For the most part though, it was a failure. Not a commercial failure, mind you, Black Sheep‘s lifetime gross was only about $200,000 less than Tommy Boy. But posterity doesn’t care about that stuff. Black Sheep was so transparently an attempt to recapture the magic of Tommy Boy that watching it is bittersweet. It makes me nostalgic for David Spade and Chris Farley as a team, but feels so tone-deaf about what made Tommy Boy great (or at least intensely likable) in the first place, that you wonder if Tommy Boy was a fluke.
I don’t want to believe that, so instead I thought we might try to understand what went wrong. Black Sheep had Chris Farley and David Spade at the peak of their careers, plus Gary Busey and Penelope Spheeris, the director of Wayne’s World. As David Spade says in his recent memoir, Almost Interesting, “it should’ve been a slam dunk.” Even looking at it 20 years later, I agree.