We did gunmetal pocket-watches for the groomsmen, and silver for the FOB and FOB. They were great! We got them on theknot.com, and since your budget is larger, you could probably do the watches AND a small personal gift specific to the person.

The reason why people usually get the same gift for everyone is that it's a memento of the wedding. You can choose not to do this, but then you may have one groomsman wishing he got what the other got, or thinking you spent less money on him, or whatever. By giving everyone the same gift, they get something nice, there is no competition or jealousy, and everyone is happy!

If I were you, I would get the watches ($20 each, roughly. They go on sale often), a small gamestop or best buy gift certificate (like $20), a decent bottle of whiskey($40), and a sports hat (or jersey, or any type of paraphernalia, with the team each one likes, $20) FOR EACH GROOMSMAN! So they all get multiple items, all get things they like. Although for the 17 year old, you can't give him whiskey. Perhaps make his giftcard larger. (to frou frou- you would never give a giftcard to say a parent, aunt, or uncle, but to a 17 year old? I think that's not tacky at all.)

OR, instead of the sports stuff, get them all cufflinks. Baseball bat cufflinks (try ebay) for the sports fan, and perhaps irish knot (if he likes irish whiskey, get it?) cufflinks for the other.

EDIT:

cufflinks:

http://cgi.ebay.com/base-ball-baseball-sport-game-MLB-world-series-cufflink-/350253591528?cmd=ViewItem&pt=LH_DefaultDomain_0&hash=item518cbdabe8#ht_997wt_656

http://cgi.ebay.com/Baltimore-Orioles-Cufflinks-/320420298950?cmd=ViewItem&pt=US_Baseball_Fan_Shop&hash=item4a9a89c0c6#ht_854wt_656

http://cgi.ebay.com/Celtic-Knot-Irish-symbol-new-Square-Cuff-Links-/320436080647?cmd=ViewItem&pt=LH_DefaultDomain_0&hash=item4a9b7a9007#ht_2092wt_656

http://cgi.ebay.com/Silver-Green-Celtic-Irish-Eternity-Knot-Cufflinks-/150454695111?cmd=ViewItem&pt=LH_DefaultDomain_0&hash=item2307cc74c7#ht_2617wt_944

Watches:

http://weddingshop.theknot.com/WEDDINGWAREHOUSE/ProductPage.aspx?pId=P2824(KnotShop)

Whiskey:

http://www.queenannewine.com/proddetail.php?prod=080432501177

http://www.bevmo.com/Shop/ProductDetail.aspx?

http://www.winechateau.com/vsku1000742_JOHN-JAMESON-IRISH-WHISKEY-80@-1.00L?utm_source=Google%20Products&utm_medium=feed&utm_campaign=JOHN%20JAMESON%20IRISH%20WHISKEY%2080@ProductID=3113