At 59 years old, jockey Mike Smith is taking the nickname "Grandpa" in stride—and he's about to make history. This Saturday, May 2, at Churchill Downs, Smith will ride So Happy in the Kentucky Derby, aiming to become the oldest jockey ever to win the prestigious race.

"I get it all, man," Smith says with a laugh, referring to the age-related jokes from his peers. But he's quick to add, "At my age, I'm still doing the things I was doing when I was 30, man. It's crazy."

Currently, the record for the oldest jockey to win the Kentucky Derby belongs to the legendary Willie Shoemaker, who was 54 when he rode Ferdinand to victory in 1986. Smith, who was 52 when he won the race in 2018 aboard Justify, is no stranger to the winner's circle—and he's no long shot to break Shoemaker's record this time around.

Smith will be riding So Happy, a 7-1 contender trained by Mark Glatt. Despite having access to younger, more agile jockeys, Glatt never considered anyone else for the mount. "He keeps himself in prime condition," Glatt explains. "And especially in a race like the Derby, how do you replace the experience that a rider like Mike Smith has?"

This year marks Smith's record 29th appearance in the "Run for the Roses." His history at Churchill Downs includes two unforgettable victories: in 2005, he guided 50-1 longshot Giacomo to a stunning upset, and in 2018, he rode Justify to a Triple Crown triumph. Now, he's eyeing a third win that would cement his legacy as the oldest jockey to conquer the Derby.

"You're always excited to make it to the Derby, especially when you make it with one that's really a true contender," Smith says. "And I think this horse showed in the Santa Anita Derby that not only is he going, but he actually has a big chance to win it all. He really does."

So Happy's journey to the Derby has been remarkable. The horse debuted at 38-1 odds and won, then placed third in his next outing before winning two more races—including the Santa Anita Derby, which secured his spot in the field. "I think we're just starting to see the best of him," Smith adds.

Whether you're cheering for history or just love a good underdog story, Smith and So Happy are a duo worth watching this Derby weekend. And if you're inspired by the spirit of the race, now's the perfect time to gear up in your finest Derby attire—because even if you're not in the saddle, you can still look like a champion.