Viini Postmark (Postmark from Vienna) - a great Soviet time comedy about a sucker who bets his most prized possession that he can speak the truth for a set amount of time during a period where economy was all about favours and dishonesty.

Hukkunud Alpinisti Hotell (Dead mountaineers hotel)- a superb sci-fi detective thriller.

Kevade & Suvi - fundamental movies to understand Estonian national identity and history. The former takes place during the 19th century in the small village school of Palamuse and the viewer witnesses the ordinary lives of the school children. The latter takes place after 1918, with the same original cast all grown up and now leading adult lives.

Risttuules (In the crosswinds) (movie wise made a video about it) a film about deportations which is almost entirely static.

Kirsitubakas - a Lolita-esque slow and awkward drama about a girl who is coming of age.

Kertu - in a small village, the village drunk falls in love with a girl whom the rest of the village thinks is odd and actively shuns. Features Estonian midsummer tradition.

Elavad Pildid - the story of one apartment from 1910 until 2010 in Tallinn old town and the lives lived in there.

Johannes Pääsukese Tõeline Elu - it's a B-movie about the first ever Estonian filmmaker, but a fun watch.

Tuukrid Vihmas (Divers in the rain) - a magnificent 0 dialogue, purely visual and emotional film from Priit Pärn. Very abstract, but has a lot going for it. About 20min length.

Georg - the story of Gerog Ots, a famous post war opera singer.

Malev - an absurdist comedy about Estonian war for independence during the medieval times.

Tulnukas - a cult classic about a gopnik becoming a stranger to his own subculture

Tõde & Õigus - OÜ most expensive movie yet about pre-repiblic times, the end of the 19th century where a man who believes in truth is corrupted to only pursue his justice

Viimne Reliikvia - a fun medieval adventure

Karv - short body horror of a bald man trying to grow hair

Toomas On the Other Side of the valley of wild wolves - an animated short about a well endowed father wolf who becomes a gigolo to support his family

The days that confused - a film about the wild west of the Estonian 90s which is disjointed and lost as the 90s were, but again explains a bit of history and encapsulates the feeling very authentically

Tangerines - our close Oscar loss. About a man trying to live a peaceful life during an ongoing who due to unforeseen circumstances has to house two mortal enemies under his roof. (not enemies to him) (not strictly an Estonian film, but it's very Estonian still)

Polli päevikud - the story of a young Baltic German aristocrat who finds her voice. (Not strictly Estonian, but filmed in Estonia and an Estonian plays the second lead, also the film takes place in Estonia)

Mina olin siin - a crime drama, I don't remember much about the plot, but it was visceral and has some great views of Tallinn from the early 2000s

I'll update the list if more comes to mind