Wine and Cheese: Lizzy McAlpine and Conan Gray
From hopeless fantasies to chronic obsessions, Lizzy McAlpine and Conan Gray’s shared penchant for creating tearjerkers make them the perfect pair on any in-your-feelings playlist.
It’s your dream collab. The artists you add back-to-back to the queue. The pairing you can’t get enough of. You know they sound good together, but why? Welcome to Wine and Cheese, a series investigating the why and telling you all about it.
Written by Janie Bickerton
Photos courtesy of Harbor Artists & Music and Brian Ziff
Oh, to be young and in love — to have someone to think of all day, to wish goodnight, and repeat the sweet cycle the next day. Lizzy McAlpine and Conan Gray are both young and neither can quite hit being “in love.” For McAlpine, that person turns out to be too reckless, too crude, or a figment of her imagination. For Gray, that person is always tantalizingly close but just out of reach. Through their shared sorrowful themes and similarly patterned sonics, singer-songwriters Lizzy McAlpine and Conan Gray are a great match for anyone hoping to harp on their loneliness, heartbreak, and self-contempt.
Gray’s biggest hit took TikTok by storm in 2020 and literally heralded an (unofficial) national holiday. “I still remember the third of December, me in your sweater,” Gray recalls in “Heather,” a tune that “captures feeling incomparable to the loveliness of a crush’s first choice.” Rather than hating the crush’s object of affection, he wallows in a prison of jealousy and self-loathing: “Why would you ever kiss me? / I'm not even half as pretty.” While McAlpine has no Heather to worry about, she still feels as hopelessly alone as Gray. Although she was more the beloved than the lover, “called you again” sees a puzzled McAlpine feeling hurt because of the pain she inflicted. “Heather” and “called you again” depict their respective singers at either end of a relationship — Gray hopelessly wanting in, and McAlpine having found her way out (almost). “If I don't love you, then why / Did I call you again?” she asks, hoping to make sense of her incongruous patterns. Despite their polarizing positions, one overwhelming sense ties them together: loneliness. They both act out of their unrelenting solitude and hate themselves for it.
The singers find themselves at the same end of the stick in McAlpine’s “doomsday” and Gray’s “Yours,” where both feel used instead of loved. In “doomsday,” McAlpine takes a note from Emily Dickinson’s poetry book and plans her own funeral to convey the power her ex holds over her, even in death. “I'd like to plan out my part in this / But you're such a narcissist / You'll probably do it next week,” she sardonically sings, acknowledging her lack of agency in the midst of her controller, whose substitution of love with power renders McAlpine metaphorically dead but literally used. Gray, however, feels used by someone whom he could never call an ex, but his despair is comparable to McAlpine’s “death.” He opens the song with “I’m somebody you call when you’re alone” (sound familiar?). He knows that this relationship is toxically one-sided, but he refuses to move on: “And I can’t change your mind / But you’re still mine.” While McAlpine takes the metaphorical approach and Gray conveys his position point-blank (“I’m somebody you use, but never own”), both artists give their listeners a song to scream to, to cry to, or to scream-cry to.
Not only do their lyrical themes match, but the sonics and vocals that complete their ballads make McAlpine and Gray even more compatible. From guitar plucks that underlie Gray’s “Family Line” to somber acoustic guitar chords in McAlpine’s “ceilings,” both singers elevate their songs’ sadness with strings. McAlpine even throws in some sultry violin in “called you again” to further drive home her remorse. Just as they implement strings for emotional impact, the singers’ high-hitting vocals transform their feelings from merely symbolic to melancholically tangible. In “Astronomy,” Gray feels as if a relationship has lost its spark, culminating in a heart-wrenching, almost yelled bridge: “You can't force the stars to align when they've already died.” Similarly, the most hard-hitting line of “doomsday” comes in the bridge, where McAlpine loudly admits, “And the funny thing is I would've married you / If you'd have stuck around.” These singers have perfected the tearjerker formula with their somber sounds and their lachrymose lyrics.
While McAlpine spends more time reflecting on past relationships compared to Gray’s dwelling in hypotheticals, both artists avoid living in the present. Scarred by bad experiences with love, they both predict a relationship gone wrong without giving it the chance to bloom on its own. In “reckless driving,” McAlpine fears her carefulness and her duet partner Ben Kessler’s overzealousness will lead them off road. She loses herself in her anxieties, wondering, “If I keep on driving / Would you hold me when we crash or would you let me go?” The parallel lyrics “'Cause I don't love you like that ('cause I love you like that) / I'm a careful driver (I'm a reckless driver)” trip over each other until the song ends mid-lyric, symbolizing the relationship crashing without letting issues bubble over naturally. Gray doesn’t even let the relationship get to the point of reality in his pop anthem “Disaster” — he pictures himself “At the critical chapter where I say, ‘I love you’ / And you don't say it after” before even thinking about asking his obsession on a date. While McAlpine most often uses her failed relationships as fodder, she, like Gray, isn’t afraid to toy with hypotheticals. Gray and McAlpine take their maladaptive daydreaming to the next level by imagining a relationship that never existed. “Movies” offers a glimpse into Gray’s mind, where he’s “dancing in the dark” and sharing a “kiss under the stars” with someone who’s just another “damn fantasy.” In “ceilings,” McAlpine’s most-streamed song on Spotify, she details intimate snapshots of a picture-perfect relationship until the bridge when she reveals that her lover never existed, and she “can’t recall the last time [she] was kissed.” This theme of overthinking love without letting it happen naturally is what makes McAlpine and Gray such a compatible pairing — that is, if you’re hoping to wallow in self-pity.
If crying alone isn’t your scene, McAlpine and Gray have still got you covered. Both artists sprinkle pop jams into their albums to leave listeners not totally bereft of joy. Gray realizes that platonic love is as important as romantic love and hypes up his “ride or die” in his earworm “Best Friend.” Other upbeat hits include his synthy comeback “Maniac” and his party anthem “Wish You Were Sober.” McAlpine takes a more subtle approach to pop infusion. The upbeat “all my ghosts” sees McAlpine head over heels (but in a healthy way), and “erase me” features an electronic bridge produced by virtuoso Jacob Collier. Their sonic experimentation makes room for some feel-good pop that brightens both artists’ mostly morose discographies.
Never quite obtaining the love that they desire, Lizzy McAlpine and Conan Gray represent a generation of hopeless romantics and lonely souls. Their listeners flock to these artists to process their pains, simmer in their emotions, or passionately lip-sync to their hardest-hitting lyrics. Their overlapping themes of young love, loneliness, and endless reeling make them the perfect playlist pair.