Every year in the annual Oscar race there are always a few surprises, head scratchers or genuinely odd contenders that make you wonder how they were ever selected. Was it politics? Was it a fluke? Did good taste or bad taste actually triumph? Here is a list of my favorite oddities, some of which deserved their nomination though I never expected the Academy to acknowledge them because they were either low-budget indies, big budget genre pictures or under the radar movies that were barely noticed by moviegoers. I’m using the 1990s as my starting point and working backwards from there, cherry picking specific Oscar races, since most of the more interesting anomalies occurred prior to the 21^st century.

Yes, there have been a few unexpected contenders since then such as 2000’s strange and mesmerizing Shadow of the Vampire (nominated for Best Supporting Actor – Willem Dafoe) and Hustle & Flow featuring the Oscar winning Best Original Song of 2005 – “It’s Hard Out Here For a Pimp.” In fact, the Best Original Song Oscar category is usually the place to look for oddball entries such as “Blame Canada” from South Park: Bigger, Longer & Uncut (1999) by the demented director-writer team of Trey Parker and Matt Stone or “How Do I Live,” written by Diane Warren and performed by Trisha Yearwood in Con Air (1997), an outrageous over-the-top action thriller from producer Jerry Bruckheimer. But, in general, the Academy Award nominations from 1999 on back to the beginning were quirkier and more fun.