illustration by Brianna Ashby

Paul Simon was never not in my life. It started with Simon & Garfunkel, of course, Bridge Over Troubled Water blaring from the tape deck of my family’s Dodge Caravan. As a troubled college student, I spent many late nights with “I am a Rock,” absolutely certain that nobody would ever understand. I’m older now, and I get that lyrics like “I have my books and my poetry to protect me” are best sung as over-the-top-dramatically as possible, preferably while wearing a black turtleneck and clutching a leather bound volume to your chest. I still go for the occasional late-night cry-along, and I still turn to Paul Simon more than any other artist. Every winter, I reliably embark upon a full-catalogue deep-dive to soothe/supplement the seasonal depression that threatens to cut me off from the world. When January rolls around and February looms darkly ahead, Paul Simon is the old friend I can count on to get me through. The world loves Paul Simon, and I love him dearly, deeply, indiscriminately, so it pains me to say what I am about to say: Paul Simon is a terrible actor. Thankfully, he hasn’t acted much.

There were incidents and accidents/There were hints and allegations

In Annie Hall, Paul Simon shows up as wide-collared record producer Tony Lacey, stroking Annie’s hand after she sings “Seems Like Old Times” in a club. “It was very musical,” he says of her performance. “I liked it a lot.” As an actor, Simon is sibilance on legs, all small-statured and soft-spoken. “We’ll be very mellow,” he says when he invites Annie and Alvy Singer to a party, as though this leering leisure suit could be anything but. As Tony Lacey, Simon is quiet and calm to an irritating degree—no wonder Alvy hates him from the start. Simon is no good at playing anyone but himself, and while I can’t praise his acting in Annie Hall, I can say that his oddness suits the part. The last time we see Tony Lacey, he’s dancing with Annie in front of a white Christmas tree, doing that sly Paul Simon side-smile and gently twisting his hips. What a creep.

Three minutes of comedic screen time in Annie Hall is one thing, but it’s much harder to take Paul Simon seriously for ninety minutes of One-Trick Pony, the 1980 film he wrote and starred in. One-Trick Pony is the more-than-semi-autobiographical tale of a singer-songwriter about Simon’s age, with about Simon’s history of success, and about Simon’s personal life at the time the movie was being made (estranged wife, one son, string of mistresses, uncertain recording career). The movie follows Jonah Levy (Paul Simon) on tour with his band, playing “ordinary rhythm and blues, your basic rock and roll” before groups like The B-52s take the stage with their hip new 80’s sound. It’s compelling subject matter: an artist going through a mid-career slump, weighing youthful dreams of stardom against the demands of family and encroaching middle age. But the film itself is shapeless and boring. Jonah mopes around, plays a few gigs, has a few flings, and records an album with with a hot-shot producer played by Lou Reed. Reed is the best musician-turned-actor in the starring vehicle Paul Simon wrote for himself.

Despite Simon’s amateur screenplay and questionable acting, One-Trick Pony does have one thing going for it: a soundtrack full of Paul Simon songs. The biggest hit to come out of the soundtrack is “Late in the Evening,” but my favorite is the title track, a bluesy rock song in which the metaphor is in no way veiled: ‘He’s just a one-trick pony, that’s all he is, but he turns that trick with pride.” Where One-Trick Pony the film is a self-serious slog about a troubadour in crisis, “One Trick Pony” the song is a tight, rhythmic encapsulation of the same, more effective in less than four minutes than the movie is in over ninety. In the film, “One Trick Pony” is performed live at Cleveland’s Agora Ballroom, “Jonah” and his band framed up close, sweaty and smoky under the stage lights. It’s the closest Simon gets to sexy, dripping sweat and speak-singing in a dark club, decades away from the seated theaters and amphitheater shows I would see as a teenager and young adult. I can only speak for myself, but Paul Simon’s appeal has never been as a sex symbol, and despite One-Trick Pony‘s best attempts to frame him as a highly-desired womanizer (written by the man himself, of course), to me he still comes off as a charming eccentric with a slight edge of creep. I don’t want to see the man shirtless, I just want to hear him sing. Like the song says, “when he steps into the spotlight/You can feel the heat of his heart,” and it’s that heart that gets me every time.

One-Trick Pony was a colossal flop, and it was followed by the least-acclaimed album of Simon’s career, 1984’s Hearts & Bones. The early 80’s were the nadir for my man Paul. And yet, out of the ashes of his middle-age crash and burn came his greatest triumph, 1986’s Graceland, one of the most critically and commercially successful records of all time. I find comfort in the story of Graceland, a perfect work of art that came about as the direct result of artistic and personal failures. If Simon hadn’t made a self-indulgent, solipsistic film about a singer-songwriter in crisis, and if that film and his subsequent album hadn’t flopped, and if his marriage hadn’t also failed around the same time, he never would have traveled to Africa and written about a “soft in the middle” “stranger in a strange land” called to account for his sins. Graceland is Paul Simon’s flawless self-absolution.

“The way the camera follows us in slo-mo/The way we look to us all”

Despite his failure as a screenwriter and actor, Paul Simon has managed to make an indelible impact on film. The man has amassed over 200 music credits in films and television over the past 50 years, his songs as ubiquitous in media as they are in my memories, showing up everywhere from The Graduate (1967) to Wild (2014). Paul Simon songs are shorthand for loneliness, connection, global curiosity, spiritual ambivalence, and the sweet ache of memory; he’s the perfect supplement to a certain kind of film.

My top five film moments prominently featuring Paul Simon tunes are as follows (yours may vary):

5. Garden State (2004), “Only Living Boy in New York”

Say what you will about Garden State; there is a lot to say. I’ve been carrying a DVD copy in the trunk of my car for almost two years, and it’s become a favorite joke of mine to offer it to anyone who happens to be with me when I pop the trunk: “Can I interest you in a DVD copy of Garden State, written by, directed by, and starring Zach Braff?” Trust me, it kills (just kidding, my friends hate me). As a younger woman, I fell prey to its emotional manipulation, but now that I’m a grown-up, I realize Garden State kind of sucks. But so help me, I still love the scene where Zach Braff and Natalie Portman kiss in garbage bag ponchos as Paul Simon sings “let your honesty shine, shine, shine.” Simon famously wrote “Only Living Boy in New York” about Art Garfunkel going off to film a role in Catch-22 and leaving Simon behind to write songs for Bridge over Trouble Water, which would become their most acclaimed–and final–collaboration. The song is all love, respect, and resentment at the edge of the infinite abyss.

4. Almost Famous (2000), “America”

“This song explains why I’m leaving home to become a stewardess,” Anita says, lowering the needle on Bookends. “America” is the soundtrack to her leaving home, and leaving her little brother William behind. As her boyfriend loads up the car, she leans down, takes William by the shoulders, and says, “One day, you’ll be cool.” Then she whispers close to his ear: “Look under your bed. It’ll set you free.” This scene signals the beginning of William’s lifelong obsession with rock ‘n’ roll, and the entire thrust of Almost Famous. As Paul Simon sings about seeing America from a bus with his girlfriend, William pulls a satchel full of records out from under the bed and caresses the cover of each one: The Beach Boys, the Rolling Stones, Led Zepellin, Jimi Hendrix, Cream, Joni Mitchell, Bob Dylan, the Who. In a few moments, the film will flash-forward a few years to William setting off on tour as a journalist for Rolling Stone, seeing America from a bus with a band and learning the difference between fan and journalist, and journalist and friend. But in this early scene, he’s just getting started. “And the moon rose over an open field,” Paul Simon sings, as William’s world is illuminated by a stack of records on the bedroom floor.

3. Obvious Child (2014), 

Director Gillian Robespierre has been quoted all over the place saying, essentially, that people can draw whatever meaning they want from the title of her film. Obvious Child is a romantic comedy that includes an abortion, and “the obvious child” may be the zygote the main character temporarily carries, or the character herself. Or maybe it’s just a fantastic song. On choosing “Obvious Child” to score and title the film, Robespierre told The Wire: “It was just a song that I listened to a lot in the car when I was little.” In the film, Jenny Slate and her one-night-stand-turned-maybe-more turn it up loud. It’s hard to capture the feeling of a great songs in words, but two drunk twenty-somethings in the beginning stages of like, air-drumming and jumping on the couch to a beloved beat from childhood: that says it all.

2. The Royal Tenenbaums (2001), “Me and Julio Down by the Schoolyard”

The Royal Tenenbaums came out in the winter of my 19th year, and I must have seen it in the theater at least 15 times. It was a rough time for me (remember those late-night sob-sessions to “I Am a Rock”) and the film’s release coincided perfectly with my first extended break from college. Almost every day for two weeks, I went to a matinee screening, sometimes two in a row. As in all Wes Anderson films, the songs in The Royal Tenenbaums are essential, each one perfectly placed to complement and complicate the story. I still have the journal (of course I kept a journal) in which I tracked my observations and feelings about the film, and one of the notes reads: “Me & Julio = New York boy sings about mischief while New York boys get into mischief.” The frenetic rhythms and juvenile delinquency narrative of “Me and Julio Down By the Schoolyard” underscore Royal, Ari, and Uzi Tenenbaum “takin’ it out and choppin’ it up.” They run in the pool area, jay walk, jump horses, go-kart, throw water balloons at passing cars, shoplift, hitch a ride on the back of a garbage truck, and bet on dog fights on the bad side of town. It’s a classic Andersonian montage of boys up to no good, an emotional and comedic highlight of my forever-favorite emotional comedy.

1. The Graduate (1967), “The Sound of Silence”

Could there be any other choice for Top Movie Moment Prominently Featuring a Paul Simon Song? The Graduate is a classic, of course, and Mike Nichols chose Paul Simon personally to soundtrack the entire thing. There are so many wonderful scenes to choose from, but as I’m making a case for Simon’s indelible contribution to film history, I have to highlight the second-act “Sound of Silence” montage where Benjamin pulls himself out of the pool and into bed with Mrs. Robinson. In television performances during the late 1960’s, Simon & Garfunkel often introduced “The Sound of Silence” as a song about “the inability of people to communicate, not only on an intellectual level, but on an emotional level as well.” Their earnestness is a bit laughable now, but Simon was in his early twenties when he wrote the song, not much older than earnest Benjamin Braddock, so of course it’s the only choice to score Benjamin’s summer of drift and lust.

“As if everybody here would know what I was talking about”

Throughout his 60+ years of songwriting, Paul Simon has written about big ideas, the hard part of relationships, parenthood, politics, and God. Sometime it’s a little overwrought, but usually it’s familiar and uncanny, full of sentiments I recognize when I hear them but could never articulate myself. My favorite thing about Paul Simon is the way he talk-sings, pulling the listener into a musical conversation that feels like listening to a friend. He’s knowing without being condescending, and his side-smile and shrug let us know he’s on our side. Paul Simon knows what we know, you know?

Some sad day in the not-distant-enough future, Hollywood will make a biopic of the late, great Paul Simon. Perhaps Jason Schwartzman will star. Josh Groban would make a pretty good Garfunkel. The famous sons and daughters of Paul Simon’s famous friends can play younger versions of their parents, dressed in period costumes and wigs. If we’re lucky, it will be something compelling and unique, more I’m Not There than Walk the Line. If we’re not, it will be an overblown Hollywood affair, manufacturing drama where there was little or none. The details of Paul Simon’s real life are rather boring: a musical kid, a combination of hard work and lucky breaks, a few romances, an up and down career. Chances are, the movie won’t be great. But with any luck, and the permission of his estate, it will be full of Paul Simon songs. And oh, those songs.

Elisabeth Geier is a writer, teacher, & etc. living in Portland, Oregon. She has previously lived in Dallas, Oregon; Missoula, Montana; Chicago, Illinois; Boston, Massachusetts; and Lafayette, California. She would be happy to direct you towards the best pizza in these locations.