Year: 1999
How Much Money He's Making: $7 million
What Will's Doing: Set in the Reconstruction era, Smith plays the flatly stoic companion to Kevin Kline’s doofiness as the two of them seek to bring down a Confederate war criminal and a mad steampunk scientist and an 80-foot hydraulic Tarantula. Smith sings a song about his character for the closing credits. The ditty won a Razzie, but also led to the most absurd live performance of all time wherein a maroon-suited Smith rides in on a stallion, receives a mid-song assist from Kool Moe D and Dru Hill, then raises Stevie Wonder through the floor who brings it home with a sparkling piano riff. Even the man’s failures are spectacular.