After ten years of singing in nightclubs, Darrow received an offer to appear in Street Trash in which he played a mobster.
Darrow was also in the Woody Allen films Bullets over Broadway, Mighty Aphrodite, Deconstructing Harry, Small Time Crooks and Sweet and Lowdown.
Later the same year, he appeared in Mickey Blue Eyes with Hugh Grant and secured another role as mobster Larry Barese in the HBO hit series The Sopranos (1999–2007).
Along with Gambino crime family soldier Joseph "Joey Boy" Orlando and associate Giovanni "Johnny" Monteleone, Darrow was accused of ordering the maiming of a man in Monticello, New York, who owed money to a loan shark.
[1] Darrow and Orlando both pleaded guilty in federal court to these charges in February 2011, in exchange for a sentence of up to 33 months.