By 1991, even the most retrograde of old fogies was starting to suspect that rap music was not going away anytime soon. Advertisers began mining it for every bit of cultural capital they could, and soon hip-hop would be used to sell everything from breakfast cereal to high fashion. It became shorthand for “relevant,” and a nifty cultural touchstone that was sure to resonate with the youth… right? “Cutting-edge” and “hopelessly dated” are not mutually exclusive categories—a lot of groundbreaking things simply look silly in retrospect. Dan Aykroyd’s Nothing but Trouble however, was just completely, unjustifiably bad from the beginning.

The Razzie-winning box office bomb actually had a lot going for it in terms of star-power. In addition to John Candy and Demi Moore, Aykroyd was just coming off the Ghostbusters sequel, and Chevy Chase had finished his final National Lampoon’s Vacation movie. Unfortunately Aykroyd’s success may have have burdened him with a bit of artistically unproductive hubris. He directed the film, co-wrote the screenplay with his brother and co-starred in the movie (almost never a good sign). For a little perspective, this was a movie with the $40 million budget—massive for that time—and the box office take didn’t even reach $8.5 million.
 

 
Aykroyd also decided that Oakland hip-hop group Digital Underground (you know, the guys who did “The Humpty Dance”) could spice up the movie with a musical number—with Dan Aykroyd and Chevy Chase’s ultra-white guy characters as the enthusiastic audience. Most notably, this means a cameo by a young Tupac Shakur in the most undignified role of his short life. I’d be absolutely shocked if anyone predicted a future in music for Shakur based on this performance—it’s literally one of the worst moments in hip-hop history.