If you see a Van Winkle -- any Van Winkle -- consider it a premium bottle. Don't overlook Jim Beam Black-label for a value bourbon (but, please, steer clear of the white-label offerings). W.L. Weller 12yo is another great bottling that's easy on the wallet.
- Buffalo Trace
- Eagle Rare Single Barrel
- Elmer T. Lee Single Barrel
- George T. Stagg, Eagle Rare 17 (parts of BT's Antique Collection), if you can find them
- Evan Williams Single Barrel (any 'vintage' -- distilling year is listed on the label)
- Old Forester Birthday Bourbon
Not a single one of the bottlings I've listed will top $50 (well, the Pappy Van Winkles, if you find any, will and the Antiques approach it). Many can be had under $30.
LeNell's in Red Hook (Brooklyn, I think -- barely on Long Island, I realize) has as varied a selection of bourbons as can be found in the NYC area.