4. Adam Sandler - Jack and Jill (2011)
The continued success of the cinematic exploits of Adam Sandler are one of the mysteries of cinema that I just can't seem to get my head around. Somehow, he has remained one of the most consistently well-paid and bankable stars in Hollywood for almost 20 years, despite the vast majority of his movies being awful. Since 1998, Sandler has had no less than 14 movies cross $100 million at the domestic box office, which is an incredible track record for any actor. However, Jack and Jill was not one of these movies. It merits its place on this list due to the sheer awfulness of the final product. Jack and Jill grossed almost $150 million worldwide despite a well-earned reputation of one of the worst films ever made. As well as continuing the career degradation of Al Pacino, the movie received 12 nominations across 10 categories at the Razzie Awards, winning in every single one. It's nothing short of ridiculous that someone could earn so much from such a bad movie. Despite featuring prominently in almost every 'worst of' list for the year, Sandler's role as star, co-writer and producer (via his Happy Madison Productions) banner saw him walk away with the movie with over $20 million. I subjected myself to Jack and Jill to see if it merited inclusion in the article, and I sincerely regret it. My eyes cannot unsee the horrors I witnessed.