5th Season Premiere: "Hello Charlie" - 10/18/00
In the fifth-season opener debuting Charlie Sheen, yet another bona fide star is replaced by a questionable commodity. But rather than whitewash Sheen's tarnished image -- lately he's better known for his connection to Hollywood madam Heidi Fleiss than for his film roles -- the show exploits it. The actor plays Charlie Crawford, Mike's tabloid-fodder successor as deputy mayor of New York, and his rep is used to fuel some improbable plot twists. First, a hotel tryst with a flight attendant makes Charlie late for his first press conference. Then, a crucial deal is compromised because a scornful lady lawyer (Marcia Cross) is still peeved over getting jilted by Charlie, who doesn't recall their romance because he was wasted at the time.