I mean, "Old" can mean Bob Wills and Hank Williams, Sr, or it can mean Cash and Jones and Cline, or it can be Dolly Loretta and Waylon and Willie, or it can be Kenny Rogers, or it can be the Young Country movement of the 90s, which produced some of the best acts country has ever had (Garth Brooks, Trisha Yearwood, Martina McBride, Patty Loveless, Dwight Yoakum, Chris Ledoux, Lyle Lovett, Mary-Chapin Carpenter, Alan Jackson, Clint Black...)
All of those eras also produced a lot of crap that no one remembers, so there's a filter effect going on.
COuntry goes through stages more than most other genres. They have periods of groundbreaking genius, then the executives realize profits are up and start hiring any hat-head they can find, and they saturate the market with formulaic crap, and everyone goes away, and eventually the suit guys stop hiring hat guys, and a new crop of talent is able to get a foot in the door, and it starts over.
Right now it's mostly mired in a dip, although there are some interesting acts out there. Rascal Flatts, Keith Urban (sometimes), Jack Ingram, and a few others are playing with the boundaries of country. None are brilliant, IMHO, though the Rascal Flatts singer has a hell of a voice, but at least there is something beyond the Brad Paisley crowd to hear.
I don't know if many from this era will become legends of Waylon and Willie status, though. The mid 80s were like that. The 2000s are like that. We're waiting on the next Outlaw, or the next Young Country, or whatever the next wave will be.
By the way, it was Waylon's birthday yesterday. For my money, he should have gotten all the fame that Johnny Cash got at the end. He had the interesting life (flipping a coin with the Big Bopper for the last seat on the Buddy Holly plane, for instance), the drug addiction, the longtime leather and lace romance (Stevie Nix claimed the song "leather and lace" was inspired by him and Jessie), the great voice (better than Johnny's but non-country fans don't realize that), and arguably a better guitar. Problem was, Waylon never got religion. He accused Johnny of selling out to religion, and he never, as far as I can tell, recorded a gospel song. The only religious imagery in his lyrics were negative, usually about human frailty and ironic religious references, like "Broken Promiseland." I loved Cash, and I'm glad one of them got the attention. I just think Waylon should have gotten some love.
Just for the fun of it:
http://www.youtube.com/watch?v=hnEtRUcKGwc (There's some mad greatness on that stage.)