Bad Apple (2004)

When a tough-talking FBI agent goes undercover to infiltrate a mob loan-sharking operation in the Big Apple, a fling with his informant's sister threatens to derail the entire investigation in this dark crime comedy from veteran film and television director Adam Bernstein. A streetwise agent who knows how to talk the talk and walk the walk, G-man Mike Tozzi (Chris Noth) is hot on the trail of high-ranking mobsters "Buddha" Stanzlone (Elliott Gould) and Tommy "Bells" Bellavita (Robert Patrick). Though Tozzi and his partner, Cuthbert Gibbons (Colm Meaney), are well on their way to finding the evidence they need to break the case, a severe lapse in judgment finds the womanizing Tozzi entering into an ill-advised fling with his informant's alluring sister, Gina (Dagmara Dominczyk). As the disastrous romance draws the FBI agents and the mobsters into a deadly game of cat and mouse, the only thing that's certain is that viewers will have a pulse-pounding good time finding out who will come out on top.