When Phil says he has a sailor in his mouth, is that a little wordplay, i.e., he has semen in his mouth?  Something about his delivery signaled that the line had another meaning to me.  It's the awkward kind of mood-killing mistake his character would make.

So for what it's worth, Wilco is a Chicago band, and the building on the cover of Yankee Hotel Foxtrot is Marina City, an iconic residential/commercial building on the river downtown.  As the show was set in Chicago, it seems kind of obvious why the character might have a copy of the album cover on his wall.

Or all-right in the case of Sedaris.