If the people are singing random devotional songs not connected with the sacrifice of the Mass - What, then, are they actually participating in?

COMMUNITY!!!

No, devotion.

I guess that's a bad thing now?

4) no appeal to modernity can nurture a love of the timeless;

1) to nurture a Catholic singing culture, one must sing Catholic music;

Happy-clappy parishes foster a sense of fear and distaste for the timeless chants of the Church. I encountered that last weekend... a musician who grew up in the rock and roll mass dismissed gregorian chant as "crazy" and "off". My opinion of that musician went strait down the drain. I'm sure we'll work together in the future, but I'll always know there is a certain disrespect of sacred music with that person, and it's just sad.

The problem is that we think congregational singing is the be all end all of parish music. Good music is defined as music everybody sings. If "they" don't sing it, its not good music.

A few quibbles....

Catholics DID have a culture of congregational singing... in some places (more than just a few cities in Austria).
The Holy Spirit did NOT reveal that we've been doing it wrong.
We are NOT supposed to sing like Baptists.

Ya gotta love the way Catholics sing on the Chartres pilgrimage.

The problem is that we think

Sorry, CK, but don't count me in the "we."

The problem is that we think

. . . I've found this to be true time and again. Far better not to think if all you want is equanimity and tranquility.

Adam:
With l due respect 1. Before Vat II: mass and singing is forbidden in the venacular, except in certain places where bishops allowed it mainly at adoration. 2. After V II: "the singing of the people is to be considered before all else" (Sing to the Lord)
My point it just that the church has no experience of this culturally and was expected to embrace a change in practice for which it was unprepared.
Perhaps I should have been more clear in my earlier post that by the term " singing culture" I meant singing by the people. Of course, Thank God historically there is a great culture of singing in the RC church, but not very much congregationally until recently, and hence the challenge.

ghmus7:
You are forgetting the preponderance of hymn singing at Low Mass (as well as devotionals, processions, and things like that), and also forgetting that "Sing to the Lord" (1) has nothing to do with Vatican II, (2) is a unique to the United States, and (3) is fairly recent, even relative to the Council.

Ok, perhaps lets go back to Adam's original question; what works for you?
Suggestions:
1. Strong organ leadership in supporting the congregation. Play rhythmically solid, at a singable tempo.
2. If possible solid choir and cantor leadership.
3. Develop frequently repeatable and easily sung repertoire for the people. Avoid tunes that are highly snycopated, and tunes that have different music for each verse. Each tune, whether an antiphon, hymn or whatever has to be clearly singable by the people.
4. People associate tune and text together. Avoid taking one tune and singing ten texts to it, this confuses people.
5. Avoid bizarre or embarassing texts that are theologically confusing.
6. Help clergy to model singing by holding and singing from a hymn book.

To be clear - you are talking about singing NOTHING CONGREGATIONAL, ONLY the proper, chanted by the schola, after which mass commences, with the congregation not uttering a word until the "Amen" after the sign of the cross?

In our suburban parish in the Pacific NW we do this, yes. Our schola slowly replaced the entrance hymn w/ the Introit over a period of several months. Here's how we did it:

(1) We kept the entrance hymn and added the proper just before it. We set the text (of the refrain only- at this point we left out the psalm verses) to a "chant-ish tune" that sounded like it fit w/ hymn we were about to sing. We (actually only one of us) sang that a capella, then the piano came in w/ the intro the hymn. The cross bearer did not to start processing until the "chant" was done and the hymn started (at which point, everyone stood up and sang like they were used to doing).

(2) During the same time period, we started chanting the Resp. Psalm. We got our music mostly from what's on Chabanel Psalms or Parish Book of Psalms and did this a capella. We felt this was the best place to introduce real chant (not the psuedo-chant we were using before the entrance ant.) b/c they were only repeating a short musical phrase after us, and they got to sing it several times so could feel good about having learned/participated by the end of the psalm. The point here was to (a) get people used to hearing modal music, (b) get people comfortable singing it w/ us. It's kind of a "trick" right? B/c people know they're expected to repeat the resp. psalm so getting them to sing chant w/ us was easy b/c they know this is their turn. In our parish, people were used to the paraphrased responsorial SONGS (you know- just another piece of music to fill the slot between the 2nd Reading and the Gospel). So when one of our schola members would cantor a capella from the ambo, I think it made it a lot clearer that the PIPs are supposed to respond in kind.

(3) After many, many months, we took out the entrance hymn. One weekend we announced before Mass started that we would be chanting an antiphon instead of singing a hymn. We told people it would feel very much like a Resp. Psalm, where a cantor would sing the refrain and people would repeat it, then a cantor would sing a verse, and we'd all come in on the refrain again. The cross bearer started the procession as soon as we started chanting.

(4) After more time passed, we added in the Comm. Ant. We didn't say anything about it, we just started doing it. People weren't shocked or confused, they just went ahead and did their thing (i.e., sing the refrain). We started out with only a few of the psalm verses but eventually started doing them all. We're such a large parish that we still get in 2-3 hymns after that.

(5) Finally, after more time passed (I'd say a total of a year at this point), we brought in the Offertory Ant. We also just started it w/out any "fanfare" (no announcement- just started doing it one week and haven't looked back). We do often still have time after the Ant. is over and will do a hymn after that.

So there you go. To be honest, we are overall a pretty P&W type parish and I was somewhat shocked that this worked! I will say there are three things that I am pretty sure have made a big difference in our success: (1) a VERY supportive pastor who, (2) SINGS the dialogues, and (3) a parish who was already singing heartily before we tried changing the direction of the music.

Congregational unaccompanied singing.

Get people used to the idea that the music won't happen without them, and they will rise to the challenge.

It should, in fairness, be noted that Adam works with Episcopalians. As a former Episcopalian, I know that small talk before dinner sometimes takes place in four-part harmony, from memory or improvisation.....

P.S. I think it also helps with chant Masses to have an antiphonal strategy. We have the ladies sing the first Kyrie and everyone joins in on the second and we keep alternating. The congregation then has a model to emulate and doesn't have to sing the entire time which might be helpful.

Also, speaking of chant Masses, I heartily recommend Mass V, Magnae Deus Potentiae. The Kyrie and Gloria have an irresistible rhythm. You just can't help but sing along (and you might even want to add a tambourine).

The biggest thing I can add as far as advice goes is:
Congregational unaccompanied singing.

YES! I think that makes a huge difference.

Toward that end, I really think that a great way to start (if you can) is to get the priest to chant the dialogues (of course a capella). The people know they *have* to respond w/ "And with your spirit" when Fr. says "The Lord be with you." If he chants it, the people will instinctively chant back. They *have* to- they almost can't help themselves even if they think they aren't singers or claim they don't sing.

Whether or not you've got a chanting priest, I do think any unaccompanied singing is a very good first step, and especially anything that's done antiphonally, as JulieCol mentioned.