I wrote an issue recently about 100 the end, about how I thought it would be the last playlist I’d make. I thought I’d wrap up my project with a tidy bow and a clever last word.
Obviously, I changed my mind. In the few days after I finished this playlist, I realized how much I missed organizing my listening habits into bite-sized mixtapes. I couldn’t actually remember how I consumed to music before playlists; did I put on an album and listen start to finish, or choose songs at random, pausing to peruse the vast array of music at my fingertips every five minutes?
I remember when I made this playlist, it was the beginning of the summer. I was feeling optimistic about the future—my senior year, a budding relationship, a relaxing break, the imminent realization of my college-related dreams. This playlist, perhaps more than any other, has such a strong temporal hold on me that it is transportive. These songs represent a time in my life that was full of possibility and longing.
“Me and Julio Down by the Schoolyard” begins with an iconic guitar part. It’s cheerful to the point of jubilant; the rhymes are short, the form is clear, the melody is major, the vocals are done in chorus. It features a cuica, a Brazilian friction drum, and whistling. For 1972, this song is incredibly short, coming in at only 2:44. It’s like a piece of citrus in the summer: refreshing, precious, and sweet.
The meaning of the song is highly contested—lewd sexual act, general teenaged misconduct, something horribly gruesome. In a 1972 Rolling Stone interview, Simon said that “what the mama saw” was of little consequence to him, in fact, prior to the interview he hadn’t thought of it at all. I like this interpretation because it flies in the face of the modern obsession with concrete backstory, with truth. I’ll be the first to admit that I’m caught up on every detail of the Olivia Rodrigo-Joshua Bassett drama, and I know who every Taylor Swift song is allegedly about, but I respect Paul Simon’s commitment to the value of his music without a real-life inspiring event, without the world building that fans now expect of artists. This song is an absolute bop, why does it need to mean something too?
Meanwhile, “Take the Box” faithfully chronicles Amy Winehouse’s breakup with her former boyfriend prior to the release of her debut studio album Frank (2003). She refers obliquely to a Frank Sinatra CD, which had been a Christmas present, as well as a gifted Moschino bra. Her mother, Janis Winehouse, wrote in her memoir that Amy was so young at the time of this breakup that she was living at home, and couldn’t drive to her boyfriend’s house herself. She sat in the passenger seat of her mom’s car with a box of her teenaged boyfriend’s belongings and then wrote “Take the Box.” Frank came out when she was twenty years old. She was only twenty seven when she died.
Everyone knows that Amy Winehouse’s story is tragic. She was let down by the media, by her management team, by her fans. It’s unproductive to rehash how everyone failed her, but it’s worth acknowledging that not only was she vulnerable because of her struggles with her mental health and substance abuse, she was also incredibly young. The emotion she conveys in her incredible vocal performances is far too deep for someone her age. She was forced to grow up fast in an effort to keep up with her outsized fame, fame which had its own momentum and centered on an idealized, unattainable figure separate from Amy Winehouse, the girl. Severed from her identity as a young person, trying to figure things out, her highly publicized battle with addiction aged her public image and cost her the compassion and help she deserved and needed.
Tobias Jesso Jr. decided to avoid fame entirely. He was discovered by Adele, who tweeted a video of his song “How Could You Babe.” After that, his debut album Goon (2015) reached No. 7 on the Alternative Albums chart, he booked late night TV show appearances, and was named Songwriter of the Year at the 2015 Juno Awards. He was gaining traction rapidly, on a trajectory to super-stardom.
After about half a tour supporting Goon, he told his managers he was going home and would not do any more interviews. He simply did not want to be famous, or to be a solo artist at all. He said that his end goal was to write for Adele, and when she discovered him almost immediately, he decided to hang his hat as a performer and stick to writing. He co-wrote “When We Were Young,” Adele’s stand-out ballad on 25 (2015) and has since worked with Sia, Pink, John Legend, Charlie Puth, Florence + the Machine, and HAIM, among others. He’s got a wife and a kid and likes to “take time away” from his busy songwriting schedule in Los Angeles.
As an early fan of Goon, of course I wish Tobias Jesso Jr. would have given us more solo work. That being said, I wonder often what Amy Winehouse would be doing now had she been swiftly removed from spotlight and given a normal life, a real shot at fully developing her prefrontal cortex and becoming an adult. Our refusal to treat celebrities as people, because we believe dehumanization is the price of fame, cost Amy Winehouse her life. I hope that we give the young folks coming up in the music industry (breakout stars are getting younger and younger) more respect, privacy, and grace. I hope we endeavor to protect them from everything we can.