The album was recorded by John Congleton and arranged by Brian Beattie. In an interview with Uncut, Callahan described the recording of the album:
I recorded the basic tracks with a band, in August I think. Then gave the tracks to the arranger Brian Beattie to write some string and horn parts while I was on tour in South America and North America. When I got back we put the overdubs on, in an old fashioned way - four or five string players gathered around one microphone. The basic band is a couple fellers who I'd been touring with a bit lately, Jaime Zuverza on fine and pretty guitar - Brian described his playing style as "unmacho" which I thought was great. And Luis Martinez on special drums. The bassist was Bobby Weaver who was a friend of the engineer John Congleton. I could go on but this is supposed to be a short blurby interview, right?
Sometimes I Wish We Were an Eagle received very positive reviews from music critics and made several publications' year-end best album lists, notably being named the second best album of 2009 by Mojo magazine.
In 2013, NME listed the album at 443 in their list of the 500 greatest albums of all-time.