Kentucky Derby's legendary races never get old: seven to watch again and again

Every Kentucky Derby is memorable in its own way, whether for controversy, a close finish or the enduring legacy of the winner.

But some have aged better than others as visual and visceral reminders of how beautiful, exciting and organic horse racing can be as a tableau for what's great about sports.

As the Derby reaches its 150th running, here are the "Scintillating Seven" editions you'll want to watch again and again.

Unbridled, 1990 

One of the most beautiful moments in the race’s history took place as Unbridled roared past Summer Squall with a powerful stretch run. But as impressive as his performance was, the lasting legacy of that day came thanks to ABC putting a camera on trainer Carl Nafzger and Frances Genter, the 92-year-old owner who had been involved in horse racing for 50 years but never won the Derby. 

Because of Genter’s failing eyesight, she had trouble seeing her horse during the race. So Nafzger narrated what was happening, and it became legendary television.

“He's taken the lead! He’s taken the lead! He’s on the lead Mrs. Genter, he’s on the lead! He’s gonna win! He’s gonna win! He’s gonna win! He’s a winner! He’s a winner, Mrs. Genter! There he goes, right there! He's a winner, he’s a winner, He’s a winner! He’s a winner! We won it! We won it! You won the Kentucky Derby! Oh Mrs. Genter, I love you.”

Nafzger’s race call and Genter’s reactions were so pure and unscripted, you couldn’t recreate it if you tried. And even all these years later, it’ll bring a tear to your eye every time. 

Alysheba, 1987 

As the field hit the top of the stretch, it became clear this was going to be a two-horse race between Bet Twice, who had made the lead, and Alysheba, who had come from back in the pack and circled the field around the far turn. But as they came off the turn, Bet Twice veered from his path and right into Alysheba’s running lane. That convergence caused the horses to clip heels — a dangerous scenario that could have resulted in one of them falling down and creating a potentially tragic scene. Instead, Alysheba stumbled briefly but stayed on his feet, went immediately back to racing and caught Bet Twice inside the eighth pole to win by three-quarters of a length. 

“I thought I was gone,” jockey Chris McCarron said in Sports Illustrated’s recap of the race. “It was unbelievable. But he regained his balance, and when he did, he put me back in the saddle. At that point I didn’t think I was gonna win it. I'm riding for my life, hoping to be second, because I thought they’d take Bet Twice’s number down if he won. I had no idea my colt could recover from that and win.” 

Grindstone, 1996

There’s almost never a true photo finish at the Derby. But when Grindstone and Cavonnier hit the wire together, the result was so much in doubt that even announcer Dave Johnson on ABC had to stop for a beat and characterize it as “Too tight to call!” In an interesting twist, the cameras immediately panned to a smiling Bob Baffert, who trained Cavonnier, and then a concerned-looking D. Wayne Lukas talking to Grindstone owner William T. Young. 

“We jumped up and started hugging and congratulating one another,” Lukas said, according to the New York Times. “Then it struck me and I thought, 'Maybe we didn't even win.' "

Nobody in the stands could tell. Even the jockeys – Jerry Bailey on Grindstone and Chris McCarron on Cavonnier – didn’t know. Tension was in the air for several minutes as the stewards looked at the photo. Eventually, Grindstone was declared the winner of the closest finish in Derby history: Exactly a nose on the wire. 

It was Lukas’ third Derby win of four in his legendary career. And it was a brutal disappointment for Baffert, a 43-year-old relative newcomer to the top level of racing who was in the Derby for the very first time. Of course, Baffert would return the very next year to win with Silver Charm and then again in 1998, 2002, 2015, 2018 and 2020 to become the most dominant force in the sport. 

Whirlaway, 1941

There aren’t a lot of quality videos from this era of horse racing, but there’s no mistaking Whirlaway, the horse they called “Mr. Longtail” because of the unusually long, thick tail that seemed to flap around like a flag in the breeze as he left his competition in the dust. 

In the Derby, it looked like anyone’s race at the top of the stretch. But in just a few jumps, Whirlaway emerges and accelerates so dramatically that the only thing you notice is his tail leaving everyone else behind. By the end of the race, Whirlaway had won by eight lengths, which remains tied for the largest winning margin in the history of the race. 

Whirlaway went on to win the Triple Crown as part of a remarkable career that saw him race 60 times with 32 wins and Horse of the Year titles as both a 3- and 4-year old. 

Canonero II, 1971 

One can only imagine what fans and other horsemen were thinking as the unknown jockey in brown silks and a mystery horse from Venezuela came from 18th place down the backstretch, blew by everyone on the far outside and won America's most prestigious race by nearly four lengths. 

Though the payout didn’t reflect it, because Churchill Downs at that time grouped the six longest-shots in the race into a “mutual field” and Canonero II couldn't be bet on individually. This was arguably the biggest upset in Derby history. And it would have been impossible to see coming. 

Bred in Kentucky, Canonero II was sold as a yearling for $1,200 and taken to Venezuela. He went to California for a pair of races as a 2-year-old but made no impact in either, was shipped back to Caracas and won five of his nine races there against presumably poor competition. His trip to the Derby was interrupted by two mechanical issues on the flight over, a four-day quarantine in Florida and a van ride to Kentucky that left him looking sickly. At Churchill, he breezed half a mile in an extremely slow 53 4/5 seconds and was pretty much laughed off the track – until he sprinted off the final turn. 

Canonero II came back two weeks later and won the Preakness as well, securing his place as a horse-racing folk hero. 

Genuine Risk, 1980

Could a filly beat the boys? That was the big question heading into the Derby because it hadn’t been done since Regret in 1915. In fact, it had been more than 20 years since a filly even tried. 

The interesting part of the story came after the Wood Memorial Stakes, a traditional Derby prep in which Genuine Risk finished a disappointing third. After the race, trainer LeRoy Jolley declared there was no way she would contest the Derby. He was an old-school trainer, squeamish about pitting a filly against the colts. He thought it was too big a risk for her health and future prospects – a genuine risk, as it were. 

But owners Bert and Diana Firestone wanted to run in the Derby and didn't think the 3-year-old crop that year was very strong. After some defections that left the race with only 13 starters, Jolley got on board and Genuine Risk was in the starting gate as a 13-1 long shot. 

From an outside stalking position down the backstretch, Genuine Risk tracked down favorite Rockhill Native at the quarter pole and cleared the field entering the stretch. From there, it was just a matter of whether she had enough stamina to hold off charges from Jaklin Klugman and fast-closing Rumbo. With a terrific ride from Jacinto Vasquez, she crossed the wire about a length in front and made the cover of Sports Illustrated under the heading, “The Lady Is a Champ.” 

Barbaro, 2006

When you watch this race, what sticks out the most is how hard the other horses are running and how easy Barbaro is making it look as he pulls away from them. That perhaps explains why this horse was so beloved during his life and still remembered nearly two decades after his death. 

It was, of course, one of the worst days in the history of the sport when Barbaro’s right hind leg shattered just a few jumps out of the gate in the Preakness, beginning months of surgeries and rehab and health setbacks that ultimately ended with his death the following January.

But on Derby Day, Barbaro was a majestic sight to behold as he left his competition far behind and won by an easy 6 1/2 lengths under almost no urging from jockey Edgar Prado. 

At that point, Barbaro was six-for-six in his career and on track to possibly become one of the best Thoroughbreds in the history of the sport. After winning the Derby in a fast time of 2:01.36 with seemingly lots in reserve, the Triple Crown seemed like a real possibility. 

Though the story ended in shock and tragedy just two weeks later, his Derby run remains one of the most visually impressive performances in the history of the race.