Whakaotihia te rerenga e whai ake nei: I te mutunga o te tau 1905, ka wehe atu a Harry i te tokotoru i muri i tana tautohetohe ki a Jolson. I whakakahoretia e Harry tana tono kia tiaki ia i a Joe Palmer, e noho ana i roto i te tūru wira. Whai muri i te wehenga o Harry, i mahi a Jolson raua ko Palmer hei tokorua engari kaore i tino angitu. I te tau 1906 i whakaae raua ki te wehe, a ko Jolson anake. I noho tonu ia ki te Globe me te Wigwam Theatre i San Francisco, a, i angitu ia i te motu katoa hei kaiwaiata vaudeville. Ka noho ia ki San Francisco, ka mea te
I hiahiatia e te hunga i whakangaromia e te ru te tangata hei whakakaha i a rātau. I te tau 1908, i hiahia moni a Jolson mo ia me tana wahine hou, a Henrietta, ka hoki ki New York. I te tau 1909, i aro mai tana waiata ki a Lew Dockstader, te kaiwhakanao me te whetu o nga Minstrels a Dockstader. I whakaae a Jolson ki te tono a Dockstader ka noho hei kaiwhakaari kanohi pango.