This past Shabbos, I attended a bar mitzvah where the boy’s 91-year old great-grandfather spoke. I nudged my sons to pay attention because the speaker, when quoting Hebrew, used an impeccable Lithuanian accent that is nearly extinct. Lithuanians pronounce the cholam vowel like “ay” (rather than “oh” or “oy”). It’s been years since I’ve heard phrases like “The Ribaynay shel Aylam” and “Tayreh”. Below is a synopsis and excerpt of R. Binyomin Shlomo Hamburger’s discussion of the subject. He is a partisan German-Jew but one of the few who openly discuss the variants within Ashkenazic tradition.
R. Binyomin Shlomo Hamburger, Shorshei Minhag Ashkenaz, pp. 21, 25, 27:
Four pronunciations of the cholam prevailed among Ashkenazi Jews in recent generations up to the time of the Holocaust: two in Eastern Europe and two in Western Europe. The table below illustrates these four pronunciations in both English and German as well as in the Ashkenazi pronunciation of Lashon HaKodesh.
Region of Diaspora Accent in Ashkenazi pronunciations Accent in German diacritic Accent in English Poland, Austria-Hungary komatz chirik – אָאִי Oi [t]oy Lithuania, Russia segol chirik – אֶאִי Aei [p]ay Northern Germany, Holland patach shuruk – אַאוּ Au [h]ow Southern Germany, Switzerland, France, Latvia, England, North America komatz shuruk – אָאוּ Ou [g]o …In Anglo-Saxon countries, the long “O” sound became the widespread pronunciation supported by the surrounding English language. After the Holocaust, however, many children and grandchildren of German Jews were subject to unwarranted ridicule for their pronunciation, and thus adopted one of the other pronunciations…
Those bnei Torah who were educated in today’s yeshivot do not conform to the Lithuanian cholam but to the Polish one. This comes to show that their choice of pronunciation is due not to an understanding of the subject, but merely the wish to follow their peers. They all chose the same yeshivish style which has become widespread only in this generation.

Moshe:
Yemenites preserved the greatest number of differentiations between sounds, but that doesn’t mean that they preserved Masoretic Hebrew as it was read 1000+ years ago. For instance, the Yemenite pronunciation of gimel-dageish as “j” (dzh) and quf as hard “g” is very unlikely to be original, especially since some South Arabian dialects of Arabic had a parallel shift of “g” to “j” and “q” to “g”.
Steg and Moshe,
Also, the yemenite vowels seems to be closer to babylonian than tiberian pronuciation.