Caricatures are a lot of fun and are a good option for a wine label, particularly for celebrations like weddings and birthdays. There are many talented caricature artists and several online services that provide caricatures based on supplied photographs.
Another group that should really think about using caricatures is realtors. Honestly, handing out bottles of custom labeled wine to your clients is a great idea. Don't spoil it by sticking your mug shot on the front of it!