The higher the stakes, the more the late Dale Earnhardt relished the challenge.

And nowhere did Earnhardt’s star shine brighter than in the Sprint All-Star Race — then known as “The Winston” — at Charlotte Motor Speedway.

Earnhardt was one of only three drivers — Jimmie Johnson and Jeff Gordon were the other two — to win the annual May classic three times.

Earnhardt captured his first Sprint All-Star Race victory in 1987, the year of the infamous “pass in the grass” that wasn’t a pass at all. He followed it up with additional all-star victories in 1990 and ’93.

In the accompanying video NASCAR Race Hub looks at Earnhardt’s greatest all-star moments and his most controversial. Enjoy!

Tom Jensen is the Editor in Chief of SPEED.com, Senior NASCAR Editor at RACER and a contributing Editor for TruckSeries.com. You can follow him online at twitter.com/tomjensen100.