Glitter is considered one of the worst movies ever made, and Mariah Carey's dismal performance contributed a lot to that awfulness. The Razzie thoroughly enjoyed the train wreck; they awarded Carey the Golden Raspberry Award for Worst Actress and nominated her cleavage for Worst Screen Couple.
Madonna has long been the poster child for bad singers-turned-actors, especially with her Razzie-winning role in Shanghai Surprise. However, she did surprise everyone with an impressive performance in Evita. But any goodwill she earned for her role as Eva Perón was lost after starring in 2002's 'Swept Away'. Her performance was so bad that the Razzies nominated her as Worst Actress of the Decade in 2010.
It was supposed to be his version of Eminem’s 8-Mile, but it was a lot closer to a thugged-out version of Mariah Carey’s Glitter. Get Rich or Die Trying just showcased 50 Cent's limited acting range, even when working on such clichéd materials.
It's fortunate that Kelly Clarkson has had a successful music career since her acting career was DOA after the release of From Justin to Kelly. She hasn't appeared in a feature film ever since starring in this gem that currently sits on the 13th spot of IMDB's Bottom 100 movies of all time. A special nod goes out to Justin Guarini, who was just as equally bad as Clarkson.
20th Century Fox
Yes, this actually happened. Vanilla Ice starred in an actual movie that's probably more awful than you can imagine. Watching him vocalize his tough-guy lines with such stilted acting will probably hurt more than brain freeze.
Even if you're a Britney fan, it's hard not to shudder watching the singer try to act. Many thought Crossroads was a better effort than Mariah Carey's Glitter, but that's not saying much. Britney's thespian efforts netted her the ignominious distinction of winning the Golden Raspberry for Worst Actress.
Not that Once Upon a Time in Mexico would've been much better without him, but Enrique's Iglesias' presence stood out for all the wrong reasons. His uninspired performance couldn't compare to Antonio Banderas and Johnny Depp, who looked like they were having fun in Robert Rodriguez's over-the-top western.
How to make a bloated summer blockbuster about a children's board game even worse? You simply cast Rihanna as a tough-as-nails gunner. Thankfully, Rihanna only had a small part because who knows just how much quicker Battleship would have sunk with her in a bigger part.