Kammala jumla mai zuwa: Jackson ta jawo hankalin William Morris Agency, wani kamfani wanda ya inganta ta ta hanyar yin rajista a manyan dakunan kide kide da wake-wake da kuma fitowar talabijin tare da Arthur Godfrey, Dinah Shore, Bing Crosby, da Perry Como a cikin shekarun 1950. Girmamawarta da farin ciki, halin kirki ya sa ta zama abin so ga masu samar da ci gaba da masu shirya shirye-shirye da ke ɗokin nuna baƙar fata a talabijin. Ta bayyana a
Babban Taron Jam'iyyar Democrat na 1956, yana yin shiru a cikin zauren masu halarta tare da "Na ga Allah". Miller, wanda ya halarci taron, ya yi mamakin wannan, ya ce "ba wanda ya yi barci sa'ad da ta shiga gidan". Jackson ya shiga fina-finai yana wasa da mishan a cikin "St. Louis Blues" (1958), kuma mawaƙin jana'iza a cikin " kwaikwayon rayuwa " (1959). Game da buƙatar ta, ta yi tafiya mai yawa, tana yin wasan kwaikwayo 200 a kowace shekara har tsawon shekaru goma. Ita da ƙungiyar mawaƙa da masu rakiyarta sun yi yawon shakatawa zuwa cikin Kudu, suna fuskantar wahalar samun wurare masu aminci, tsafta don barci, ci, da siyan gas saboda dokokin Jim Crow. A wasu lokatai sukan kwana a cikin motar Jackson, motar Cadillac da ta saya domin tafiye-tafiye masu nisa su kasance da sauƙi. Jackson ya tuna, "Ganin fushin da muke gani a cikin mu masu launin fata da ke zaune a cikin mota mai kyau sun kasance masu ban tsoro don ganin... Mun zama kamar muna rayuwa ne a kan jakunkunan 'ya'yan itace da rana kuma muna tuƙi rabin dare, kuma na gaji sosai a lokacin da ya kamata in yi waƙa, har na kusan yin jiri". Jackson ya fara samun nauyi. Ta kuma koyi halaye na musamman game da kuɗi. A matsayinta na bakar fata, Jackson ta ga sau da yawa ba zai yiwu a biya kudade ba lokacin da yake nesa da Chicago. Saboda haka, kwangilarta ta bukaci a biya ta da kuɗi, sau da yawa tana tilasta mata ta ɗauki dubban daloli a cikin jakunkuna da kuma cikin tufafinta.