David Letterman blunders through Kentucky Derby winner

A resurfaced phase from a 2014 episode of David Letterman reveals the tv persona playing a Kentucky Derby guessing game with comic Billy Eichner.

The 79-year-old icon was recognized to have Kentucky Derby–themed segments on his CBS program, The Late Show, which resulted in 2015, marking Letterman’s retirement after 33 years on the air.

The 152nd Kentucky Derby kicks off on May 2, 2026, at Churchill Downs in Louisville, Kentucky, with Derby Week starting on Saturday, April 25. The annual Triple Crown horse racing event attracts over 150,000 people every yr to observe as a 20-horse subject of 3-year-old thoroughbreds race 1.75 miles for a whopping $5 million pot. The clip resurfaced after Letterman admitted he’s ‘so glad to be out’ of late night time tv.

During the phase, called ‘Celebrity youngster or Kentucky Derby winner,’ Billy explained, “I am going to give you a name, these are all real names, you have to tell me if it’s a celebrity’s child or the name of a real Kentucky Derby winner.”

He repeated, “So, what they named their child or what someone named a horse in the Kentucky Derby.” With right solutions value $1 a pop, David stepped as much as the challenge.

With just 30 seconds on the clock, Billy fired off names like Pilot Inspektor, War Admiral, Blue Angel, Wintergreen, and Dust Commander.

Pilot Inspektor, he guessed incorrectly, is the youngster of actor Jason Lee, while Blue Angel is the daughter of U2 guitarist The Edge. After the game wrapped, Letterman insisted, “I want to keep going.”

They continued the phase, throwing out more distinctive names, like Diva Muffin, the daughter of musician Frank Zappa; Moxie CrimeFighter, the youngster of magician Penn Jillette, one-half of the duo Penn & Teller; and Jermajesty, the son of Jermaine Jackson.

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Billy continued with Equine monikers like Thunder Gulch, Flying Ebony, and Pink Star. Bluebell Madonna, not a horse, is the title of Spice Girl Geri Halliwell’s daughter, while Darby Rudd is the daughter of actor Paul Rudd.

He also listed the satirical title “Little Pixie Frou Frou,” which is often used to confer with the phenomenon of weird movie star child names.

The comic was a visitor on the present to advertise his program, Billy on the Street, which featured viral interviews with strangers like “For a Dollar,” “Name a Woman,” and “Dead or Boring.” David gushed, “I wish this was my show!” as Billy quipped, “You had your shot! Give someone else a turn!”

People attending “The Most Exciting Two Minutes in Sports” this yr can count on to listen to comparable names while ingesting refreshing Mint Julep cocktails in a sea of elaborate headgear. The 150-year custom consists of donning daring, wide-brimmed hats adorned with fascinators that includes feathers, flowers, ribbons, and other particulars.

The Kentucky Derby is predicted to see a large movie star turnout, particularly during the Barnstable Brown Gala on May 1, which is able to feature appearances by Patti LaBelle, Chaka Khan, Luis Fonsi, and *NSYNC’s Lance Bass and Joey Fatone.