The denouement of the 1999 comedy Free Enterprise features William Shatner, playing a darker, misguided version of himself, rapping a rendition of Shakespeare’s Julius Caesar. The film, which received decent reviews, is about two friends, Robert and Mark, who are both approaching 30 and looking for love. The pals, huge Star Trek and Star Wars fans, are ecstatic when they meet Shatner (who insists they call him Bill), their idol. Well, Bill isn’t all that he’s cracked up to be — in fact, they meet him while he’s perusing a smutty magazine — a fact that inspires the men to drop the hero obsession and pursue their life’s desires. The New York Times called the film a “slight, bright, clever romantic comedy.” That’s all well and good, but just watch Shatner the rapper.
Next An Interracial Kiss