Given that I sing 30-50 songs, 3, 4 or 5 times a week, this is a VERY hard thead to answer...

Off the top of my head... newest stuff fer me to be playing 'out'

We Are The Lonely - John Prine
Beer Run - Todd Snider
Girl From The Hiring Fair - The Garnet Rogers Cover (ish)
People My Age (Have Started Looking Gross) - John Gorka
$30.00 Room - Dave Alvin
Blue Wing - Tom Russel
Galway Girl - Steve Earle
Gladys Ridge - James Keelaghan
Next Time I'm In Town - Mark Knophler & Chet Atkins (A GREAT show-closer!)
The Ballad Of Hollis Brown - Bob Dylan


Most of which I suspect most people here don't even know...