I was probably cool around the end of 2002.

Freeman’s line reads as dry, self-deprecating humor: he treats “cool” not as a stable identity but as a fleeting social verdict, pinpointed to a narrow window (“around the end of 2002”). The specificity suggests a wink at how arbitrary celebrity and cultural fashion can be—one moment you’re in, the next you’re not. It also implies an actor’s awareness of career timing: “coolness” may coincide with a breakout role, a sudden surge of attention, or a particular cultural mood, rather than any deep personal transformation. The understatement (“probably,” “around”) reinforces the joke that even he isn’t fully convinced by the label.