I used macOS Sierra 10.12.6. I DON'T USE HOMEBREW! I tried to download from Vimeo with youtube-dl and got this:

ERROR: Unable to download webpage: <urlopen error [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590)> (caused by URLError(SSLError(1, u'[SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590)'),))

It's because OpenSSL version supplied with macOS out of date. So I updated openssl like this:

$ curl -O https://www.openssl.org/source/openssl-1.1.1b.tar.gz

$ tar -zxvf openssl-1.1.1b.tar.gz
$ cd openssl-1.1.1b

$ ./config

$ make

$ sudo make install

After that, I check openssl version:

$ openssl version
OpenSSL 1.1.1b 26 Feb 2019

And check where is it:

$ which openssl

But error exists anyway. Then I check what version python used:

$ python -c 'import ssl; print(ssl.OPENSSL_VERSION)'
OpenSSL 0.9.8zh 14 Jan 2016

It's old out of date version!

Question: how can I tell the python (and other apps that may use openssl) use the new version?

p.s. the python version is:

$ python --version
Python 2.7.10

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