The 1927 film The Jazz Singer stands as a unique cul­tur­al arti­fact of its time. Usu­al­ly hailed as the first talk­ing pic­ture, it was also one of the hand­ful of motion pic­tures (and per­haps the most seri­ous) that rep­re­sent­ed Jews on screen — in a peri­od when Jews were known as hav­ing invent­ed Hol­ly­wood but oth­er­wise kept their Jew­ish iden­ti­ty under the radar. The film stars Al Jol­son, once acclaimed (often by him­self) as the ​“world’s great­est enter­tain­er.” The plot is inspired by Jolson’s life story.

Jour­nal­ist Richard Bern­stein regards Jolson’s rise to fame and the mak­ing of the film as an arche­typ­al Amer­i­can sto­ry: a unique tal­ent flour­ish­es in an atmos­phere of free­dom — hence the book’s title. Along the way, Bern­stein exam­ines many dimen­sions of Jew­ish life in Amer­i­ca, such as the his­to­ry of the Jews in the enter­tain­ment indus­try both as sub­jects and as cre­ators, and the nature of Jolson’s pro­fes­sion­al per­sona as a black­face per­former. Some of this is well-trod­den ter­ri­to­ry, but Bern­stein has pro­duced an engag­ing and com­pact cul­tur­al his­to­ry, rich with research and insight.

Jol­son was the sec­ond son of an immi­grant Ortho­dox rabbi/​cantor named Moshe Yoel­son (Al was orig­i­nal­ly named Asa; his old­er broth­er, Har­ry, was Hirsch). While Rab­bi Yoel­son con­tin­ued his old-world Ortho­dox life and hoped his sons would fol­low in his foot­steps, his two sons broke away to become street per­form­ers and even­tu­al­ly vaude­ville come­di­ans. Like many oth­er young Jews of that gen­er­a­tion and the next (among them, the Marx Broth­ers, Sophie Tuck­er, Fan­ny Brice, and Eddie Can­tor), Al thrived in vaude­ville and found his way to fame; with­in fif­teen years of leav­ing his par­ents’ tra­di­tion, he was head­lin­ing in Broad­way revues writ­ten by anoth­er fam­i­ly of Jews, the the­atri­cal impre­sar­ios the Shu­berts, and belt­ing out tunes redo­lent of the Old South. Bern­stein wades through many of the con­tra­dic­to­ry points of view on Jolson’s per­for­mance in black­face and argues that the use of black­face by Jews was not nec­es­sar­i­ly racist in intent. His argu­ment is not entire­ly con­vinc­ing, but nei­ther are many of the alter­na­tive inter­pre­ta­tions he cites. Nonethe­less, the book pro­vides an in-depth con­text for under­stand­ing this fraught part of the Amer­i­can story.

Jol­son was among the high­est-earn­ing per­form­ers in the busi­ness, and his career flour­ished over sev­er­al decades. His life sto­ry inspired a young Jew­ish writer, Sam­son Raphael­son, to write a short sto­ry enti­tled ​“Day of Atone­ment,” which was pub­lished in 1922 and lat­er adapt­ed for the stage and screen. Bern­stein ana­lyzes the var­i­ous ver­sions (and sub­se­quent remakes) and shows how the changes in the nar­ra­tive reflect the chang­ing sta­tus of Jews in Amer­i­ca. Raphaelson’s sto­ry empha­sizes the ways in which Jew­ish tra­di­tion and Jazz music con­verge when a cantor’s son wants to make it big in pop­u­lar enter­tain­ment — to the con­ster­na­tion of his tra­di­tion­al father. The film adap­ta­tion high­lights the clash of tra­di­tion and moder­ni­ty and seems to come down on the side of tra­di­tion when Jack, the Jol­son char­ac­ter, replaces his father in singing Kol Nidre on the very night he was to make his Broad­way break­through. How­ev­er, Hol­ly­wood being Hol­ly­wood, Jack also goes on to tri­umph on stage. Lat­er ver­sions min­i­mize the clash of tra­di­tions and empha­size the theme of ​“mak­ing it” in America.

One of the most inter­est­ing themes Bern­stein explores is the risk the Warn­er Bros. stu­dio (found­ed and run by immi­grant Jews) ran in explor­ing the clash of Jew­ish tra­di­tion and moder­ni­ty in their pio­neer­ing film. Ulti­mate­ly, how­ev­er, the film was both a pop­u­lar suc­cess and a tri­umph of new tech­nol­o­gy, appeal­ing to audi­ences across demographics.