Pin Points and Gin Joints was produced by Ted Hutt, notable for working with other bands such as The Bouncing Souls, Flogging Molly, and The Gaslight Anthem.

The Bosstones announced that they were working on an album on November 4, 2008, via a MySpace blog with two songs, "The Impossible Dream" and "Next to Nothing" streaming on the page.

[8] Joe Gittleman described the band's approach to the album in an interview: "We really want to make a fun, upbeat record with a lot of cool ska stuff.

"[9] On October 19, 2009, the artwork for the album was posted online, and "Graffiti Worth Reading" was made available as a free download.

[10] On October 29, 2009, Pin Points and Gin Joints was announced for release in two months' time; alongside this, the track listing was posted online.