Ricky Skaggs' band is just plain awesome. He goes a little heavy on the Jesus talk, but musically, he's second to none.
I've never seen Patty Loveless, but her bluegrass album is quite good, and she aint bad to look at, either.
Saw Del McCoury at the Birchmere when he was doing the bluegrass tour with Steve Earle, and it was clear that Del was a bluegrass god, and Steve wasn't in the same league.
Don't know much about Riders in the Sky.
Saw Old Crow when I was out in SF, and though I wanted to like them, I didn't. Their singer puts on this over the top faux su-thun accent, and the band ends up sounding like the house band at the Americana theme park. Their fan base was very young as well, and ate their shit right up (aided no doubt by the smell of weed wafting through the crowd)