We will start with some history:
Sadly like a lot of cool things anamorphic lenses have a military background and were originally developed by Henri Chrétien during World War I in order for tanks to have a wider field of view.
In a way anamorphic lenses are a kind of wide angle converter. What makes them special though is they only compress one axis. This way you can build an optical system that is vertically a 50mm and horizontally a 25mm lens. They do this by using cylindrical lens elements.
I attached a picture of cylindrical and spherical lenses to this toot.
Cylindrical lenses focus light into a line, while spherical lenses focus light into a point.
Spherical lenses are typically used for normal photography lenses.
Back to history:
At some point in time movie theaters had to face a problem because there was something new in town - the television. Because of it less people went to see movies in cinema. Back in the day tvs and movies were mostly shot and shown in a 4:3 aspect ratio.
So in order to get people back into the theater something new had to be developed: Widescreen movies!
Anyway back to shooting. How can we get a wide screen image on a standard 35mm motion picture film?
Well using an anamorphic lens we can squeeze the horizontal axis giving us a compressed image which we can then by also using an anamorphic lens on the projector desqueeze to get a widescreen image.
Picture by https://en.wikipedia.org/wiki/User:Wapcaplet (CC BY-SA 3.0)
This is an anamorphic adapter for a 16mm film projector. You attach it in front of the normal spherical lens the projector has to desqueeze the anamorphic image back to normal.
As you can see - looking trough the front - the back looks like an oval shape even though it is round. When looking trough the back you also see an oval opening but it is wider instead of squeezed.
This can be quite annoying of course but thankfully you can also use a variable diopter for focusing!
What you do is basically set both spherical and anamorphic lens to infinity. And then add the diopter in front and use that for focusing.
They basically work like this: You have two diopters which cancel each other out when they touch (=infinity) and if you space them apart their strength increases focusing the whole system closer. I attached an image of a popular diopter for this.
This is how such a setup can look like assembled. You have a camera with a spherical lens attached and in front an anamorphic adapter lens. Add a variable diopter to the front and viola you have a usable setup where you only need to focus the front diopter instead of both lenses at the same time.
Focusing both lenses can be fine if you only shoot stills but for motion pictures it is not a usable solution.
This is the unedited picture I took. As you can see it is squeezed and looks pretty digital (because @lastfuture asked about the analoge look).
After that I used Photoshop to desqueeze it because there sadly is no way to do that in Lightroom which is really annoying 😭 Anyway the result is this https://whisper.tf/@paul/103374554458694312 :) I also tried to fix the overexposed light a bit in Photoshop.
In case you use a Canon camera, you can use the Open Source Firmware extension https://magiclantern.fm to get a desqueezed preview on the camera monitor which is very helpful 🎉
Most cameras designed to professionally shoot video have this feature built in. The only still / video hybrid camera that has it is the GH5 (and probably other Panasonic cams?) and I think the Sigma fp.
Some more things about the film like look:
A lot of modern lenses + modern cameras result in a very clean image because modern lenses tend to be overcorrected or optically too perfect.
On these images I used a Helios 44-2 (old Russian lens) which is of course far less perfect. It has a lot of highlight blooming creating a softer and more atmospheric image. I don’t really like it’s lens flares and it’s not the sharpest images but it has some nice aspects to it.
The anamorphic block in front also adds some more character to the image of course. First of all most anamorphic lenses tend to only really be sharp at the center and have some kind of focus fall off towards the edges (not all but most). They also make the bokeh (the out of focus parts of the image) oval instead of round.
In case you are using modern lenses but want to add some more character to your image filters can also be a very big help! They can diffuse your image / or parts of it and make it more pleasing to the eye.
For example this one: https://tiffen.com/products/black-pro-mist-filter
There is a great video from Tiffen comparing all their diffusion filters here: https://vimeo.com/92660033
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