scammed our way onto the kiddie coaster.
Iggy Pop – The Passenger
A friend and I took the train from New York to Washington, DC, for October Study Days, and stayed at their dad’s house. The cat who didn’t like anyone slept in my bed every night I was there; her name was Kerouac. My friend and I got in loud fights about Hamlet and queer identity, and they lent me their trades of The Sandman.
Radiohead – Karma Police
I went to Baltimore with my mom for spring break. We trespassed on the deserted sets of Homicide: Life on the Street and found a discarded production memo on the floor. Then, we went to the aquarium and watched three IMAX movies in a row.
Lisa Germano – The Dresses Song
I went to the queer youth conference with the girl I was crushing on, thinking for the first time, maybe I can tell her, and she’ll like me back. Another girl at the conference – too pushy, too much the wrong kind of butch – wouldn’t stop hitting on me, wouldn’t take the hint. By the end of the night, I had a girlfriend, the one I wanted.
Robyn Hitchcock – Airscape
The last Shakespeare play I saw with my grandmother before she died was Henry IV Part 2, which was a little too on the nose.
Fountains of Wayne – Survival Car
My brother visited me in New York during one of the hottest summers on record. The A/C was busted at the Fountains of Wayne show I took him to in Union Square. “Please don’t rock me tonight, it’s too fucking hot,” they sang, but also, “Riding on the path we made, and now we’re here.”
Elliott Smith – Say Yes
I walked home from a girl’s flat the morning after, wearing a pair of pajama bottoms she’d lent me. They were too long, and I had to bunch them up in both hands to keep them from dragging along the damp pavement. The guy who lived across the hall from me had just found Jesus, and he was praying for me.
Guster – Either Way
In Bruges, we got drunk on Hoegaarden, bought handmade chocolates, and got so lost we almost missed the train back to Brussels.
Warren Zevon – Boom Boom Mancini
My friends dragged me to the Renaissance Faire. They told me I had to wear a costume, so I dressed as Hob Gadling from The Sandman: jeans, black t-shirt, minimal patience for historical inaccuracy. A woman read my tarot cards and told me I was psychic, too.
Aimee Mann – Nightmare Girl
To stave off homesickness when I lived in Japan, I rented VHS tapes of E.R. episodes, two at a time, with Japanese subtitles.
Hitomi Yaida – Ring My Bell
The woman at the okonomiyaki shop loved it when we foreigners came in. The process was like a dance: cabbage on top of pancake batter flipped onto frying noodles, then flipped back onto a layer of egg.
The Pixies – Where Is My Mind?
I had a presumed one-night stand with a Navy girl at a lesbian retreat in the mountains outside Nagano. I wrote my phone number on a strip of duct tape that she stuck to her shirt. She kept calling back until I fell in love.
Dan Bern – Jerusalem
To take my GREs, I had to fly to Sapporo and navigate public transportation to the international school. When we arrived, we were told that the exams had been shipped to the wrong location, and we would have to return in two weeks. So I got to see Sapporo twice.
Joe Jackson – Real Men
My partner lived with me for my last few months in Japan, after their Navy tour ended. My neighbors saw them shoveling snow and assumed they were a boy.
OutKast – Hey Ya
“Hey Ya” placed in the top three in WXRT’s song of the year poll for 2003. I was at work, listening to the radio, the first and only time that radio station would ever play it (or so the DJ said). On other days at the same job, WXRT would inform me of the deaths of Elliott Smith and Warren Zevon.
Rachael Yamagata – Worn Me Down
We were only supposed to get the one kitten, the black and white one. We saw the calico and knew she was ours. These cats outlasted six apartments, two long-term relationships (mine), three serious health scares (theirs, one involving the ingestion of a dime), and the countless indignities of being loved by a human.
Catie Curtis – Bicycle Named Heaven
My partner and I would drive up to Northampton, MA, for folk music, a decent meal, and a place where we could walk around holding hands without feeling like freaks. For Catie Curtis, we got to the Iron Horse early. “Bicycle Named Heaven!” we shouted in unison, and she played it for us. Just for us.
The New Pornographers – The Bleeding Heart Show
We had been warned about each other. Both of our relationships were failing. We ran around naked in our friend’s tiny backyard. It didn’t count as cheating because our partners were right there, and because he was a guy.
Kanye West – Jesus Walks
My graduate seminar in early modern religious poetry was at 9:00 AM. During the mid-class break, impassioned disagreement would break out about the previous night’s episode of Project Runway. I gave a class presentation on the influence of John Donne’s poetry on Kanye West. It wasn’t the class I thought I’d signed up for.
Christine Fellows – Veda’s Waltz
My partner and I flew out to California for a convention because the entire Firefly cast was scheduled to be there, except for Gina Torres. Joss Whedon made a surprise appearance. Morena Baccarin and I chatted about Shakespeare when the autograph line backed up. Nobody knew who Christina Hendricks was yet, so she was sitting in a near-deserted side room, and we had a twenty-minute conversation.
Thao Nguyen – We
I asked the director of graduate studies when I was going to hear whether I’d be re-accepted into the Ph.D. program. She handed me an envelope with my MA exam results and whispered, “You have nothing to worry about.”
Wolf Parade – Shine a Light
Liquor stores in Connecticut used to be closed on national holidays. On Memorial Day, I piled in a car with three big dudes, and we crossed the border into Massachusetts for beer. We bought Diet Coke and Mentos, too, and made a geyser in my friend’s driveway while his neighbors cheered. That’s what four master’s degrees and a full tank of gas will get you.
Ben Folds – Landed (With Strings)
I have had three long-term relationships in my adult life. I ended both of the first two during episodes of So You Think You Can Dance.
Thea Gilmore – Avalanche
I watched four adaptations of Othello in one weekend afternoon with a friend who was realizing she hated grad school. We invented the Desdemona: raspberry vodka, orange liqueur, and pomegranate juice, shaken and served straight up in a martini glass.
Kelly Clarkson – Since U Been Gone
My ex had until December 31 to get her stuff out of my apartment. She took all the lamps and my complete set of Transmetropolitan trades but left her desk and a ton of her DVDs. The desk lasted until I moved out on my next girlfriend, six and a half years later. I still have the DVDs.
Rogue Wave – Bird on a Wire
I lived for four years in a converted factory in New Haven, CT. The leasing agent mentioned corsets having been made there, but the neighbors told me there had been coffins, too. We all agreed there was a ghost in the freight elevator.
Basia Bulat – In the Night
The first time I got paid for my writing, I spent it on shoes and a dress. And bills.
The Buzzcocks – Ever Fallen in Love (With Someone You Shouldn’t’ve)
Online dating, I met a girl named Sarah. I don’t remember where she lived – somewhere Mid-Atlantic, I think – and she took the train up to Connecticut to meet me. She had lupus, and the medication had made her gain weight. I couldn’t convince her that I thought she was beautiful.
Tegan & Sara – The Con
The New Haven lesbian kickball league only lasted one game. Or, possibly, it continued in secret, but I was kicked out because I brushed it off when that one woman tried to seduce me by “teaching” me to play pool.
Brandi Carlile – The Story
I met the second great love of my life at a wedding in Rhode Island. We danced to “The Time Warp” and talked about our love for Johnny Weir. A year later, she asked me why we’d never kissed.
Frightened Rabbit – Head Rolls Off
The man who should have been my dissertation adviser literally wrote the book on gay pirates. He died of cancer during my last year of course work. His yahrzeit falls during the same week as my grandmother’s. He was Episcopalian, and I’m pretty much an atheist (as was my grandmother), but every summer I say kaddish for both him and Granny.
Lady Gaga – Bad Romance
My girlfriend and I loved a lot of the same things – raw oysters, Broadway musicals, figure skaters in sparkly onesies – but she hated my taste in music. I’d tease her for listening to mainstream crap, and she’d berate me for listening to pretentious droning. We agreed on Lady Gaga, though.
The National – Runaway
Every time I graded papers in the coffee shop on Orange Street, I asked the barista what song this was. Every time, it was The National.
The Weakerthans – Plea from a Cat Named Virtute
I called the university health center to schedule an appointment for mental health services. A panic attack immediately followed the phone call. The cat hopped into the bed. “I know you’re strong,” she seemed to say.
TV on the Radio – Wolf Like Me
The photo montage for my brother’s wedding wouldn’t play correctly. It caused an awkward silence at the rehearsal dinner. As the member of the wedding party with the most computer knowledge, I was charged with making it work. I got the video to play, but the audio was gone. The band put this song on to accompany it. It went better than whatever my brother and sister-in-law had originally picked.
Bloc Party – Signs
For four years, a friend and I carpooled from New Haven to UConn’s main campus to a soundtrack of NPR and “Total Eclipse of the Heart.” We both wrote half our dissertations at 70 miles per hour on I-91.
The Mountain Goats – Up the Wolves
Hurricane Sandy knocked out our power and hot water for ten days. We lasted two nights in our dark, cold apartment before my girlfriend’s parents insisted that we come stay with them. They were nothing but gracious and warm the entire time, but my girlfriend was on edge, convinced that her Republican, Italian family would never accept her same-sex relationship. In reality, I’m pretty sure her parents liked me better than any of her siblings’ spouses.
Wye Oak – Civilian
I bombed the third interview for a community college job that would have saved my relationship but squashed my career dreams. In retrospect, they could smell that I didn’t wholly want it, that she couldn’t keep me.
Donna Summer – I Feel Love
The night Donna Summer died, my girlfriend and I stayed at the gay cabaret until last call and drove home while the sun rose. Or maybe that was Whitney Houston, and Donna Summer was the time I brought my parents.
Shearwater – Animal Life
On my first night out as a Doctor of Philosophy, Shearwater played an old R.E.M. song during their encore. I had accomplished all of my life goals.
Regina Spektor – How
I came home for Thanksgiving alone. My girlfriend wanted to spend Thanksgiving with her own family. On the plane, I listened to this song and realized I had to leave her. I stuck it out for six months afterward, but the song was right.
Canasta – Slow Down Chicago
Two weeks after I left my girlfriend for good, I got a college faculty job in the hometown I thought I’d never move back to. I flew to Chicago with 36 hours to find an apartment and sign a lease. The third place I visited had a dishwasher, central HVAC, and cheery blue walls in the living room. I shocked the leasing agent when I told him to take me to the office to sign paperwork, because I’d come home.
Sia – Chandelier
At my cousin’s wedding, a falling-down drunk wedding crasher tried to hook up with me on my way to the bathroom. After I’d turned him down and regained my composure, I joined an army of cousins – all of us too old for this behavior – in crashing the other wedding in the same hotel, which was a same-sex marriage with a drag queen DJ. We even took a family picture in the photo booth.
Foals – Mountain at My Gates
I locked myself in my office to grade papers and blasted indie rock that I knew none of my co-workers could stand, because I couldn’t deal with any of them anymore, no matter how much I loved my students. I’d spent a decade of my life training for this, and now I had to let it go.
Kishi Bashi – Once Upon a Lucid Dream (In Afrikaans)
I almost got a press pass to the 2016 World Figure Skating Championships. The ISU notified me a week before the event that there weren’t enough slots for me and my little blog. I already had my flight and Air BnB booked, so I found a last-minute all-event ticket in the front row of the nosebleed seats. I made friends with a guy in my row who had done basically the same thing, and we spent the week drinking beer and yelling for the skaters like real sports fans. My crowning accomplishment was getting the guy at the concession stand to wear a Red Lipstick For Ashley button during the ladies’ free skate.
Stevie Wonder – Sir Duke
As I held my niece for the first time, I marveled at how lucky I was that I’d know this amazing, tiny person for the rest of my life.
John Grant feat. Tracey Thorn – Disappointing
My heart thawed for a food writer. Our relationship was fueled by restaurant one-upmanship. He’d lure me to Chinatown with promises of Sichuan chili chicken, and I’d drag him out to Albany Park for Filipino fried rice and pork belly. He won the game when he took me as his plus one to a food festival on a rooftop downtown and introduced me to all the chefs he knew personally. The romance could only go downhill from there.
Against Me! – Black Me Out
I went to the Chicago Women’s March with my mom, my sister-in-law, and my best friend. There were about five times as many protesters as the city had planned for, so the march became a standing demonstration, a peaceful mob. After the speeches ended, the police tried to kettle us at Jackson Street, but the barricades were no match for thousands of fired-up Chicagoans, flowing like melting snow toward Michigan Avenue.
Benjamin Clementine – Nemesis
The seller of my dream home accepted my offer at 11:00 on a Saturday night, after I’d been stood up for a date.
Ezra Furman – Driving Down to L.A.
I couldn’t bear to go to my grandfather’s funeral alone, so my entire extended family and all my parents’ friends met my new girlfriend in the receiving line.
Vampire Weekend – Harmony Hall
My father didn’t like what I’d chosen for my new middle name, so he got to rename me. If I’d been assigned male in the first place, it would have been Daniel, for his grandfather. So I’m Sarah Daniel, as perhaps I’ve been all along.
Starflyer 59 – Young in My Head
When we got to Milwaukee for the Weird Al concert, our hotel booking had disappeared. For baseball reasons, there were no rooms available anywhere. The woman standing next to us at the counter was in the midst of canceling her room. Sometimes, instead of questioning fortune, you just enjoy your weekend.
The Decemberists – Make You Better
A few weeks before everything shut down for the pandemic, I got really sick with the flu, or something like it. When I called the doctor, I was told to stay home and isolate, as I would be putting myself and everyone around me at higher risk by leaving to get a test. It was a case of Schrödinger’s COVID.
Miike Snow – Genghis Khan
The ring wasn’t ready on the weekend when I was planning to ask my girlfriend to marry me, so I proposed to her with a Beauty and the Beast tiara that I’d snuck out to buy from the Disney Store.
Parliament – Agony of Defeet
I volunteered for jail support at the Cook County Jail, driving people home (or wherever they wanted to go) after they were released. I’d made a playlist for the car: old-school hip hop, vintage R&B, a smattering of disco. But nobody was being let out that night, so we linked my phone to another volunteer’s Bluetooth speaker and had a dance party for prison abolition.
Elle King – The Let Go
My first pandemic year was measured in the lives of cats. Callie died suddenly of heart failure in October, fading in my lap while I watched the Skate America men’s free skate. A few weeks later, the day before the Presidential election, we drove deep into the suburbs late at night to adopt a gray tabby that we named Pigeon. Five months after that, we said goodbye to Eris, who had spent the last year wasting away from a slow case of lymphoma. On April Fool’s Day, we welcomed an orange tabby named Momo after she clung to me and cried when her foster human wouldn’t let me take her home immediately. My mind swirled through the end of summer with the strange grief of losing pets and the strange joy of loving them.
Bill Withers – Lovely Day
We got married in a library under an arch of rainbow-colored flowers. Like all the best days of my life, it did not go quite as planned and was perfect anyway. And now I get to be married to my favorite person.
Mitski – Heat Lightning
Just before the pandemic, I bought one ticket to an Elton John concert. Two years later, after multiple postponements, the show finally went on. Somewhere between leaving my seat and reaching the escalator, I lost my phone. After a thorough search and a despairing lost & found report, I took a long, anxious bus ride home. Three days later, after I’d given up and bought a replacement, a custodian found it. I emerged with a nice new phone, a full trade-in refund, and a morsel of faith in humanity.