Australia is probably the most Western in all the countries discussed here.

IMHO, Bolivia and Jamaica aren't even half Western. Bolivia and Peru are composed of more than 50% Quechua (former Inca kingdom) and still speak Quechua. I don't see why a mainly native American country should be more Western than Turkey, which used to be part of Ancient Greece, then Rome and remained a Greek speaking country till the Turl took over government in 1453. Ethnically and historically, Turkey is as European as Greece, which is laid the basis for Western civilization (without Greece, no Europe, no modern world).

Jamaica is an English speaking country with a strong black majority (like most Caribean islands) with 76% African descent, 15% Afro-European descent, 4% European, 3% East Indian & Middle Eastern, 1% Afro-Chinese & Chinese. In comparison, South Africa is also English (and Afrikaans, which is Dutch) speaking, and has a very similar ethical composition : 77% black, 10% white, 8% mixed race, 2.5% of Indian or Asian descent.
So, logically, if one is Western the other is too. Just being a part of the American continent doesn't necessarily qualify for Westerness.

Russia has always been a Western country till the 1917 revolution, and even with the same ruling family as the rest of Europe. Russia as a country was actually founded by Swedish vikings. It's not because of 80 years of communism that it's lost its Westerness. Ethnically and culturally as Western as white Europeans or North Americans. Historically more Western than America. The term Western is strange when applied to Russia because of its Eastern geographical location.

Finally, Israel is very much Western in mentality and system, but ethnically and linguistically Semitic (be it Jews or Arabs), so not European, and thus not Western. But almost anybody considers Israel as a Western country, as most of its Jewish population originates from European countries or the US.

Singapore is more Westernized than Japan because it was founded by the British and English is still the official language.