I think there are a few ways to pair Osso Bucco.
1) The most classic pairing is a Barolo or Barbaresco (the two great red wines of Piedmont). If you get one of these you will probably need to open the wine in the morning to drink with dinner, unless you find a good '96 laying around somewhere -- you'd still need to open that a few hours before dinner. The producer's you should be on the lookout for are
-Silvio Grasso (Barolo Bricco Luciani)
-Cavalloto (any Barolo)
-Pira (any Barolo)
-ALBINO Rocca (any, particularly Barbaresco Brich Ronchi)
-La Spinetta (any, particularly the Nebbiolo/Cab blend called "Pin" which is a Piedmont but not a Barolo or Barbaresco -- also this does not nd to air for more than 3 or 4 hours)
-Luciano Sandrone (my favorite Piedmont producer-- very pricey Barolos -- $110 -- but delicious. Also makes a $35 Nebbiolo and a $30 Barbera that would work)
All of the wines I have listed should range from $45 through $110, depending on which one you get. Also, you should make every effort to get a 1997, and if that is impossible, a 1998. For La Spinetta, 1999 is also ok. If you get a '98 you really do need to let the wine breathe for at least 6 hours before drinking it.
HOWEVER, even though Piedmont is the most classic pairing, I'm not convinced it is the best.
I would go with a Rhone: either a great Chateauneuf-du-Pape or a Cote Rotie.
1998, 1999, 2000, and 2001 are all great years for CdP and virtually all CdP's are in your price range. Here are my suggestions for more immediately appealing CdPs:
-Bousquet des Papes "Chante Le Merle"
-Domaine de Marcoux
-Le Callioux (sp?)
If you wanted a Cote-Rotie (more floral with a real burnt quality to it, sometimes can have an olive taste and have a reisiny-pot-like smell, but in a great way) I would seek out one of the following:
1998 B. Levet
1997 Jaboulet Jumelles
any 1999 from Rostang, Ogier, or Tardieu-Laurent.
The Chateauneufs mentioned range in prince from $25 to $45, the Cote-Roties range from $45 to $125.
As far as Amarone is concerened, I love the stuff but depending on which Amarone and your exact recipie (I base my recipie on Marcella Hazan), I feel an Amarone might overpower the dish. If you want an Amarone, your best bet is Tomasso Bussola BG which should be in the neighborhood of $50. Better, but more expensive is his TB which is around $85. Any vintage of these wines is fine, but open the wine a few hours before drinking. [1995 Dal Forno and Quinterelli are very hard to find and super-expensive (Quinterelli is almost $200, Dal Forno a little bit less) and the need an entire day of air, but they are amazing wines]. 1995 Zenato ($50) or any recent vintage of Allegrini ('95-'98) ($70) should work. Again, I'm not absolutely in love with the idea of Amarone, but it certainly would work and these are all magnificent wines.
One other thought: Cult Zin and rich CA Pinot Noir would both be very interesting choices.
Any Zin made by Turley or Martinelli in 1999 or 2001 would be great. Depending on gouging and vinyard, these wines can cost betwen $30 and $150 for Martinelli Jackass Hill. Most are under $100.
A Big CA Pinot Noir such as those coming from the Pisoni Vinyard in the Santa Lucia Highlands would also be interesting, the best producers in that vinyard are Peter Michael, Ojai, and Siduri. The wines run $55-$70. Also a Martinelli Pinot Noir could work.
I would serve a Rhone unless I, or a guest, was in the mood for something else -- or I wanted to be traditional in my pairing. If I did serve something else, my pecking order would be Piedmont, then big Cali Pinot, then Big Cali Zin, then Amarone or Tuscan wine such as a 1997 Brunello di Montalcino from just about any producer.
My diatribe is finished, I hope some of this is useful.