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All of Phoebe Bridgers’ Holiday Singles, Ranked

Many people consider the holidays the happiest time of the year, but, if her music is any indication, Phoebe Bridgers is not among them. Since 2017, the indie singer-songwriter has released a new seasonal cover annually, accumulating a collection that is a far cry from the joyful cheer typical of holiday tracks. Bridgers’ holiday repertoire instead consists entirely of melancholic tracks, often dealing with themes of loneliness, mental health, and the impact of social issues within the context of Christmastime. While consistently sorrowful, these tracks exhibit a haunting beauty that reflects Bridgers' skill and growth as an artist. Oftentimes touching on important societal problems, many of these tracks also extend support to those struggling during the holidays, validating one’s sorrow and offering the comforting sense of not being alone. A gloomy yet excellent alternative to the season’s usual cheer, here’s a complete ranking of all of Phoebe Bridgers’ holiday singles.


Bridgers opens her 2020 EP, If We Make It Through December, with its titular track, a choice that sets the record’s despondent tone. The first of the EP’s four holiday covers, “If We Make It Through December” is a rendition of a 1973 track recorded by American country artist Merle Haggard and the Strangers. Even for Bridgers, it’s a bleak cover, dealing with themes of loneliness, poverty, and unemployment, as its storytelling lyrics chronicle a financially struggling family attempting to stay afloat during the holidays. The original song is lightened by its upbeat country sound, with a swinging tempo and buoyant vocals that seem completely at odds with the lyrical narrative, but in typical fashion, Bridgers’ cover instead doubles down on the misery at hand. Backed by soft piano chords, The artist’s soft vocals sound almost frail, conveying a desperation befitting of the song’s lyrics. Her delivery is fraught with emotion, and the repeated assertion that, “If we make it through December we’ll be fine,” sounds more like a hopeless plea than an optimistic promise. The track’s production holds an echo-like quality that at times, almost seems to mimic the harsh winds of December, conveying the bleakness of not only the song’s season but its situation as well.


The second track off Bridgers’ If We Make It Through December EP, “Day After Tomorrow” continues the despondent tone set by its opening track. Originally released in 2004 by Tom Waits, the song is written from the perspective of a soldier away at war and is loosely formatted as a letter written home, with the speaker recounting the hardships of day-to-day life. Bridgers’ cover is sparsely instrumented, consisting mainly of soft piano chords and echoing strings that create a haunted atmosphere. This troubled quality is also reflected in Bridgers’ somber vocals, which convey a dispirited sense of misery throughout the track. Pining mournfully for home, the song’s narrator is troubled by the uncertainty of ever returning. The lyrics’ existential turn is reflected in Bridgers’ wavering vocal delivery, asking, “How does God choose? / Who’s prayers does he refuse?” Achingly woeful, the cover is equally as tragic as it is gorgeous.


On 2023’s “The Parting Glass,” Bridgers is joined by Irish folk duo Ye Vagabonds, as well as her own band, Boygenius. An indie rock supergroup, Boygenius saw a year of breakthrough success with the release of their debut album The Record, receiving several Grammy nominations and embarking on a sold-out U.S. tour. It therefore comes as no surprise that Bridgers saw fit to enlist her Boygenius co-members, indie singer-songwriters Lucy Dacus and Julien Baker, for her most recent holiday single. “The Parting Glass,” is wistful and melodic, opening with soft orchestral strings and moving into a ballad sung by Bridgers, Dacus, and Baker in equal parts. Sparsely instrumented, the track is almost acapella at times, but the trio’s lush harmonies fill the empty space. Haunting and beautiful, “The Parting Glass” is a testament to the collective musical power of Boygenius.


Bridgers’ 2019 cover of Dan McCarthy’s “Christmas Song” is subdued in gloom but strikingly beautiful nonetheless. The track is lyrically introspective, reflecting on the peculiar sensations of loneliness and sorrow that Christmastime can bring. Beginning in quiet contemplation, Bridgers’ voice builds up until she is almost belting with her final, emotional delivery of the line, “You don’t have to be alone to be lonesome.” The song’s instrumentals convey the track’s growing emotional tension, shifting from mellow piano chords to swelling strings and increased percussion. Lush background harmonies accompany Bridgers as she mournfully reflects that, “The desire for annihilation / is as common as it is unkind.” The instrumental addition of jingling bells conveys a festivity that feels almost ironic against the song’s sentiment. Bridgers’ version of the track is strikingly melodic and encapsulates the isolating nature of one’s sadness amidst seasonal joy.


Bridgers’ 2022 Christmas cover of The Handsome Family’s “So Much Wine'' is an invigorating departure from the bleakly despondent nature customary of her holiday singles. Despite its melancholy lyricism, the 2000 track holds a liveliness that comes through in Bridgers’ breezy rendition. Although Bridgers begins in typical downtrodden fashion, with her soft vocals accompanied by a plucking acoustic guitar, but the track picks up with the onset of its first chorus. Twirling fiddles, jaunty whistling, and the presence of a steady drumbeat (uncommon for a Bridgers song) create an uptempo sound that sonically resembles a traditional folk dance. Her dreamy voice carries an uncustomary lightness and contrasts vibrantly with the low backing vocals of her then-boyfriend Paul Mescal. Although not without its melancholy – it is Phoebe Bridgers, after all – the song is permeated by an undercurrent of sweetness as well. The lyrical account of a partner’s alcohol abuse is grounded in introspection, rather than judgment or anger. “Listen to me, butterfly / there’s only so much wine that you can drink in one life,” Bridgers sings, sounding forlorn but gentle. While more somber than the original, Bridgers’ take on “So Much Wine'' is a refreshingly vibrant addition to her holiday collection.


“Have Yourself A Merry Little Christmas” has always been tinged with sadness, so it follows that Bridgers’ characteristically downbeat sound renders her 2017 cover downright depressing. But that’s not to say that Bridgers’ take on the holiday standard is without its unique merit. Originally composed in 1944 and performed by Judy Garland, the song has since been covered by scores of artists, ranging from classic jazz artists such as Frank Sinatra and Bing Crosby to modern pop stars such as Michael Buble and John Legend. Bridgers’ rendition, however, is set apart by its undisguised sorrow. Rather than concealing the song’s bittersweet undertones with upbeat instrumentals and sunny vocals, as many artists have attempted to do, Bridgers draws out its hidden melancholy. The subdued wistfulness of the track’s stripped-back, acoustic instrumentals concentrates attention on Bridgers’ vocals, emphasizing the lyrical contents. Dreamy and yet piercingly clear, Bridgers’ vocal delivery infuses each line with heartrending emotional vulnerability. Distinctively melancholy and yet shot through with beauty, “Have Yourself A Merry Little Christmas” ranks amongst Phoebe Bridgers’ best covers. 


Nowhere is Bridgers’ hauntingly melancholic sound more prominently displayed than on the heartbreaking yet poignant “7 O’Clock News / Silent Night.” Alongside collaborators Fiona Apple and The National’s Matt Berninger, Bridgers’ 2019 cover puts a fresh spin on the track. The original song, released in 1966 by singer-songwriter duo Simon & Garfunkel, juxtaposed the classic Christmas carol “Silent Night” with a news report on events ranging from congressional debates over the Civil Rights Bill to protests against the controversial Vietnam War. Maintaining the same basic format, Bridgers, accompanied by Apple, opens the track with a starkly beautiful rendition of “Silent Night.” However, the contents of the track’s simulated news broadcast, read by Matt Berninger, deviate from the original. Berninger reports on contemporary events, covering topics such as a Supreme Court review of a restrictive Louisiana abortion law, testimony given in Donald Trump’s impeachment trial, and racially motivated police brutality. Initially a barely perceptible background drone, Berninger’s voice becomes progressively louder throughout the track, until Bridgers and Apple are buried beneath his monotone recitation of tragedy after tragedy. Sadness can be easily ascribed to most of Bridgers’ covers, but what makes “7 O’Clock News / Silent Night” stand out is the particular quality of its sadness. The hopeful simplicity of “Silent Night” as it is drowned out by the suffering the modern world holds conveys a metaphorical quality, reflecting that even amidst the joyful spirit of the holidays, larger suffering remains at hand. The track is a pessimistic reminder of the weight of our collective fears and sorrows, a burden that the holiday spirit can do little to alleviate. 


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