Playlist: Elliott Smith -Deep Cuts, Deeper Cuts, Deepest Cuts

By Tom Loughney ’16

When Elliott Smith passed away back in 2003, he left behind a gargantuan catalog of unreleased material that has since come to swim around in the ether of the internet. It’s an exciting time to be an Elliott Smith fan, in a way. Elliott may be gone, but his musical legacy has only expanded, thanks to the people who’ve uncovered and released nearly every recorded sound he ever produced. That being said, large amounts of content are a bit of a double edged sword. On one hand, there’s more media to consume. On the other, it can be kind of daunting to try and parse through hundreds of studio recordings and bootlegged live performances.

Don’t worry though. I gotchu.

My high school interest in Elliott Smith could have been described as religious. I spent hundreds of hours searching out every video, every recording, every little nugget of information about the God of singer-songwriters. I’ve since branched out, but – don’t worry – I’ve held on to all that good, good Smith-centric knowledge – and now I get to use it. This is the playlist I was born to write:  a guide to the best of Elliott Smith’s deep cuts – one that will ideally mitigate the difficulty of parsing his massive posthumous catalog, and further your interest and appreciation for one of the greatest songwriters of all time. I genuinely hope this playlist helps you discover and learn – I’m always looking for new people to talk about obscure Elliott Smith with.[1]

I’m getting way too sincere. Sorry, this happens when I talk about Elliott Smith. Old habits, I suppose. Leave a comment if you have any questions for me about the songs. As has – I’m sure – become clear, I can’t resist a good chat about some Elliott Smith.

Enjoy the playlist.

Dancing on the Highway

This was recorded during the Figure 8 sessions, but there just wasn’t enough room for it on the album – a real crime, as this is prime Elliott-experimenting-with-new-tech. He’d evidently just become familiar with looping devices, and effortlessly birthed this gem. I’m a particular fan of the sound and melody on the outro solo. You can also hear the ambient outro loop on Figure 8’s “In the Lost and Found,” and how it was really the base of this song. It is interesting to hear its sonic roots.

See You in Heaven


Most playlists like to end with this one, as it’s one of the last songs he recorded before he died. The lack of vocals also adds a little bit of mystery to the track, which is something people like about it, I think. It gives the song the potential for a positive interpretation – a possibility that many of Elliott’s songs lack. There’s actually a fan theory that this is a reworked version of another of Elliott’s songs – but I’ll get to that later. For now, enjoy this beautiful track – one that manages to be simultaneously upbeat and mournful. Classic Elliott.

A Living Will


A good transition out of “See You in Heaven.” This one’s got a similarly upbeat tempo, and highlights Elliott doing some fun, catchy stuff in his falsetto. “Leave well enough alone / Leave well enough alone.” It doesn’t seem like much at first, but if you sit down and really listen, you’ll hear just how much is going on in this track. I’m a huge fan of the bass. A pet peeve of mine is when bands never give the bassist anything to do, and just stick them with playing the bass note of every chord. This song is a pretty good example of how you can give the bass something fun to do without making the song sound too busy. It’s a very Beatles-y move of Elliott, but – then again – so is this song.

Suicide Machine


Ah, yes. This track. Supposedly the last song he recorded before he died – vocals specifically. I actually find this to be one of his most defiant, I-wanna-live sounding songs. Listen to the lyrics. “I’ll be riding forth on my pony / You’ll want to see me tonight / Dressed in black up at the line of attack / By my counterpoint in white.” This echoes a sentiment that Elliott expressed numerous times in interviews – people often pushed the “Mister Misery” label on him, even though he was more than just a sad person. “Everybody’s tryna turn me into a suicide machine.” Also, listen to those drums. This was recorded during the From a Basement on the Hill sessions, and if you listen to that album, it’s clear that the structural motif of those songs are dissonantly doubled instruments. The separate, intertwining drumlines that come out during the break/solo are, perhaps, one of the best examples of this technique across all of the Basement songs.

True Love


A recording artifact from some scrapped sessions Elliott had with Jon Brion. Friends of Elliott said that the song’s lyrics were initially about a love interest, but eventually changed into a song about drugs. Brion would evidently take Elliott and get him to work on this song with him to focus on non-drug activity. I think it may be Elliott’s most haunting song about drug use, mainly because of the way he conflates love and dependency. He and Brion had a falling out – likely due to a failed intervention – and Elliott abandoned all the recordings.



I feel conflicted about including this song on the playlist, but I think it’s an important song to hear if your appreciation of Smith extends deeper than his music. He actively suppressed this track during his lifetime, as it’s about the childhood abuse he suffered at the hands of his stepfather. It was released sometime after his death, despite his family’s protests. There’s really not much I can say about this track. Just listen, and feel your heart break into a million pieces.

The Enemy Is You


After “Abused,” I thought I’d include a little pick-me-up with this next song. I think this is the most positive Elliott Smith tune, hands-down. He’s talking about not getting inside your own head. Not becoming your own worst enemy. “Block it out / Well I know what I’m gonna do / With this big doubt / Gonna make it / Go away.” I’m a huge fan of the progression on this one as well. The emphasis on the acoustic guitar shows how the building blocks of Elliott’s forte – writing interesting, pop-y chord progressions – can hold up well, even without heavy arrangements. Fun fact: Carly Rae Jepsen’s “Run Away With Me,” off her recent album Emotion, uses a lot of similarly shaped chords.

No Confidence Man


Another song with an acoustic emphasis, but much moodier. This is an old recording made with Pete Krebs, a fellow Portland musician best known for his work with alt. band, Hazel. Hailing from the Roman Candle era, “No Confidence Man” has that rough, steely sound that many found so attractive about Smith’s solo debut. There’s also an excellent live performance showcasing a very, very blond Smith. He’s all about the bass tones on this one, and it goes well with the timid, high-register vocal harmonies he brings in at the end. Gives me chills, I tell you.

Where I Get It From


Now we’re going back even earlier. This is a recording from Elliott’s teenage years, I believe. Back when it was just him, a four-track, and a basement. I’ve included this because of how cool it is to take in the songs he wrote in his youth, and hear the country influences that shaped the fledgling style. The Hank Williams sort of folks were what he drew on, and you can hear that pretty clearly on this track. Also, he’s got a macabre, sardonic tone in his lyrics that cracks me up. “Great-grandad went mad, he was totally tweaked / He wore the same shirt every day of the week / And when I asked how it feels to be such a freak / And he said, ‘You tell me son’ / And that must be where I get it from.”

You Make It Seem Like Nothing/It’s Starting to Come to Me


Now we’re starting to transition out of rarities into more live performances. This is a blend of both – this is, quite possibly, Smith’s rarest tune – he only played it live a few times, and only two or three recordings of those performances exist. It’s also known as “It’s Starting to Come to Me,” in some circles. Not much to say about this one other than that. It’s not particularly impressive or anything, but I like it. It’s simple, short, and pretty. Enjoy.

Baby Britain (Alternate Version)


This is an alternate, finger-picked guitar arrangement of Baby Britain that he only played live. You can actually hear a brief rendition of this in the short film Lucky Three, of which Smith was the star. As far as I know, this is the highest-quality recording of this version. This comes from a performance at “End Sessions,” in L.A., if I remember correct. I included it more for its rarity that its quality, but also because it sounds so sweet.

I’m Doing Okay, Pretty Good/My New Freedom


Remember back at the beginning of this playlist, when I told you about a fan theory claiming that “See You in Heaven” is a reworked version of a previous song? Well here we are. Known as either “I’m Doing Okay, Pretty Good” or “My New Freedom,” this track is an absolute bummer. Talks about using alcohol to numb the heartbreak of a lost love, and faking stability. “You can go, and I’ll say what I should / I’m doing okay, pretty good.” Devastating. There are actually two versions that exist – the one above, and another version – one that eliminates the finger-picked playstyle. People believe this song became “See You in Heaven” because, when you mash them together, they fit oddly well. It wasn’t uncommon for Smith to recycle material, and I wouldn’t be surprised if this theory turned out to be true.

Waterloo Sunset


The Elliott Smith cover you probably recognize best is “Thirteen,” by Big Star – but one of my favorite off-the-beaten-path covers of his is “Waterloo Sunset,” by The Kinks. This is a fantastic performance from when he was still good friends with Jon Brion. It’s Elliott Smith singing The Kinks, man. How could I not throw this on the list?



This will be the first of two covers from Elliott’s Largo performance to make this list. Smith loved his Portland peers, and played this cover of Quasi’s “Clouds” during one of his best live performances of all time at Largo. A spirited acoustic rendition of a great 90s indie rock song. It’s damn near impossible not to groove a little bit to this one.



Holy. Shit. Can I say that? Am I allowed to write that? If not, just censor it out, editor.[2] Anyways – back to the song. The edge on those guitars. The energy in Smith’s voice. I never realized how great “Clementine” would sound as a rock song. I never even knew I’d want to hear a rock rendition of “Clementine.” Now I wish he had recorded this version in the studio. This is easily my favorite live performance of Smith’s – you can watch the full concert here, if you would like – and that’s largely due to how much this version of “Clementine” kicks ass.

All My Rowdy Friends Have Settled Down


I threw this cover on the list for two reasons.

  1. It’s a great cover of a one of Hank Williams Jr.’s more humorous songs, and – hopefully – this informs my discussion of Elliott’s country influences back at “Where I Get it From.”
  2. He’s having so much fun playing this song. I think this is the happiest I’ve ever heard him during a live performance – and I’ve listened to a lot of his live material. He’s laughing and joking with the crowd. He’s giggling during the song – getting goofy and enjoying it. You will never hear him laugh like this anywhere else, I promise you.

Unlucky Charm

Going in a bit of a different direction with this one. We’re back to live, original rarities, but this also starts to extend into a bit of a different tone. This is a performance from a set he played at Riviera, Chicago during the height of his drug abuse in 2002. This is his most infamous concert, mainly due to his inability to finish almost any of his songs. He’s pretty clearly high, and keeps talking about not being able to feel his hand. He makes it through this song – though not without some difficulty. Essentially, I’m trying to ease you guys into the next stop on this playlist. If you would like to listen to a cleaner recording that doesn’t have any mistakes, you can listen to that version here.

Poor Performances


Part of liking Elliott Smith is reconciling his drug problem with your love of him and his music. He wasn’t known for his great live performances – mainly because his dependency on alcohol and heroin usually got the better of him before shows. There are almost as many unfinished Elliott Smith performances as there are finished ones. It’s… really, really sad. This is a man I look up to. I’m sure that many of you look up to him as well. But it’s important to acknowledge his fallibility, and that’s why I’ve included this clip. This is one of his worst shows. It’s certainly his worst show that’s available on youtube. Here is a playlist of the entire set he played at Sunset Junction. It’s not pretty. It doesn’t sound good. But it’s who he was at the time. That’s why these performances – performances where he slurs his words, can’t remember the lyrics, can’t remember the chords – are important. This is the ugly side of Elliott Smith that people often forget – the side that didn’t fit the romanticized image of the tragically brilliant addict. He messed up. All the time. And you should watch it – to at least humanize him, if for no other reason.

Waltz No. 2 – Live Swedish TV


This comes from an interview he did that aired on Swedish TV. Turns out the Swedes really liked Elliott Smith. I really like this performance. It’s very tender, and he plays it a full step lower than normal – which is interesting, since “Waltz No. 2” is already played a full step lower than standard tuning. After bombarding you with his failures, I thought that I’d give you guys a breath of fresh air with one of Elliott’s best live performances of one of his most beloved tunes.

Misery Let Me Down


As far as anyone knows, this is the only recording of this song that exists – and he doesn’t even play the whole thing. He played this to warm up for a radio performance, and they just happened to have the tape running. A cool, catchy little ditty – I’m bummed we didn’t get to hear a finished studio rendition. So it goes with all our favorite deceased artists, unfortunately.

Son of Sam (Acoustic)


We’re rounding the final bend. Are you experiencing your kick? Have you stuck with me all this way? Have you read everything I’ve written? If so – I’m honest-to-god impressed. I accidentally wrote much more than I originally thought I would. Woops.

Anyhow, I’m closing out the playlist with two acoustic versions of two of the best songs off of Figure 8 – one of Smith’s best albums. Are you sensing a pattern? I don’t know what it is about this version. Maybe it’s the slight, tight reverb on the acoustic guitar. Maybe it’s the harmonica – it’s a very early-era-Elliott-Smith instrument to put on such a late-era song, which gives the song an interesting tone. It’s possible he always intended for a harmonica to fit somewhere on the song, as “Son of Sam” is actually a reworking of the the bridge on one of his high school songs, called “Shiva Opens Her Arms.” Regardless, the blend between old and new – Roman Candle instrumentation with a Figure 8 song – makes for an interesting rendition of one of Elliott’s greatest tunes.

Happiness (Acoustic)


The last track on this massive list, and maybe my favorite Elliott Smith song of all time. This acoustic version really highlights just how skilled Smith was at playing guitar. That opening is decidedly not easy to play, and he pulls it off perfectly – even and effortless. His voice stands out in some nice, roomy reverb as well – briefly escaping the haunted tenor that often characterized his vocals. Plus, you gotta love how this song ends. “What I used to be / Will pass away, and then you’ll see / That all I want now / Is happiness for you and me.” I dare you to listen to this and not smile a little bit.

That was it. That was my list, and a lot of my knowledge. Some housekeeping – for those interested in further exploring Smith’s near-hundreds of tracks worth of unreleased material:

  1. Here are some youtube channels that have a bunch of Elliott Smith’s unreleased songs. They’re nice people, and you should look at the stuff they’ve found.

  1. If you’re interested in the personal side of Elliott Smith, I would recommend reading his multiple biographies, as well as watching the extraordinary new documentary on Smith, Heaven Adores You. It has several unreleased songs on the soundtrack, as well as a bevy of information about his life and music.
  2. Finally, those interested in learning how to play any of Smith’s music, I would highly recommend looking at the site Smiling at Confusion. It has the most comprehensive – and accurate – collection of Elliott Smith tabs, period. Additionally, the official fan site has a page dedicated to fan-submitted tablature of his music.

I hope you enjoyed the playlist and the information. Have a good one.

[1] An occasionally Sisyphean task.

[2] S/O to the great, hardworking WKCO blog editors. They rule, and you should thank them for the hard work they do to make our word vomit readable.

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