The Daytona 500 is the most prestigious race in NASCAR, which means those who win it experience the highest high the sport can provide. But those who fall just short experience a heartbreak like no other. Here are the five most heartbreaking Daytona 500 losses in the race's 67-year history.

Greg Biffle made his NASCAR Cup Series debut in 2002 and spent 14 years as a full-time Cup Series driver. He was 55.