In the time of Jesus, the Jewish community in Palestine had many factions. It's just not possible to think in terms of a single "Judaism" in the first century. Jesus, during his life, undoubtedly encountered various kinds of Jewish believers. Sadducees, Zealots, and Herodians are all mentioned in the Gospels, along with what the rabbis called ame ha- 'aretz (literally, "people of the land"). The latter were people from the lower strata of society who were unaware of ceremonial details; they provided many of the early followers of Jesus.
Historically, the most important group Jesus encountered was the Pharisees. They may have numbered only a few thousand, but they were tremendously influential. They were often associated with the "scribes," who were probably professional scholars in the Torah. Some of the most stinging rebukes Jesus issued were directed toward the Pharisees. Take a look at Matthew 23, for example. Throughout the chapter, Jesus declares: "Woe unto you, scribes and Pharisees, hypocrites!" He condemns what he sees as their greed, their hypocritical pretense of virtue, their focus on external minutiae, and their obliviousness to basic matters of justice, mercy, and faith. Such passages have given "Pharisaic" the meaning "hypocritical" (see almost any dictionary).
But Pharisaic Judaism was a highly idealistic and demanding tradition. The Sages who produced the classic works of rabbinic Judaism (the Mishnah and Talmud) drew directly from it. It produced the essential features of rabbinic Judaism, from ancient to modern times: the synagogue, prayer, Torah study, charitable giving, and so on.
We cannot dwell on the topic, because this is not a course on rabbinic Judaism. But those who would like to pursue the topic can consult http://www.fordham.edu/halsall/jewish/jewishsbook.html/ (click on "The Emergence of Judaism").