It has been six years since Phoebe Bridgers released her last solo album. The monumental Punisher, released in the early days of the pandemic, soundtracked an indescribable period of mourning, political failure, death, and transformation. A fitting album title for a time where it felt like we were all being punished for something we could never be forgiven for. As music critic Sam Sodomsky so aptly put it: “The California native writes songs for moments when things fall apart, when language fails.” Her new album, Lost Weekend, exists in a context no less volatile and apocalyptic.

In the six years between the release of Punisher, Bridgers has been through a lot. Her very public relationship with Paul Mescal came to an end in 2022, and in 2023 she reached the heights of success with her friends and collaborators, Lucy Dacus and Julien Baker, who together form Boygenius, and their Grammy Award-winning debut album The Record. But with success comes the enemy of so many artists: fame. In that same year, Bridger’s father, with whom she had a complex relationship, died. She called out ‘fans’ who bullied her on the way to her dad’s funeral in an interview with Them: “I, at one of the lowest points of my life, saw people who claim to love me fucking dehumanize me and shame me and fucking bully me on the way to my dad’s wake.” During this time, Bridgers disappeared from public life, deeply perturbed by the intense loss of privacy her newfound fame had brought. 

Life is just a series of ups and downs until you die, and Lost Weekend depicts that non-linearity with precision and honesty. The album is not just mournfully sad – it is accepting of what life has to offer, and hopeful too. On one of my favourite tracks on the album, “Haunted”, Bridgers belts: “My heart is growing either way”. This feels impossible after loss, but it is true. You will love and feel joy again, despite it all. 

With collaborators like Jack Antonoff, Alex G, Blake Mills, Conor Oberst, Christian Lee Hutson, her boyfriend Bo Burnham, her pug and many more, Lost Weekend is Bridger’s best album to date. To celebrate the release of her third studio album, we revisited Bridger’s previous work to rank her saddest tracks.

9. “I KNOW THE END”

While I fought for the inclusion of “I Know the End” here, I have my doubts. Is it really best described as sad? I find it euphoric, transcendent, and strangely hopeful for a song about the end of the world. My colleague Halima Jibril initially framed this list as “the Phoebe Bridgers tracks that most make you want to die”, and it doesn’t make me feel like that at all — it makes me want to pack it all in, pile my possessions into a truck and set out for a new life in rural Montana. But then there’s the achingly downbeat first half; lyrics like “you have to go, I know, I know, I know…” and the apocalyptic final note, as the horns sound, Bridgers starts to scream and it all descends into chaos. And while I’m sorry for regurgitating the message of Pixar’s Inside Out, sadness does often come alongside moments of epiphany and resolve (“either way, we’re not alone, I’ll find a new place to be from.”) Unlike some sad songs, “I Know the End” is, for me, less about the crash-out and more about what comes after. It is also among the most vivid and evocative depictions of the US released this century, or ever – no-one else could make the prospect of listening to Kid Rock on a long car drive sound so beautiful. (JG)

8. “NEVER GOING BACK AGAIN!” 

There are several devastating tracks on Lost Weekend, an album about death, the end of things and their beginnings. But “Never Going Back Again!” left me speechless upon my first listen. The haunting, melodic echoes of Bridger’s voice chanting “never going back again, the way it used to be is not the way it is” are immediately juxtaposed with the dynamic folk arrangement in the middle of the song. At first, it feels like a song mourning that things are fundamentally different than they were before, and then it celebrates and revels in that difference. It is the ending of the song that shows you just how complicated these feelings are, when over an instrumental banjo, a sweet voicemail of Bridger’s late father is played. The man who loved her and hurt her again and again. (HJ)

7. “GRACELAND TOO”

If I were to imagine what would soundtrack a road trip through America at 4am, prompted by a mind-melting breakdown, “Graceland Too” would be the only song that feels right. As the tenth track on Punisher, the opening line “No longer a danger to herself or others / She made up her mind and laced up her shoes”, was allegedly inspired by Boygenius’ bandmate Julien Baker and her experiences in rehab. Baker, who grew up in Bartlett, Tennesse, close to Elvis Presley’s Graceland home in Memphis, also sings on the track with Lucy Dacus. There are obviously infinite songs about loving someone with mental health issues, but I find hearing Baker’s soft vocals harmonise with her bandmates on a song about her own suffering so beautiful and different. The line: “she said she knows she lived through it to get to this moment, ate a sleeve of saltines on my floor in my room” has always been a reminder to me that sometimes there’s no pinnacle of “healing”, but it’s still possible in the most mundane moments, like sitting on the floor of your best friend’s room, to remember why life is worth it. (HD)

6. “CHINESE SATELLITE”

There’s a kind of devastating existentialism you can find yourself falling into every few years when you think about your life. ‘Is this all there is?’ I asked myself a few months ago when I fell into depression. The only song I listened to at that time was “Chinese Satellite”. In an interview with Pitchfork, Bridgers explains that the song is about her lack of faith and how desperately she wants to believe in something but can’t. “If I’m being honest, this song is about turning 11 and not getting a letter from Hogwarts, just realising that nobody‘s going to save me from my life, nobody’s going to wake me up and be like, ‘Hey, just kidding. Actually, it‘s really a lot more special than this, and you‘re special.’ No, I’m going to be the way that I am forever.” I remember feeling similarly as a child, as a teen and as an adult. There’s something more going on in this life, right? There has to be. The devastation in this track is just how desperate she is to know, but ultimately knowing that there’s nothing. “I want to believe / instead I look at the sky and feel nothing”. (HJ)

5. “PUNISHER”

The titular track of Bridgers’ sophomore record, Punisher, is a self-effacing, tentative ode to her primary musical inspiration, the late Elliott Smith. Consistently surprising and ambiguous, the song doesn’t just wash over you; it submerges you. A stream-of-consciousness confessional aimed directly at her muse, the chorus comes in the form of a question, which sums it all up: ‘What if I told you / I feel like I know you? But we never met’. Not an expression of grief, it speaks to something more torturous – helpless longing. An eerie dreamscape of wispy backing vocals, floating strings and muted keys capture this potently. The song ends similarly, as we see the ‘punishing’ effect Bridgers’ idolising has on her. Not only does she realise she’s simply a cheap imitation of Smith – ‘A copycat killer with a chemical cut’ – but that if they could meet, she’d ruin it: ‘Wouldn’t know where to start / Wouldn’t know where to stop’. I won’t say the track feels exactly sad, but empty; doomed. (SMC)

4. “WAITING ROOM”

It’s the innocence of “Waiting Room” that makes me tear up every time I hear it. Written when she was 16, Bridgers strums her guitar while delivering simple, searingly sincere lyricism that only a young girl in unrequited love could produce. The utter desperation of one particular line, though, is what hits me the hardest even now: “Wanna make you fall in love as hard as my poor parents’ teenage daughter / She’ll be the best you ever had if you let her”. Wise beyond her years, Bridgers articulates the agony of having a crush more precisely than most adults. And as she attempts to move on, accepting ‘it’s for the better’, the song comes to its bittersweet climax, featuring resounding chords that feel like the final moments in a coming-of-age film. So much more than sad, the ballad is a winding sucker punch straight to your gut – and heart. (SMC)

3. “SCOTT STREET”

“Scott Street” is an anthem for being, like, 23 years old and thinking that you’re soooo washed, your youth is gone and your best days are behind you (which, happily, isn’t actually true!). Bittersweet and wistful, it feels like taking a stroll past an old uni house or through the park in your hometown where you first drank Glen’s vodka and fell in love. In one of my favourite lines, “I asked ‘how is your sister? I heard she got her degree’/ I said ‘that makes me feel old’/ you said ‘what does that make me’?”, it captures the hyper-specific realisation that someone you know’s younger sibling, who you remember as a child, is now a fully-formed person – surely that can’t possibly be the case!? It‘s a deliciously, exquisitely poignant song , which reminds us that sometimes you just have to lean into the existential terror of the passing of time. (JG)

2. “MOON SONG”

There’s a fan-made YouTube video titled “Phoebe Bridgers songs, but they get sadder” and (rightfully IMO) “Moon Song” is the track that finishes it out. The song dwells on the misery of loving someone when you know you’re giving them far more than they’re giving back, but still finding yourself willing to hand over whatever they’ll take. With lyrics like “But you’re holdin’ me like water in your hands” and “And now my feet can’t touch the bottom of you”, this is a heartbreak anthem for when you’re still in the relationship, but one without the usual fiery bridge or biting lyrical hindsight to pull you out of it. Instead, the song leaves you there, heart cracked open and drowning in your own love that has nowhere else to go. (T)

1. “FUNERAL”

A standout track from Bridgers’ 2017 album Stranger in the Alps, “Funeral” is about attending the funeral of “a kid a year older than me”. Already a brutally depressing premise for a track, the song dwells on the complicated emotions that come rushing in when you‘re grieving. The song’s stripped-back production gives Bridgers’ guttingly honest lyricism plenty of room to breathe, as she confronts self-loathing, loss of innocence and the uncomfortable guilt of remaining consumed by her own depression while grieving someone who never got the chance to grow up. (T)