Kammala wannan jumla: Will ya shiga wasan kwaikwayo na Wild West kuma yawon shakatawa a duniya, sa'an nan ya sadu da Betty a
1904 St. Louis World's Fair kuma ya gabatar da ita. Bayan sun yi aure, sun haɗu da hutun amarcinsu tare da ɗayan yawon shakatawa na Will, wanda ya ƙare a Madison Square Garden na New York. A can ya zama gwarzo ta hanyar lasso wani bijimi mai haɗari wanda ya saki yayin wasan kwaikwayo. Labarin jaridar ya jawo hankalin Bert Lynn, wanda ke gudanar da kamfanin talanti. Ya shawo kan Rogers mai son yin wasan kwaikwayo a cikin vaudeville, amma aikinsa na rodeo ba ya sha'awar masu sauraro. Bayan watanni shida na rashin aikin yi kuma tare da jaririn da za a haifa ba da daɗewa ba, Will ya hau kan mataki a matsayin maye gurbin minti na ƙarshe kuma an tilasta masa yin aikinsa shi kaɗai, ba tare da dokinsa ba. Bayan wasu dabaru na igiya sun kasa, sai ya yi magana da masu sauraro; maganganun wasan kwaikwayonsa na gida yana da babbar nasara. Wannan ya ba shi wuri a cikin Ziegfeld Follies; ya zama ɗaya daga cikin abubuwan jan hankali. Ya kara da sharhin siyasa ga aikinsa kuma ya zama sananne a matsayin "masanin falsafa" wanda aka sani da maganganu masu ban sha'awa game da 'yan siyasa da kuma al'amuran yau da kullum.