William Shakespeare's classic tragedy Romeo & Juliet is loosely adapted and modernized in director Rowland V. Lee's Guilty Generation. Set in 1930's New York, rival gangster families the Palmero's and the Ricca's play Lee's version of the infamous Montagues and Capulets. The two mobs had once co-existed peacefully, but split after a terrible argument, causing a long-standing and deadly rivalry. Maria Palmero (Constance Cummings), the daughter of gangster Mike Palmero (Leo Carillo), meets and falls in love with a young architect played by (Robert Young). Though Young's character goes by the name of John Smith, his true identity is none other than Marco Ricca--the son of Mike's (Carillo) rival. Due to the war waged by their families, Maria and Marco try to keep their affair and ultimate marriage to one another secret. Unfortunately, Maria's father realizes the two have married and vows to kill Marco, who had earlier killed Maria's brother. Tragically, the Palmero family patriarch is only stopped with a bullet from his own mother's (Emma Dunn) gun.