Here is a set list I used over and over again to get my eldest to sleep when she was a baby. I was in grad school at the time, so if these didn't work, I read Managerial Accounting, Statistics Applied To Quality Assurance, or International Economics, and that would generally work.
Sweet Baby James (The Cowboy Song according to my kids) - James Taylor
Jacques Cousteau - Livingston Taylor
Featherbed - John McCutcheon
Crazy - Willie Nelson
Grandma's Featherbed - John Denver
Morning Has Broken - Cat Stevens
Slip Sliding Away - Paul Simon
Amazing Grace - Willie style version
King of the Road - Roger Miller
Age - Jim Croce
Big Wheel - Jim Croce
They Don't Dance Like Carmen No More - Jimmy Buffett
I remember one time I was in Philadelphia on business. After business was concluded, it was too late to drive home so I got a hotel and decided to go for some live music. I found a bar on-line and took a cab over to it. It was on the second story and there was an old wooden staircase with wood paneled walls leading up to it. Great acoustics in the stairwell. Anyway, I called to sing my lullabies from the stairwell, and while I was singing Sweet Baby James a few attractive young gals came in. It looked like they had already had a few "curb beers" to warm up. They huddled around me and sang back-up for the lullaby. They sang for crap, but I didn't mind the huddling.
Granted B chord amnesty by King of the Mutants (Long live the king).
If it comes from the heart and you add a few beers... it'll be awesome! - Mekidsmom
When in doubt ... hats. - B.G. Dude