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This is a great thread. That component of finding joy in Jewish ritual vs seeing it as dry legalism is, I think, one of the great misunderstandings between Judaism and (most of) Christianity. 1/x
And this isn't something that cropped up as Christianity & Judaism developed apart--it's there in the text of the New Testament.
The text itself positions Jewish law as something that's both burdensome and, in the end, impossible to follow. But the framing of the implied question there (is it possible to follow Jewish law to the letter without ever screwing up?) is...
...well, I'm reminded of the explanation of the Chinese word "mu" in Gödel, Escher, Bach (not sure if this IS actually what the word means, but I think the concept is important even if it's not an accurate representation of the word itself). 
And selling the idea that Jewish law is impossible to follow is a good strategy from an early-Christian marketing perspective. They're trying to market to a bunch of non-Jews who maybe admire elements of Judaism but are weirded out by not working one day a week or dietary laws.
And it's worth remembering that at the time, conversion to Judaism itself was relatively popular among Romans and surrounding cultures, as was worshipping with Jews without converting (people known in Judaism as "god-fearers"). So there was competition.
So the early Christian selling point is basically, "you get to claim this heritage and sense of chosenness and this deity and this promise of a better world to come, WITHOUT all that ritual and law you're ambivalent about."
So Jewish law and ritual gets painted as this INCREDIBLE BURDEN and impossible to achieve, sort of like those infomercials where brushing your hair turns into an incredible painful, snarled mess but don't worry, WE HAVE A BETTER BRUSH!
(It's sort of like selling apples and saying "New: OUR apples don't contain trans fat!!!")
And there's the implication (maybe it's stated directly, don't remember, been years) that if you screw up EVEN ONCE in following Jewish law, you're cut off from the divine (and probably go to hell). Which is, y'know, not how Judaism works.
Because what these early Christian writers were positioning as this enormous burden that Christianity could relieve, most Jews saw (and for practicing Jews, still see) as a gift.
And that doesn't mean it's not ever hard--take Shabbat as the most obvious example, in the most basic form of its practice. To say, no matter what happens (unless lives are at stake), one day a week, I'm not going to work at all is sometimes a challenge.
Jewish thought recognizes that, and also still sees it primarily as a gift, because it is, among other things, an assertion of freedom. We're not slaves: there are limits to how much of our lives work can have. Is it always easy? No, but freedom is sometimes difficult.
The whole idea of law, too, remains something that Judaism positions as a privilege, not a burden. To put the law into everyone's hands was a remarkably democratizing act then (and even now).
At the time, law was the province of kings. The Code of Hammurabi allowed for a commoner who accused another person to learn what the law about the act was, but not the accused.
To say to an entire people, "this code of law is yours--EVERYONE gets to know what it is and is responsible for upholding it," was, at the time, basically like saying, "you're all royalty."
And the extremism of "if you screw up even one little bit of this, that's it, you're done" is... not really a thing? Like, there's nothing in Judaism that says, "if you perform one mitzvah wrong, you're going to hell."
And, like, look, as with anything else, it's certainly POSSIBLE for Judaism to be legalistic--same as with anything else that has rules.
But the idea that it's some sort of arid legalism is basically an attack ad from 2000-years-ago Christianity.
But the idea that it's some sort of arid legalism is basically an attack ad from 2000-years-ago Christianity.
Or, perhaps it's more accurate to say, Judaism's legalistic in that it cares about law, but the idea that that's ALL it is or even primarily what it is, mindless adherence to custom, is not really in keeping with an evolving, multi-voiced, spiritually rich civilization.
And the idea that "do this thing which doesn't necessarily look spiritual in a particular way" is dry and legalistic is, like, so... do you do yoga as anything more than purely physical exercise? Or knit for any reason beyond "I require a piece of clothing"? Or...?
People follow all kinds of rituals. Treating the very idea of ritual as solely dry, arid, and hollow, rather than as practice that can be joyful, and the very idea of law as solely restrictive and punitive, rather than as protective and constructive...
...in the context of Judaism is playing into a nasty bit of competition from a world that's long gone. The mere fact that the Jewish people have survived 2000 years of diaspora intact is a pretty good indicator that there's a LOT more to that practice than unpleasant restriction.
