Gordon Biersch is a good brewery/restaurant. Kind of formulaic, but good.
Same for Elephant Bar.
http://www.gordonbiersch.com/locations/san-jose-ca
http://www.elephantbar.com/

Really ritzy would be Alexander's Steakhouse.
http://www.alexanderssteakhouse.com/

A friend of mine swears by Little Lou's BBQ. I haven't been there yet, but had a bottle of sauce that was a hit at the ranch party.
http://www.littlelousbbq.com/

edit:
Gordon Biersch is just around the corner from a comedy club that's pretty good, too.
http://www.improv.com/
Not sure of the headliners for this weekend, though.