Matt Dillon wears a Rolex

Pat Healy is the private investigator Ted Stroehmann (Ben Stiller) hires to find Mary Jensen (Cameron Diaz), the girl Ted has not gotten over since high school. Matt Dillon plays Healy, who tracks Mary down to Miami, becomes fixated on her himself, and quits working for Ted to chase her. He feeds Ted lies to put him off, then spies on Mary and uses what he overhears to make himself into whatever she seems to want. Dillon plays the sleaze straight, which is most of why it works.

In the film's surveillance scene, Healy slumps in a car behind a parabolic microphone, and on his wrist is a gold watch on a gold bracelet with a pale dial. It has been catalogued as a Rolex Datejust, but no source documents the watch and the crown is not legible in the frame. What the camera shows is a gold dress watch in the Rolex idiom, a fluted-style bezel and a multi-link bracelet, which from this angle could be a Datejust or a Day-Date and cannot be confirmed as a genuine Rolex at all. Rolex introduced the Datejust in 1945 as the first self-winding wristwatch with the date shown in a window on the dial. Here it is gold, on a gold bracelet, with nothing in the frame to pin the brand or the model down.