If you can describe the show in one word it would
> "To protect the love I couldn't protect in my past life. To meet again in a liberated homeland and love freely."

The show is enchanting with Love , Friendship and Betrayal and it connects with viewers emotionally thanks to the excellent cast.

Cast
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Ji Soo Wan and KIm Cheol - We should really appreciate the writer and director for giving us this exciting plot that keeps us on toes till the end emotionally
[spoiler]
Yoo Ah In was excellent in his roles and subtle differences he produces between past [A Liberation Leader who gave upon on Love for the Nation ] and present character [ A Successful writer who abandoned multiple times deprived of love and betrayed many times to ever trust another person and living like a ghost]
Im Soo Jung looks like a Noona/Oba-san when she was supposed to be atleast 10 years younger but she has played both roles perfectly well past [ A Liberation Sniper ] and present [ A fan girl ; stalker ; who also has abandoment issues but saved by the Novels of Mr.Han ]
Kyoung-Po both roles are similar as they should be and I don't want to spoil much on him
Si-yang has crawled under my skin everytime he appeared as Baek Tae-min ; a pathetic
[/spoiler]

Story
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When I think of Chicago Typewriter, the first thing that comes to my mind is a Matryoshka doll. It might look plain at first sight but if you look closer, you spot all its beautiful details. While slowly uncovering layer by layer, your curiosity starts to grow because you want to know how much more there is to find. Until it takes you to a point where you eagerly wait for the next revelation that you know will come and in the end when you reach its final piece, you start to really appreciate every single item. Although each of them has their own shape and characteristics, you notice that special bond that connects every part, smoothly like a cogwheel. And when you put it back together afterwards, it matches perfectly again.

That's how I experienced Chicago Typewriter. I was sold from the first minute. The start was slow and the show takes its time to tell its story. But I never even once complained about the pace. I enjoyed every second of it. Why? Because I simply savored every interaction with the characters. It felt like they took me along on their journey.

The story, for me, sums up into a beautiful story about destiny and camaraderie that surpasses the boundary of time. Instead of being something completely new, it surely makes a lot of new choices in characteristics, settings and storyline.

The OST and Background music is excellent and it sucks the viewers into the show emotionally.

Experience
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I have put it off for long time seeing the premise thinking its a thriller and the middle part of series will be boring to binge ; but I was surprised to see how well it was directed and written . At times i have skipped few scenes because i couldn't wait in excitement but every scene is emotional so I would suggest to see it over a weekend or Binge for a rich experience.

I usually am not crying type unless it involves a real tragedy in the past and it would only last a scene but this show i had cried for last two episodes involuntarily. This show gets a 9/10 for the way it ended beautifully and the impact it had on me when it finished .

Overall, I really did enjoy this show. I would give it a solid 8.5/10.

The acting was superb from the three main leads, especially Yoo Ah-in, who managed to portray his present and past self in ways that were distinctly different enough for the viewer to distinguish them emotionally and mourn for each of their struggles in turn.
Go Kyung-pyo was equally as sympathetic as Yoo Jin-Oh. [spoiler] I did cry over him the most, as Yul, despite understanding why and how his decisions in the end were made. [/spoiler]

Im Soo-jung and Kwak Si-yang, as Jeon Seol and Tae-Min, I was less enamored with. Perhaps it was the writing, but they were just not as strong of characters [spoiler] especially in comparison to their past selves.[/spoiler] Additionally, a lot of the supporting characters around the main trio were just not that interesting or emotionally compelling. [spoiler] We never got emotional closure on the issue of Jeon Seol's mother, or Bang-Jin and 'Ricardo' one sided love for example. ( I think it would have been cute if they got together, but maybe I am in the minority.) And I never felt completely sold on Mr Baek Do-Ha's actual love and support for Se-Joo when his wife actually tried to commit legitimate violence against a child in her care...and his son was a spoiled sociopath and he really didn't do anything about it. [/spoiler]

The music for this show? Perfectly executed, very poignant. I also appreciated the costuming/tailoring, especially for the Joseon flashbacks.

I did get frustrated with the pacing in some places, twists were drawn out for too long and thereby lost their emotional impact. I had long figured out who-done-what before the big reveal.

Overall, I am glad I caught this on Netflix before being removed at the end of the month. It is still available on Viki though, and is worth the watch.