This is a fun thread, and got me thinkin'. I often listen to the old crooners and Bing Crosby is one of my absolute favorites. He has a lot of 'schmoozy' songs that I really dig, and many would fit here so I'll just pick two like "An apple for the teacher" and "Yes Indeed", love those, allthough they might be pretty standard for the era.

Im not really conscious about why I love those old songs, but it might be "Yes Indeed" for the combination of a great blues groove with a nice warm fun feeling in the vocals, and "An apple for the teacher" for the rythm and the vocal phrasing.