The Two Jews on Christmas (Again) session refers to a recording session that occured on 2002-12-25 which resulted in the recording of numerous songs which would go on to release on various singles, the LPs Soviet Kitsch, Begin to Hope, and Home, before and after, or not at all. The recording session was confirmed via a post Regina made reference on her personal website. On 2002-12-22, Regina posted, "i am wishing you all a wonderful new year, and a happy christmas... i am going to my 2nd annual "two jews on christmas session" with Joe Mendelson... see you choo-choo, reginka"

The songs currently associated with the Two Jews on Christmas (Again) session are only speculated, primarily due to many of the songs being included on the LP Soviet Kitsch only six months later. However, it is possible that some of these songs are actually associated wiith the Two Jews on Christmas session one year prior, as that session produced five unknown demos. Furthermore, it is possible that some or all of these demos are not actually associated with Two Jews on Christmas (Again) at all, but some other currently undocumented demo session. Regardless of their origin, how these demos ended up online is not currently known, though they were shared around the early Regina Spektor forums, brümstix, with many demos being available as early as 2003-07-12.