I read about this tradition a few years ago in my local newspaper and tried it. I've done it every year for about 3 years now and love to see the waitresses' reaction!
On Christmas Eve (or another night during the week of Christmas) we go out to look at all the Christmas lights around our neighborhood. All of the oooing and awwwing creates quite an appetite, so we stop at Sonic for a quick refreshment. When the waitress brings us our order, we give her a generous $20 tip and wish her a 'Merry Christmas'! One year this made the waitress cry and she told me she still had toys in lay-a-way at a store for her children. She wasn't sure how she would pay for the remainder of her bill. It made me feel so good to know that I had helped in some small way. And, I love the thought of helping someone who is willing to work on Christmas Eve!