The Emora Rav Ashi was once in the wealthy town of Mechoza for Shabbat. On Shabbat morning they gave him the honor to make ‘Kiddush Rabah’ for them. Rav Ashi quickly thought to himself what could they possibly mean by Kiddush Rabah? He figured all of the blessings start with a Bracha of Boreh Pri Hagefen so this must be a good way to start. After saying this Bracha he saw an elderly gentleman drink his wine so he knew that he had done the right thing and was now finished. (Pesachim 106a)
On the evening of Shabbat we make Kiddush over a glass of wine accompanied by an additional Bracha – blessing. During the morning Kiddush one needs to only say the bracha over the glass of wine as Kiddush. This is called “Kiddush Rabah – The great Kiddush” even though it is very succinct.
It is stated in the Ten Commandments “Remember the day of Shabbat” (Shemot 20 – 8) Our Rabbis of Blessed Memory stated that this teaches us to remember the day over a glass of wine. (Pesachim 106a)
The Meiri in his discussion on this Gemarah states that the day is sanctified and made memorable through having a special meal with wine.
Wine is so special that its presence at an event makes the event memorable. This is why Our Rabbis of Blessed Memory assigned a special Bracha – Blessing or “Boreh Peri Hagefen – He who creates the fruit of the Vine”
The Grape vine originally comes from the Middle East. From there it spread to the Mediterranean base and to the rest of the world.
The Tana”ch states several times that wine is memorable. Indeed it is often used as the analogy used to state that something is memorable. (Midrash Tanaim 5 –12 as well as Tosafot Pesachim 106a)
In Shir Hashirim the beloved is to be brought to the kings chamber. This memorable event is easier to remember than wine. (Shir Hashirim 1 – 4)
Hoshea states “they will be remembered like wine of Lebanon.” (14-8) This Pasuk refers to a day when the Jewish people will be looked up to. Therefore it really means that the people of Israel will be remembered like fine wine. (This is read as the Haftara for Shabbat Shuva)
Not all wines are equal. Rada”k on this pasuk cites the ancient book of Assaf the Physician. He discusses the wines of Lebanon, Hermon, Carmel, The Mountains of Israel, and Jerusalem, Shomron and of the Egyptian Kaftor Mountains. These are the finest wines in bouquet, flavor and even for healing.
A glass of wine is usually present at Jewish Ceremonies. In addition to Kiddush said on Shabbat and Holidays, during the Havdalah Ceremonies, A glasss of wine is often present during the Blessing of Birkat Hamazon after meals and of course at wedding ceremonies and the blessings said during the week of marriage.
Four cups of wine is required at the Passover Seder to give us a feeling of freedom and an unknown amount for Purim.
Additionally, some of Our Rabbis of Blessed Memory have required a mourner to drink ten cups of wine in order to drown his misery. Others require fourteen cups to be drunk by a mourner. Interestingly enough the fourteenth cup is in memory of the great Tana Raban Gamliel.
Before Raban Gamliel Jews were accustomed to spend their life’s savings and to go into debt to purchase an expensive sarcophagus and fancy funeral. The people started to escape out of town and would leave the deceased. Raban Gamliel commanded that his funeral be simple and that his body be wrapped in simple Linen. Since then that is the Jewish custom. It is certainly proper to drink a Lechayim toast in memory of Raban Gamliel (Ketubot 8b)
However, many Early Rabbis – Rishonim have stated that even ten cups is not required and a mourner should only drink during the meal as much as he needs.
An interesting broad view of wine and drinking is encouraged by Our Rabbis of Blessed Memory. Wine is almost always present in Jewish events. However, drunkardness is always discouraged.