Hasn't anyone mentioned Hank's THERE'S A TEAR IN MY BEER or Buck Owens' ACT NATURALLY? If you want something new, check out Brad Paisley's The Tin Man or THAT'S WHY I'M HERE. Of course, the best cryin' in yer beer songs are by Cajun musicians. But then again, you can't cry in your beer if you can't understand the words.
p.s. Don't exclude Hank's gospel songs. Sipping a quadruple Jack Daniels and Coke while listening to Lost Highway can have great therapeutic value on a lonely Sunday morning.