1. The 1930s saw several firsts at the Kentucky Derby. Lawrin's victory in 1938 was the first won by trainer Ben Jones and jockey Eddie Arcaro, who would team up to win a record four Derbies together. There was also the first (and so far only) father-son duo to win the Triple Crown, Gallant Fox (1930) and Omaha (1935). The year 1933, though, produced what is most likely a last in Kentucky Derby history when Brokers Tip edged Head Play in the famous "Fighting Finish." The Derby proved a maiden-breaking win for Brokers Tip, who never won another race.
2. A staple on network radio and movie newsreels for years, the pageantry and excitement of the Kentucky Derby first became available to a live nationwide viewing audience in the 1950s. In 1952, CBS televised Hill Gail's victory, the sixth winner in the Derby for Calumet Farm and a then-unprecedented fifth for jockey Eddie Arcaro. The following year Native Dancer became Thoroughbred racing's first star of the television era. Easy to spot on the black & white sets of the era, the "Grey Ghost" unfortunately suffered his only career defeat in 22 starts when a troubled second in the Derby to longshot contender Dark Star.
3. The 1960s produced its share of legendary Kentucky Derby winners, but also a record number of horses that won the first two legs of the Triple Crown but failed to pull off the three-race sweep in the Belmont Stakes. Carry Back (1961), Northern Dancer (1964), Kauai King (1966), Forward Pass (1968), and Majestic Prince (1969) all kicked off their quests with victories over the Churchill Downs strip (Forward Pass' was via disqualification). Repeating in the Preakness two weeks later, they all fell short in the 1 1/2-mile Belmont by generally significant margins.
4. Soon after beginning its second century of existence, the Kentucky Derby became a tough nut to crack for the betting favorite. Starting at the dawn of the 1980s, the post-time favorite suffered 20 consecutive losses in the Run for the Roses. Numerous second choices won, though, including the filly Winning Colors in 1988, who was narrowly eclipsed in the Win pool by Private Terms. Fusaichi Pegasus ended the favorites' losing skid in 2000, and in the ensuing 17 years eight favorites have won, including an unprecedented five straight (2013-17).
5. While favorites won four times in the 2000s, the decade will also be remembered for yielding the two biggest upsets in living Kentucky Derby memory. Both Giacomo (2005) and Mine That Bird (2009) were sent away at odds of 50-1, with Giacomo returning $102.60 and Mine That Bird $103.20. However, both payoffs were well short of the record payoff of $184.90 set by Donerail way back in 1913. The highest odds any horse has started at in the Derby since 2009 was 69-1.