Pedzisa mutsara unotevera: Pakupera kwa1905, Harry akasiya boka racho pashure pokunge apopotedzana naJolson. Harry akanga aramba chikumbiro chake chokutarisira Joe Palmer, uyo akanga ari muwiricheya. Pashure pokuenda kwaHarry, Jolson naPalmer vakashanda vari vaviri asi havana kubudirira zvikuru. Pakazosvika 1906 vakabvumirana kuparadzana, uye Jolson akanga ari oga. Akava wenguva dzose paGlobe uye Wigwam Theater muSan Francisco uye akabudirira munyika yose semuimbi wevaudeville. Akatanga kugara muSan Francisco, achiti
Vanhu vakanga vaparadzwa nokudengenyeka kwenyika vaida mumwe munhu wokuvanyaradza. Muna 1908, Jolson, achida mari nokuda kwake amene nomudzimai wake mutsva, Henrietta, akadzokera kuNew York. Muna 1909, kuimba kwake kwakacherechedzwa naLew Dockstader, mugadziri uye nyeredzi yeDockstader's Minstrels. Jolson akabvuma kupiwa kwaDockstader ndokuva mutambi ane kumeso kwakasviba.