Da 50 Songs - Part One

50 (of the) Best Songs of the Last 20 Years

I was just sitting here in my rented room in Studio City, CA ruminating on my impeccable taste.  I’m a bon vivant.  A flâneur.  Something they only have words for in French.  I am inherently right, and when I’m wrong I’m so delectably wrong that I am also somehow right.  It’s a magic trick you cannot learn.  And so it is with this unparalleled discernment I offer you my list of da 50 best songs from the last 20 years.

This list is irrefutable because it is MY list, and I made the choices.  Additional people were polled and their responses were ignored.  Just vibe with it and listen to some music.  And post your own 50 songs if you want your opinion known. 

I don’t know why I did this.  Nobody was asking for it.  But it seems as though sharing music is one of my “love languages.”  So I guess I love you.

Finally— I’m not here to argue the validity or merits of ranked lists.  I don’t caaaaaaare.  Pretty much everything is subjective, so baby calm down.

50

Dave Matthews Band, ‘Spaceman’

2012

WRITER(S): Carter Beauford, David J. Matthews, Stefan Lessard

Please, have mercy.  Position #50 is for DMB, and you’re all lucky I didn’t put it at #41 (Google that if you didn’t just laugh).  Here in the year 2024, DMB are no longer busting out the horndog, energetic Virginia-south jam band rock they became an entire genre and cliche for.  The members of DMB are all over middle-age now, and the mellowness of their later catalogue reflects that.  In 2012, on their first studio album following the passing of irreplaceable founding saxophonist phenom LeRoi Moore, it was impossible to predict how DMB would react tonally.  Pared with slightly more moments of soft, nostalgic introspection, the sound on Big Whiskey and the GrooGrux King (named in honor of Moore) remains fundamentally DMB, almost in defiance of LeRoi’s premature death.  He’s still with them in the arrangements.  You can almost hear the moments in song where the band might have thought to themselves, “How would the GrooGrux take this up a notch?”  On “Spaceman” Dave perfectly performs his signature hedonist with a heart of gold.  Carter Beauford is DEEP in his drum bag.  These men have grown up, grown older, and lost together, all while gaining and maintaining enormous success and watching a world largely fumble and flail around them.  

Essential lyric: All the freaks are on parade // I wanna fill my belly, so I gotta get paid // Doesn’t everybody deserve the good life?

49

Eli Pafumi, ‘Rock n Roll Dream’

2023

WRITER(S): Elijah Pafumi

A fair-ly scathing but ultimately earnest and empathetic critique of social media and modern music marketing/promotion.  This tune is a rollicking, catchy call to living in the real world and making art as a medium of community.  For all the folks who grew up with dreams but got lost in the game of validation and appearances.  More timely now than ever.  

Essential lyric: Follow me up now, baby // The 1’s and the 0’s ain’t friendly // Tick, tock on the clock // before you’re benign // Our days are timed

48

Runnner, ‘Eggshell’

2019

WRITER(S): Nate Lichtenberger, Noah Weinman

A lo-fi melodic journal entry sublimely capturing the daily, granular anxiety of young-ish adulthood in a disillusioned, economically limited America.  East LA ennui featuring banjo and a surplus of quotable lyrics for its intended SSRI-riddled audience.  

Essential lyric: I hate the part of the song where the chorus hits // ‘cause I don’t like sticking flags on my nervousness

47

Blind Pilot, ‘Go On, Say It’

2008

WRITER(S): Ryan Dobrowski, Israel Nebeker

With a shuffling drumbeat that sounds like a car engine thrum alongside dotted white lines of acoustic guitar strums, “Go On, Say It” is a relatively revealing portrait of its singer/narrator.  We hear how deeply one can internalize observations put to them; how much our use of language, our choice of words can impact and potentially devastate.  By the final time frontman Israel Nebeker calls for the song’s recipient to “say it right,” it sounds less like a plea and more like a principle.  

Essential lyric: A hitchhiker told me I don’t talk a lot // It made feel fine // It made me quiet

46

Josh Ritter, ‘To the Dogs or Whoever’

2007

WRITER(S): Josh Ritter

Blending his typically novelistic lyrics with a punchy, consonant-hitting folk delivery, Ritter gets a whole lot of words in here, and somehow makes them all work.  He’s cramming in syllables, internal rhyme schemes, and at times seemingly about to run out of breath— all adding to the momentum that gives the song its urgency.  In another life Ritter could be writing some really wack rap bars.  A story about literary, historical, and biblical figures all blended into a montage of iconoclastic love.   Also, what the hell is that sound in the breakdown towards the end?  A whip crack with reverb?  A gunshot?  It’s great.  

Essential lyric: Through the wreck of a brass band // I thought I could see her // In a cakewalk she came // through the dead and the lame // Just a little bird floating on a hurricane

45

Molly Sarlé, ‘Human’

2019

WRITER(S): Molly Erin Sarlé

A tune that sounds like a lost, early-era Stevie Nicks’ track, but trades the Laurel Canyon backdrop for Woodstock, NY by way of Big Sur.  Recorded in an 1896-built church-cum-studio whose ethereal atmosphere helps evoke humanity reaching for the heavenly, the song speaks to the (oft unrequited) lovers we turn into legends.  Sarlé’s voice and writing have a genuine, timeless quality to them, and the whole recording is buoyed by a beautifully bubbly bass line by Brian Betancourt.  Given a stamp of approval by none other than songwriting giant Jeff Tweedy who said, “I think that it has the hallmarks of a great song in that you want to hear it again when it's over.”  

Essential lyric: Well, who hasn’t talked to God like he’s a man? // I do it all the time // on accident

44

JR JR, ‘Philip the Engineer’

2015

WRITER(S): Joshua Epstein, Nicholas Ruth, Daniel Zott

Have you ever heard a 3.5 minute pop song about a post-apocalyptic, underground civilization unwittingly on the verge of collapse?  There might just be the one.  An example of perfectly concise, wonderfully melodic pop storytelling.  A warning against ignorance, and a thoughtful recognition of the loss of innocence.  Corroborated by massively-streamed tunes like “Gone” and “The Way I Do,” the two lads of JR JR are clearly masters of songcraft, and here they lean uniquely into their ability.  Maybe it’s because I read City of Ember in elementary school, but “Philip” really builds a whole world for me sonically.  

Essential lyric: Should I tell the truth // if you’re not ready? // I don’t want to be the one // who says it’s broken // But somebody’s gotta tell it like it is

43

The Weakerthans, ‘Sun in an Empty Room’

2007

WRITER(S): Stephen Carroll, John K. Samson, Greg Smith, Jason Tait

Drawing inspiration from the Edward Hopper painting of the same name, “Sun in an Empty Room” is the ultimate relationship post-mortem.  As the song’s narrator details the light in a vacant apartment and all of the love, tumult, and potential that once existed inside of it, we invariably conjure our own departures and sliding door alternate lives.  At times we move on because we’ve outgrown our context.  Sometimes we’re forced to move on because our context has outgrown us.

Essential lyric: Take this moment to decide // If we meant it, if we tried // Or felt around for far too much // From things that accidentally touched

42

Hellogoodbye, ‘Would It Kill You?’

2010

WRITER(S): Forrest Kline

Predominantly under the nose of the mainstream, Hellogoodbye has been making some of the best indie rock of the last 15 years.  Diehards might say “20 years” and include Zombies! Aliens! Vampires! Dinosaurs! on that list, but it was with Would It Kill You? in 2010 that Hellogoodbye focused its sound and cemented itself as an indie pop project with serious dimensionality.  Incorporating his now-regular/regularly foundational acoustic meets electronic “bedroom orchestra” (arrangement-style) for the first time, Hellogoodbye’s sole songwriter + frontman Forrest Kline came into his own on WIKY? as a less-unwieldy Brian Wilson for the home recording age.  If that sounds like a stretch, throw on “Honeymoon (Overture)” or “Coppertone” and awash yourself in the lush string sections.  On the title track from WIKY? Kline employs surf-inflected drums, tack piano, synth blasts, violin runs— and fuses them all seamlessly into pop rock bliss.

Essential lyric: It’s so hard to spend all winter // wanting summer like you couldn’t bear the cold // Six months later // it’s a bummer like it instantly got old

41

Fiona Apple, ‘Relay’

2020

WRITER(S): Fiona Apple, [sample from “My Kettle My Cats”] - Sebastian Steinberg

Fiona Apple is entirely herself, and that’s exactly what people love or find off-putting about her.  She recognizes this, embraces it and/or deals with it.  When Apple somewhat surprisingly released her first full-length in 8 years, 2020’s Fetch the Bolt Cutters, she finally seemed content to satisfy her spirit, her vision alone.  On an album filled with knotty, circuitous verses, “Relay” takes its loop and runs laps with it featuring a sinister, grooving bass line, and Apple’s own harmonies + backing vox crouching in the periphery of the audio field like wolves circling the track.  Apple told The Guardian of the final a cappella lines that close the song: “I was starting something but I never picked up on it.  It seems like what I was trying to say is: it’s a lot of work to try to forgive.  And I’m really trying.  I think I was thinking of all the different ways throughout my life that I’ve tried to not fall into despair and rage – because it’s so scary sometimes to get so angry.  Especially if you’re somebody who turns your anger in on yourself, it’s dangerous to be angry sometimes.  People lay their shit on you and they walk away and you’re left with mountain after mountain to climb, trying to figure out how to be in the world and manage all this rage.”

Essential lyric: I’d love to get up in your face // But I know if I hate you for hating me // I will have entered the endless race

40

Elliott Smith, ‘A Fond Farewell’

2004

WRITER(S): Elliott Smith

Another Portland native writing about Elliott Smith…  Please forgive me.  I have some connection and bias here.  Yes, I “liked Elliott before you.”  Or I didn’t.  I don’t know your life.  But I am from Portland, Oregon where he chose to reside and make music for many years.  And I did relocate to LA, as he did in 1999 to make good on the grander musical visions in his head.  All of that said, I am not on par with Elliott or even many people who have already written about him, but I am a deep, genuine fan.  Elliott spoke to my soul early on.  First it was “Waltz #2” on a mix CD made for me by a dear friend.  Then I read that one of Ben Folds’ favorite albums was Either/Or (he went on to write “Late” from Songs For Silverman about Smith posthumously.)  I wish I could truly relate more about Elliott’s magic, but it’s there in his songs.  You can simply listen.  Madonna said she wished she’d written “Behind the Bars” but the song selected here (truthfully due in part to the 20-year cutoff) is “A Fond Farewell.”  By the time this song was released, Elliott’s voice was already a ghost haunting us all.  A beautiful, chilling contemplation on the nature of an addict and their relationship with the object of their addiction.  A doomed affair.

39

Cheekface, ‘I Only Say I’m Sorry When I’m Wrong Now’

2019

WRITER(S): Mark Edwards, Gregory Katz, Amanda Tannen

Slacker activism (Slacktivism??) by older Millennials for the Gen Z era.  Quite prolific in their output, dropping four full-lengths and two b-side compilations since their debut LP Therapy Island in 2019, co-writers Amanda Tannen and Greg Katz seemingly have enough to say to fill millions of DSA zines or MAD mags.  Hook-laden, humorous, and replete with cowbell.

Essential lyric: I only say I’m sorry when I’m wrong now // I only run the air when it’s warm out // I only text the friends that I like now

38

Jack Symes, ‘Cool God’

2019

WRITER(S): Jack Symes

Not the only song on this list to address the divine, but probably the one to go about it most directly.  Indie folk singer-songwriter Symes turns in a gently heartbreaking inquiry to the big man upstairs, and his answers, or lack thereof, come up wanting.  Evoking the murders of cultural icons John F. Kennedy and Marvin Gaye to tap into our sense of shared, inherited grief becomes a brilliant bridge choice to connect the personal to the sensational to the biblical.  From an album recorded in a converted Spartan trailer on the coastal bluffs of Santa Barbara, the entire ethos of the song drips with shaggy, hopeful mortality.  

Essential lyric:  And what’s the point of forgiving // us for the sins we won’t stop making? // It must take up your time

37

Miley Cyrus, ‘Jaded’

2023

WRITER(S): Sarah Aarons, Miley Cyrus, Greg Kurstin

Miley Cyrus has always been a chameleon.  She started her career by playing two people on Hannah Montana— an everyday “Girl Next Door” + a teenage pop star.  She has since gone on to be Bangerz Miley, the rebel Country Music queen inherit Miley, and on “Jaded” she is Miley as filtered through the sound and soul of Melissa Etheridge.  It is powerful and anthemic.  It’s maybe the best version of Miley yet.  

Essential lyric: It’s a fuckin’ shame that it ended like that // You broke your own heart // But you’d never say that

36

James Vincent McMorrow, ‘Red Dust’

2013

WRITER(S): James Vincent McMorrow

Beginning his musical journey behind the drum kit at 15 playing mostly metal, it wasn’t until his later teens that JMV “…started listening to older music from the 50's-70's, and learning guitar, piano.  Then I heard a Donny Hathaway song called ‘I Love You More Than You Will Ever Know’ and it made me want to start singing.”  “Red Dust” makes it difficult to imagine a world where McMorrow didn’t find his voice.  Like a prayer delivered softly to the stars, freezing and shimmering in the atmosphere.

Essential lyric: Sometimes my hands // They don’t feel like my own // I need someone to love // I need someone to hold

35

Topaz Jones, ‘Herringbone’

2021

WRITER(S): Alissia Benveniste, Jack Hallenback, Scott James, George David Brandon Jones

The first time I heard Topaz Jones’ “Herringbone” it reminded me of the first time I heard Frank Ocean’s solo music.  It was there in the way they both coupled cultural confidence with sensitive masculinity.  In the soulfully pitched vocals alongside croon-able choruses and effervescent rap flows.  But I’m not accusing Mr. Jones of being a copycat— rather a descendant, as we all are to our musical ancestors.  Jones understands the importance of lineage.  On the outro of other album single “Black Tame” Jones samples a matriarch discussing birth order, and here on “Herringbone” the entire conversation revolves around family gathering and dynamic. 

Essential lyric: I’ma hold you down while others’ll hold grudges // And we don’t gotta explain it to people that don’t love us // The blues is Mo’ Better // The food is mo’ butter

34

Caroline Rose, ‘Feel the Way I Want’

2020

WRITER(S): Caroline Rose

From March 6th, 2020’s (oof) under-promoted, under-toured, under-celebrated, self-produced opus Superstar.  Funny, empowering, and undeniably groovy like a cut off of the indie-fied Rhythm Nation 1814, it’s yet another example of Caroline Rose saying they can write any kind of song they fucking want.  Harkening back to the rhythms and sounds of legendary writing/producing team Jam & Lewis, even consistently highlighting a cousin in the Ensoniq synthesizer family (Jam & Lewis used an Ensoniq Mirage on most of Jackson’s hits from Control and Rhythm Nation, whereas Rose employed the Ensoniq SD-1), “Feel the Way I Want” is a braggadocious embrace of self-love.  “I made the narrative relationship based, but you don’t really know what the relationship is,” said Rose.  “They are the embodiment of anyone who has ever doubted me and I’m like, ‘Give me my damn crown.’  It’s years of little comments that people make about not thinking that I am good enough.  I’m also paying homage to my past self that didn’t believe in me either.  That energy that I was putting out into the world of ‘I’m not good enough’ or ‘I’m not knowledgeable enough’ or ‘I’m not capable enough.’  People make so many excuses not to do something.  At some point, I had had enough.  I had enough of people disappointing me.  I had enough of feeling like I needed training wheels.”

Essential lyric: Everybody’s so quick to cry out and say // “You gotta keep your shit together” // But, baby, watch me freak out

33

Regina Spektor, ‘Laughing With’

2009

WRITER(S): Regina Spektor

“There are no atheists in foxholes” so the old saying goes, but Regina Spektor noticed you might not often find them in a few other contexts.  Spektor has always marched to the beat of her own drum, or piano stool, as is the case on “Poor Little Rich Boy” from Soviet Kitsch.  Here on “Laughing With” from Spektor’s fifth full-length Far, she asks the listener to contemplate all the many times we’ve leaned, maybe undesirably, on faith.  In the final hour, who amongst us will feel comfortable embracing the void?

Essential lyric: No one laughs at God // when the cops knock on their door // and say “we got some bad news, sir” // No one’s laughing at God // when there’s a famine, a fire, or a flood

32

Randy Newman, ‘Harps and Angels’

2008

WRITER(S): Randy Newman

In this song an older man gets sick, falls, and has a near-death experience.  So why is it so fun?!?  Maintaining his lifelong lyrical trend of winking to the audience and poking fun at everything including himself, “Harps and Angels” is classic Newman.  Amusing, tender, and arranged like a junkyard Baptist sermon (choir and all), you will undoubtedly find yourself chuckling at the delightful absurdity of life.  

Essential lyric: You ain’t been a good man // You ain’t been a bad man // But you been pretty bad

31

Phoebe Bridgers, ‘Motion Sickness’

2018

WRITER(S): Phoebe Bridgers, Marshall Vore

Riding in like an emo desperado on a Razor scooter, “Motion Sickness” was most listeners’ introduction to powerhouse feelings-excavator Phoebe Bridgers.  One of the best bummer bops ever laid down, it’s an immaculate recording.  Muted, fuzzed out guitar licks and a snappy snare alongside some of the most incisive lines in Bridgers’ catalogue.  And all the best songwriters know: a final chorus lyric change-up is money.

Essential lyric: You said when you met me // you were bored // And you // you were in band when I was born

30

Hop Along, ‘Sally II’

2018

WRITER(S): Frances Quinlan

“Two days gone: somebody checked in on you— that unsettling smell got into all the tenants’ rooms.”  This is how “Sally II” begins, and its tragic potency only grows exponentially from there.  A country punk song powerfully delivered by the incomparable Frances Quinlan.  Amidst vivid scene-setting and a woeful tale about mental illness, Frances drags us face to face with the reality of our mercy at our own minds.  

Essential lyric: Voices you were hearing, baby blue // Was it God? // Why did he only want to talk to you?

29

SZA, ‘Garden’

2017

WRITER(S): Craig Balmoris, Sergiu Adrian Gherman, Tyler Reese Melenbacher, Solana Rowe, Daniel Tannenbaum

Control is a phenomenal album.  It created a phenomenon in SZA, after all.  Across its myriad highs and vocal riffs, “Garden” sits like a gem at its emotional center, just as SZA appears like a pearl on a black sand beach in its music video shot on Maui (directed by Karena Evans and featuring a majestic cameo from SZA’s own mother and Control narrator Audrey Rowe).  Over stuttering drums and a percolating synth line SZA calls out personal insecurities and the inequalities of affection in a relationship.  Me personally?  I would bend over backwards for SZA, but now this writer is letting his own feelings bleed through…

Essential lyric: You know I’m sensitive ‘bout having’ no booty // havin’ nobody, only you, buddy // Can you hold me when nobody’s around us?

28

Portugal. The Man, ‘Purple Yellow Red and Blue’

2013

WRITER(S): Brian Burton, Zachary Carothers, John Gourley, Kyle O’Quin

I’m aware of the success of “Feel It Still.”  If this list were based on commercial success it would be mostly filled with a bunch of bullshit.  For several years Portugal. The Man made and released grimy, psych-leaning, indie prog, up through their 2011 album In the Mountain in the Cloud, of which frontman John Gourley told The Aquarian that year, “This record is the closest to what we create in band practice or in the live setting.  It sounds the most like us.”  But it was on 2013’s Evil Friends, produced by Brian “Danger Mouse” Burton that the band settled into a fresh, decidedly darker, black and neon color palate that they’ve continued to explore variations of since.  It’s kind of like a doom-y SoHo House vibe.  Intended to be a self-produced outing, Burton came on board mid-process after a fortuitous phone call and subsequent meeting that left everyone brimming with enthusiasm.  Gourley told PDX Monthly in 2013, “There would be times in the studio where Brian would turn around to me and say, ‘Man, I cannot believe your band.’”  You can hear the subtle flexing on Zach Carothers’ bass fill leading into the choruses.  Like a seedy Coachella banger (featuring pre-stardom Danielle and Este Haim on backing vox!), you could blissfully roll Molly to this song until potentially keying in on the lyrics and wondering if the lines “All that I needed // was something to believe in” could actually be applicable to you.  

Essential lyric: I don’t focus on the hopeless // When I look out // it’s only for me // All I wanna do is // live in ecstasy

27

The Chicks, ‘Not Ready to Make Nice’

2006

WRITER(S): Martie Maguire, Natalie Maines, Emily Robison, Dan Wilson

The story behind the song is almost as big as the song itself.  If you were of age to be engaged in politics, aware of pop culture, or a The (then Dixie) Chicks fan in 2003, you know that at a show in London, England lead singer Natalie Maines made clear her opposition to the impending invasion of Iraq saying, “Just so you know, we're on the good side with y'all.  We do not want this war, this violence, and we're ashamed that the President of the United States is from Texas,” referring to George W. Bush.  The resulting backlash across a primarily right-wing country radio listenership was almost immediate.  The Chicks were blacklisted from play on several outlets, and many listeners began to throw out or destroy their albums, some extremists going so far as to send the band death threats.  Produced by none other than sounding board/guru/business mogul Rick Rubin, whose musically direct approach lays a clear track for The Chicks’ declarative train to mightily roll in on, “Not Ready to Make Nice” marked a seismic autobiographical turn in the band’s songwriting.

Essential lyric: I made my bed and I sleep like a baby // with no regrets and I don’t mind sayin’ // It’s a sad, sad story when a mother will teach her // daughter that she ought to hate a perfect stranger

26

The Shins, ‘Simple Song’

2012

WRITER(S): James Mercer

James Mercer can write a solid, stunningly melodic song about anything, and he’s chosen to populate his songs with dense lyrics and many heady subject matters over the 18 years since The Shins inception in 1996.  On “Simple Song” Mercer, well, he simplifies things a bit.  A gorgeous song of courtship with lyrics so sincere you might blush as you relive a young romance in your head while the lines play out.  Drum fills like rolling waves amidst swelling guitars and swoon-worthy melodic turns, this is the stuff classic pop dreams are made of.  Written about “really building the nest” with his wife, Mercer remarked of the tune, “I’ve gained a lot of confidence, and a lot of it is because of my wife and the strength that she gives me.  That strength that you get from a real strong love.”  Also, his young daughters “love ‘Simple Song’…  If I started playing that, they would run into the room and spin around and dance…”

Essential lyric: I told you about all those fears // and away they did run // You sure must be strong // And you feel like an ocean // made warm by the sun

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Stay tuned for songs 25 to 1…