If you go, the bottomless cup runs out... The Jayhawks - Bottomless Cup
Tim O'Reagan is known as the drummer, backup vocalist and occasionally lead singer for the seminal Americana band The Jayhawks. He has also written and/or co-written many songs for the band including the fantastic Bottomless Cup featured below.
In 2005 he released a self-titled solo album. I discovered the album recently and I highly recommend it. O'Reagan's songs are very melodic and Americana sounding. His voice reminds you of a Lennon/Dylan combination. Some of the highlights for me include the opening tract These Things, River Bends, Just Like You, etc...
I got to see the Jayhawks in concert last year. They were fantastic.