Hi, everyone. I'm Wednes - here to present you with the amazing original soundtracks of drama Chicago Typewriter because I'm obsessed and writing this is another great way to procrastinate... * I translated every Korean song myself. Please kindly link back to this page if you wish to share. I will rearrange and add words to make the translation make sense in English. I don't translate them line-by-line. 
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Also, I don't think I can stop anyone from making an "ENG SUB" video of these songs, but please refrain from doing so because uploading music that's not yours to Youtube is illegal. You know it. But thank god to you people, most of the time you make it easy to find music to listen to... I'm a sinner. This thread was made on May 18, 2017. New songs that come out after that will be posted in comments below.
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Album Title: Chichago Typewriter OST Part 1
Artist: SALTNPAPER
Release: April 8, 2017
Lyrics: Nam Hyeseung, Park Sanghee, Jello Ann
Composition: Nam Hyeseung, Park Sanghee
Arrangement: Name Hyeseung, Park Sanghee
Copyright: CJ E&M Music
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Track 01: SALTNPAPER - Satellite (위성)
Track 02: SALTNPAPER - Satellite (위성) (Instrumental)
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I'm walking all night long in mysteries
You're singing all day long in maze
Without song in my heart, it is a lie
Still I am wondering why
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I'm feeling all my lights going out

All I can hear is your lullaby
From your guide now I'm here without knowing
Those melodies I sing like I know
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Don't wanna say goodbye

I wanna hear your voices in dreams
Don't wanna see your tears
I wanna see your traces
I hear you
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Say I will

If our tears haven't fade away
I may cross now or I won't
Say I will
If our hands didn't get to hold
Hourglass stories of me and you, we loved
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Satellite love
Through the rain, to the stars
Satellite love
Through the rain, to the stars
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Say I will

If our tears haven't fade away
I may cross now or I won't
Say I will
If our hands didn't get to hold
Hourglass stories of me and you someday
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Satellite love
Satellite love
Satellite love
Satellite love
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Lyrics Source:  Naver Music
* This song is originally in English.
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Album Title: Chichago Typewriter OST Part 2
Artist: Baek Yerin  
Release: April 15, 2017
Lyrics: Nam Hyeseung, Park Jinho, MIYO 
Composition: Nam Hyeseung, MIYO 
Arrangement: Name Hyeseung, MIYO 
Copyright: CJ E&M Music
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Track 01: Baek Yerin - Blooming Memories (아주 오래된 기억, lit. 'Very Old Memories' / 'Memories From Quite Long Ago')
Track 02: Baek Yerin - Blooming Memories (아주 오래된 기억, lit. 'Very Old Memories' / 'Memories From Quite Long Ago') (Instrumental)
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오늘 있지 나는 너에게
문득 느껴져, 아주 두려웠던 순간
그게 어떤 마음인지 
그리움 혹은 미움일까
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Today, I suddenly feel something towards you
It was quite a fearful moment
What kind of feeling could it be?
Was it longing or was it hatred?
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어떤 날엔 그런 날 있어 
무엇인지 모를 낯선
어떤 향기로부터 어떤 날엔 소리로부터 
아주 오래된 기억을 느껴
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There is that kind of day
that I can feel the very old memories
from the unfamiliar scents
from the sounds on some random day
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* Slowly Bloom In My Heart 
까마득했던 기억이 선명해져 갈 수록 
Love Bloom In My Heart 
알 수 없는 마음을 느껴
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As I go on, the memories that were so distant
slowly bloom in my heart
and become clearer
Love blooms in my heart
I feel emotions that I don't know
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손을 대면 느낄 수 있는 
이 저릿하게 아픈 이유는 뭔지
기억하고 싶어서 
자꾸 네게로 걷는 나 
한발 한발을 너를 따라서
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I follow you step-by-step
as I keep walking towards you
because I want to remember
what this numb and hurtful reason
I can feel whenever I touch is
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** Slowly Bloom In My Heart 
까마득했던 기억이 마침 눈을 뜬 순간 
I Run To Your Heart 
가장 아름답던 순간으로
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The once distant memories
slowly bloom in my heart
right at the moment I open my eyes
I run to your heart
to the most beautiful moment (in the past)
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어느 꿈에 
어디 인지 모를 그 공간 속을 헤매고 있을 때
내가 이렇게 아프고 자꾸 눈물 나던 그 모습이 
햇살에 비친다
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Whenever I'm wandering inside
some kind of dreams and space I cannot tell where,
that image of me who keep hurting and crying like this
shines with sunlight

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(**)
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My Everlasting Moment In Life
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Korean Lyrics:  Naver Music
English Translation:  [email protected]
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* continue in the comment below and the last album OST Part 5 is wayyyyy below and the 1939 song that Anastasia/Ryu Suhyun sings in episode 5 & 10 is below that – don't forget to scroll down!
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Album Title: Chichago Typewriter OST Part 3
Artist: SG Wannabe 
Release: April 22, 2017
Lyrics: Dona, Ricky, CuzD
Composition: Dona, Ricky, CuzD
Arrangement: Dona, Ricky, CuzD
Copyright: CJ E&M Music
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Track 01:  SG Wannabe - Writing Our Stories (우리 얘기를 쓰겠소, lit. 'I'll write our stories')
Track 02: SG Wannabe - Writing Our Stories (우리 얘기를 쓰겠소, lit. 'I'll write our stories') (Instrumental)
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여기 우리의 얘기를 쓰겠소
가끔 그대는 먼지를 털어 읽어주오
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I will write our stories here
Please dust it and read it sometimes
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어떤 말을 해야 울지 않겠소
어떤 말을 해도 그댈 울릴 테지만
수 많은 별을 헤는 밤이 지나면
부디 아프지 않길
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What words should I say so that you will not cry?
Although you will cry anyway,
please don't hurt anymore
after the night of counting countless stars passes
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* 여기 우리의 얘기를 쓰겠소
가끔 그대는 먼지를 털어 읽어주오
언젠가 사랑에 대해 묻는 이를 만난다면
전부 그대였다고 말하겠소
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I will write our stories here
Please dust it and read it sometimes
Someday when I meet someone who asks about my love,
I will say it was all you
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그대의 잘못이 아니오
비겁한 나의 욕심에 그댈 놓친 것이오
시간이 지나면
나를 원망하고 잘된 일이라 생각할 것이오
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It's not your fault
It's my cowardly greed that let you go
When time passes,
you will resent me and think that it was all for the best
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웃어주시오 이젠 돌아서겠소
다시 사랑할 수 있길 바라오
다만 아주 가끔 기억해주시오
서툴렀던 만큼 눈부시게 아름다웠던
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Please smile, I will go away now
I hope you can love again
However, please just sometimes
remember (our stories) that were as clumsy
as they were blindingly beautiful
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(*)
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Korean Lyrics: Naver Music
English Translation:  [email protected]
* This song is written in an old speech tone used to write letters back in the old days. It is as if the singer is reading his letter to his lover. So much fitting with the tone of the drama. I cannot get over this song and I will not. Damnnn...
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Album Title: Chichago Typewriter OST Part 4
Artist: Kevin Oh
Release: April 29, 2017
Lyrics: Kevin Oh
Composition: Katrine 'Neya' Klith, Daniel Davidsen, Peter Wallevik, Michelle Jo
Arrangement: Katrine 'Neya' Klith, Daniel Davidsen, Peter Wallevik, Michelle Jo
Copyright: CJ E&M Music
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Track 01: Kevin Oh - Be My Light 
Track 02: Kevin Oh - Be My Light (Instrumental)
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Look up at the stars that light the night sky.
Wherever you are, remember they shine.
Oh when the wind blows, I'm feeling you here.
Forever I'll know that forever you're near in my soul.
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This my prayer in darkness, don't let go of me.
Do you know where your heart is? It's where I want to be.
Without you here I'm falling. What else can I do?
Through the years I'm calling, I'm calling home to you.
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Be the one who says I want you evermore inside.
You're the only one who knows me.
Won't you be my light? Be my light. Be my light.
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Somewhere in our dreams, in our highest heights,
I'm there in between. I'm there in the light.
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This my prayer in darkness, don't let go of me.
Do you know where your heart is? It's where I want to be.
Without you here I'm falling. What else can I do?
Through the years I'm calling, I'm calling home to you.
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Be the one who says I want you evermore inside.
You're the only one who knows me.
Won't you be my light? Be my light. Be my light.
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Won't you be...
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Look up at the stars that light the night sky.
Wherever you are, remember they shine in your heart.
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Lyrics Source: Naver Music
* This song is originally in English.
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I love every single song in this drama. Thank you so much for translating it for us!!!
Next time plz write analysis & song translation for other dramas as well would be nice!! good work!
Thank you so much @WednesHwang This drama and OSTs mean a lot to me.
it'd be cool if u write romanized lyrics for us too but if not its ok :))
@Thevilone: Thank you for reading!
@soojungstrash: I will if I find a new addiction :D
@Gulsen: You're welcome :)
@immortalcupcake: Oh, it's okay. I will soon :)
im dropping by to wait for u to come back ^^ there are new release OSTs
I love Baek Yerin's song!
Good work!! All the songs are amazing. Thanks a lot.

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Album Title: Chichago Typewriter OST Part 5
Artist: Boni Pueri
Release: May 27, 2017
Lyrics: Nam
Composition: Nam Hyeseung, Park Sanghee
Arrangement: Name Hyeseung, Park Sanghee
Copyright: CJ E&M Music
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Track 01: Boni Pueri - Come With Me
Track 02: Boni Pueri - Time Walk
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Free your soul of the past
Love and the despair
Don't hold your breath
Close your eyes and dream
of long lost pale moonlight
In the endless sapphire sky
And I'm here tonight 
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Come here with me
in behind the shadow
Pass through the dark
it's a secret of night
Wait till the bluebirds
Till the bluebirds whisper
That you're a rainbow
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In softest air we fly
Now I'm here in your eyes
And a moment with you
Shines the light on my heart
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See me now I'm in your eyes
And stars see us through tonight
Fly now I'm with you
Stars see us through all the night
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Free your tears behind old days
Love and your despair
Now you're in my dream
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Let go all your lost wishful night
In sweet breeze we fly high
Now I'm here in your eyes
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Close your eyes and dream
In sweet breeze we fly high
Hold this moment we share
Now you're in my dream
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Close your eyes and dream
of long lost pale moonlight
in the endless sapphire sky
Shining on your smile
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Lyrics Source:  Naver Music
* This song is originally in English.
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Album Title: Chichago Typewriter OST Part 5
Artist: Boni Pueri
Release: May 27, 2017
Lyrics: Nam Hyeseung, Jello Ann
Composition: Nam Hyeseung, Park Sanghee 
Arrangement: Name Hyeseung, Park Sanghee
Copyright: CJ E&M Music
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Track 01: Boni Pueri - Come With Me
Track 02:  Boni Pueri - Time Walk
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Morning breeze blowing
my hair into single piece
Take me away
Thousand days flying by my side
All for us
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Morning rain walking
on shore waiting rainbow
Wait for it
If one day only if I can be
I'll hold you
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If I ever walk in time
We will together as one
All the happy times of ours
Shine the light thru gloomy night
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If sun set was beautiful enough
to share with you for all day
Oh moonlight light up the night enough
I can not see for all day.
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Time has gone I see you
Looking back to the good times
See you again flying tonight
Until the time none we can do
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All the happy times of ours
Shine the light thru gloomy night.
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Lyrics Source:  Naver Music
* This song is originally in English.
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Pls add the song from 1930

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Artist: Park Danma
Release: 1939
Lyrics: Lee Boopung
Composition: Jeon Surin 
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Track 01:   Park Danma - Nallari Baram 날라리 바람
* It's difficult to translate the title into a short title, but Nallari Baram at first glance describes wind that blows idly/slowly in one direction, thus it can also describe a person who wanders around without a destination. Because of this, "nallari" is also used in modern days as a slang term to call people (mostly men) who laze around, have no job, drink every day and flirt with girls without any serious intention. However, just keep in mind that this song was written in 1939 and only refers to the description in my first sentence.
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1. 마음 달뜬 새악시의 머리기름 냄새
가는 봄 끌어안고 슬피 우는 뻐꾹새
야리 야리 날라리
날라리 바람이 불어서 거미줄에 내 목을 메고
아이고나 데고나 나를 살려 주구려
나를 살려 주구려
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The smell of oil on the head of an excited new bride
The sound of cuckoos crying sadly at the end of Spring
Oh, the wind is blowing lazily
and spider's web is choking my neck
You'd better come save me
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2. 내 고향 생각할 때 달이 뜨던 저 고개
가는 님 마주 잡고 안달하던 산고개
야리 야리 날라리
날라리 바람이 불어서 거미줄에 내 목을 메고
아이고나 데고나 나를 살려 주구려
나를 살려 주구려 
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Whenever I think of my hometown
(I think of) That hill where the moon used to rise
That hill where I held onto that person who was leaving with my anxious heart
Oh, the wind is blowing lazily 
and spider's web is choking my neck

You'd better come save me
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3. 온다고 속여놓고 아니 오는 내 심사
어두운 그믐밤에 혼자 우는 내 심사
야리 야리 날라리
날라리 바람이 불어서 거미줄에 내 목을 메고
아이고나 데고나 나를 살려 주구려
나를 살려 주구려 
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I was fooled that (he) will come back,
No, I was sure that (he) would come back,
My reflection was crying alone in the dark night of new moon
Oh, the wind is blowing lazily
and spider's web is choking my neck
You'd better come save me
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Korean Lyrics: Gasazip (but I edited some words since they were misspelled)
English Translation:  [email protected]
it looks like a difficult song or my English is very bad
is it a song or a poetry?? if i may ask?