Live in Japan captures Jack's band in its original trio form, with Bassist Merlo Podlewski and drummer Adam Topol touring Japan in front of rapt Japanese audiences performing selections from Brushfire Fairytales and On and On as well as an early version of “Banana Pancakes” which appears on In Between Dreams. Donavon Frankenreiter and Money Mark make guest appearances.

Shortly after the completion of the Japanese tour, the band convened in Hawaii to record his new album In Between Dreams, with Zach Gill from Animal Liberation Orchestra adding piano and accordion. A Weekend at The Greek captures the band's expanded sound and 4 piece lineup ( Gill joined as a touring member of the band) as well as sit ins from the growing Brushire Records family (G. Love, ALO, Money Mark and Matt Costa ). Filmed over two nights at one of the band’s favorite venues, the film captures the magical connection between artist and audience, as well as providing glimpses at the creative process that yielded those crowd favorites. The total running time of the two disks exceeds 3 hours, and both feature stereo and 5.1 audio .