These Celebs Reveal Why the Kentucky Derby Is the Hottest Event on Their Spring Calendars

Thu May 06 2021

The legendary event of the spring, also known as the Kentucky Derby, draws in an audience from near and far. Whether you love wearing big hats, you’re a horse fanatic, or just looking for a good time – the Churchill Downs is the place to be during the first weekend of May. And nothing can be labeled an iconic event unless there’s a crowd of famous people attending, so of course, celebrities from all industries can be found at these renowned races.

Your favorite athletes, singers, influencers, and entertainers are considered loyal patrons to the party and consider this THE event of the spring that they refuse to miss. Some come for the lavish looks they can only wear once a year, some are actually interested in the horse races, and some just come to live their best lives with their fellow famous friends. Either way, we know all the celebrities that adore the Kentucky Derby and the reasons they return.

Bobby Flay Is Hot for Horses Just as Much as He Is For Cooking

Everyone knows Chef Bobby Flay has a flair for food. But what most people don’t know is that he has a passion for horses that is just as strong as his love for cooking. In fact, he’s more than just a horse racing fan – he even owns his own horses and likes to participate in the betting aspect of the races as well. Needless to say, it’s obvious that the Kentucky Derby is a staple in Bobby’s social schedule year after year.

Even if Bobby doesn’t have any of his own horses competing in the derby, he will always show up and show his support for the love of the sport. He’s also obsessed with the fact that for only two dollars, he can express whatever opinions he wants on the track. Because as is, horse racing is the only sport where you can express your opinion on the outcome and back up your choice with money. We can only imagine how much he bets every year.

Megan Huckaby From Woodford Reserve Provides the Key Ingredient to the Perfect Mint Julep

When the signature drink of the Kentucky Derby is a mint julep, with the main ingredient being bourbon whiskey, you can bet the biggest names in the whiskey world are going to be in attendance. Easily, this makes Megan Huckaby, the marketing extraordinaire for Woodford Reserve, a yearly regular at the event. And dressed for the occasion, she even sported a customized mint julep hat to complete her look for the 2019 derby red carpet.

What’s known as celebrating the most exciting two minutes in sports history, is always accompanied with a drink in hand. And Megan Huckaby makes sure that her whiskey company is the one that’s mixed into the cocktails for all the derby drinkers. Not to mention, she loves a good reason to get dressed up. Cheers to that!

NeNe Leakes Loves to Show Her Face at Any Major, Elite Social Gathering

Whether or not you’ve watched The Real Housewives of Atlanta, we already know that you know exactly who NeNe Leakes is. That being said, if there’s a glamorous event happening, her name better be on the guestlist, or she’ll find a way to put herself on it. And the Kentucky Derby is no different from any other headlining affair in her eyes.

Though she may not have acquired many friends during her time on the TV show, that won’t stop her from being considered an A-lister no matter where she goes. And per usual, this Georgia Peach showed up and showed out in style at the 2019 Kentucky Derby, flaunting a sunshine yellow gown paired with a mystical butterfly headpiece to enchant any passerby she came across.

Carson Kressley Is Addicted to Placing Bets on the Horses

Just when we thought Carson Kressley was an open book, he has shocked the world by revealing one of his unusual vices. Not only does he have impeccable style and an infectious personality, but he’s actually quite good when it comes to placing bets on winning horses. From styling and providing makeovers to those in need on Queer Eye for the Straight Guy to successfully betting on horses, he is truly a rare gem. Is there anything this diva can’t do?

But word on the street is that his betting methods are a bit precarious. In the beginning, he admitted that his strategy was based on the fact if he did or didn’t like the color of the jockey’s uniform (as would we). When he realized that this wasn’t working, he started to base them on the horse’s appearance. Now, as a seasoned better, he studies past performances of the competitors and occasionally takes suggestions from seasoned wagerers as well.

Jennifer Nettles Received the Ultimate Honor by Singing the National Anthem at the Kentucky Derby

She’s a country queen hailing from the South – she’s none other than Jennifer Nettles, the lead singer of the country band Sugarland. While some artists consider it a milestone in their career to sing at the Super Bowl Halftime Show, this boot-scootin’ vocalist made it big when she was asked to sing the national anthem at the 2019 Kentucky Derby.

Performing in front of about 160,000 people in the audience, Jennifer kicked off the whole show with her rendition of the “Star-Spangled Banner” and made sure to have the perfect outfit for the occasion as well. Rocking a couture hat designed by the famous Arturo Rios, this alone was enough to entice Jennifer to the derby; singing was just an added bonus.

Joey Fatone Has Attended the Kentucky Derby for Over 18 Years Because He Loves to Party Like a Southern Gatsby

For the past 18 years, former NSYNC heartthrob Joey Fatone has yet to miss a Kentucky Derby. This weekend has been permanently blocked out on his calendar for the rest of his life. Ever since Joey was invited with the other boy band members at the peak of their career – the southern hospitality, glamour, and all-around good time has captivated Joey so much that this is the one event he continues to look forward to year after year.

Every year, Joey always arrives within a group of about five friends and makes sure to bring someone new. He kind of feels indebted to the derby for the best memories he’s made and wants everyone to love it as much as he does. From siblings to childhood friends to acquaintances, Joey has made sure to include just about anyone in his derby gang.

Nicole Kidman Has Been Riding Horses Her Whole Life

From the time she was three years old, Nicole Kidman has been riding and fawning over horses. But standing at a solid 5’11”, she’s just a bit too tall to be considered as a jockey. So instead, Nicole prefers to ride recreationally in her free time and attend the Kentucky Derby to see all the beautiful horses that compete.

Not to mention, she’s also married to country singer Keith Urban, so it’s a given that the pair will always be seen at the sporting event. We can only imagine how Nicole must silently critique all of the riders from the sidelines – can you say, intimidating? And she always looks stunning in her big hat and chic gown, so she’s pretty much perfect.

Alex Trebek Owned Horses That Competed in the Kentucky Derby

We all know Alex Trebek as the OG game show host from Jeopardy! But when he wasn’t on the big screen, he was occupied tending to his horses in the stables. Yup, Alex was a horse lover who even owned a farm in California. Back in the 90s, he even bought a breeding and racing operation, which became his very own passion project.

In fact, if it wasn’t for his daytime job on TV, we probably would’ve seen a lot more of Alex Trebek at the tracks. After purchasing his farm, there was a point in time where Alex owned about 40 horses and even had horses compete in the Kentucky Derby. Fitting in with his other famous fellows, Alex now had more than one reason to always attend.

Queen Elizabeth Has Owned Horses Longer Than She Has Been Queen

Being a racehorse owner longer than she has been queen, her majesty Queen Elizabeth is no stranger to the race tracks, especially the Kentucky Derby. From her toddler toys to the Royal Ascot racing stables, Queen Elizabeth has loved horses her entire life. Over the years, the queen has become a notable figure that would always attend equine events. Of course, the Kentucky Derby fell into the bracket of horsing events she would frequent since 2007.

Though none of her horses have competed in the Kentucky Derby, there’s nothing more the Queen loves than attending a good race. One can only imagine just how much she must have bet in the American races if it comes anywhere near to what she spends on her own stallions.

MC Hammer Is an Award Winning Racehorse Owner

His flashy dance moves, signature pants, and hit songs like “U Can’t Touch This,” are just a few things that the rapper MC Hammer has associated with his legacy. But surprise – this dance machine was amongst the many celebs that had a soft spot for the Kentucky Derby, mainly because his horses were associated with it.

Hammer established the Oaktown Stables, where he owned 19 thoroughbred racehorses. At the Kentucky Derby, he always felt like a megastar who belonged there, Especially since he had a horse named “Dance Floor” that competed in the 1992 race. And dressed to impress, he always made sure to wear the finest suits that showed that he was there for business, as much as pleasure.

Dylan Dreyer Says That the Kentucky Derby Is a Once in a Lifetime Event

Growing up in New Jersey, The Today Show host Dylan Dreyer wasn’t exactly familiar with the concept of horse racing. So when she was sent to cover the Kentucky Derby, she had no idea what she was getting into. Upon her arrival, it only took her a matter of minutes to be immersed in the event’s unique culture to understand that this was no ordinary rodeo; this was a once-in-a-lifetime event.

Ever since her first time covering the races, she’s made it a point to return each year for professional and personal reasons. From the endless mint juleps, party festivities, and fun fashion, it provides the perfect break from reality to submerge yourself in a weekend full of enjoyment. Five years later, and she still believes that anyone who gets the opportunity should definitely make it a point to attend the Kentucky Derby.

Tom Brady Makes Sure That the Kentucky Derby Turns Out to Be the Ultimate Boys Weekend for His Friends

Tom Brady is the epitome of the football sport – at least in our eyes. And he is now also known as THE party animal when it comes to the Kentucky Derby. Regarding this sporting event, it’s considered a yearly tradition for Tom to attend with a crew comprised of his other football teammates. This makes it the ultimate boys’ weekend while they don’t have spring training or a game to prepare for.

But what is it that really entices Tom Brady to appear at the derby year after year? Well, it’s not so much the actual event, but the pre-party gala that lures him in. Like anything else, there’s always a pre-party to the actual party. The pre-party that has become iconic for the Kentucky Derby is the Barnstable Brown Gala, which takes place the night before the race.

Kim Kardashian Loves to Be a Part of the Big Hat Fashion Fun

Since her first appearance at the Kentucky Derby in 2009, Kim Kardashian made sure that she would fit in with the required attire for the event. So, of course, she makes sure that she rocks the gaudiest and fashionable big hats for the occasion. Yea, clearly, Kim takes zero interest in the horses or racing elements of the derby; it’s strictly glamour and PR purposes for her to be there.

You can bet your bottom dollar that if there’s any high-profile event that involves some of the biggest names in the celebrity world, then at least one, if not all, of the Kardashian’s will be there. So obviously, Kim Kardashian has made it a point to show up to the races, but only if her hats will make as much of a statement as her appearance will.

Michael Jordan and John Salley Put Their Rivalries Aside in Honor of Living It up at the Kentucky Derby

Back in their prime, Michael Jordan and John Salley were known to be the fiercest competitors and rivals from the moment they stepped on the basketball court. And while they may have had a few altercations in their history, there was one event, and one event only, that kept them from being aggressive towards each other – and that, friends, is none other than the Kentucky Derby.

Well, except for the one incident where MJ’s security guard sucker punched Salley right in the gut – which was completely unwarranted – they never had an altercation at the derby. These athletes knew to keep business and pleasure separate and always loved to enjoy the Kentucky Derby for what it is – the best party that provides a break from the world.

Steven Spielberg Is Also a Racehorse Lover, Who’s Own Horse Placed at the Kentucky Derby

The acclaimed movie director and producer Steven Spielberg is yet another shockingly surprising character that took an interest in horse racing. Not only did he take a serious interest in several horses through investing in a prominent stable, he even co-owned a horse that would compete in the Kentucky Derby.

After learning the ropes of horse racing and what goes it takes to own your own horse, the horse that Steven decided to co-own not only made it to the Kentucky Derby back in 2003 but even made it in fourth place overall. And like Steven’s quirky personality, his horse, of course, had an even quirkier name. There’s no way you could ever guess it, so we have to tell you that the horse was actually called Atswhatimtalknbout. Seriously.

Gene Simmons Thinks That Betting on All of the Horses That Compete Is the Best Strategy…

He may be known as the famous bassist for the band KISS, but what he’s definitely not applauded for are his skills – or lack of – at the Kentucky Derby. Gene Simmons might be an incredibly talented musician, but he’s far from staying on the right track when it comes to how he spends his time at the races.

Lucky for us, this was even captured on television during an episode of Gene Simmons’ Family Jewels. After his wife had just lost a big bet she had placed, Gene professes to have no fear, as he had bet on every single horse that was competing. We’re no pros when it comes to this type of sport, but according to every piece of advice out there – this is exactly what shouldn’t be done.

Morgan Moses Never Misses a Derby Day, Thanks to Her Beauty Queen Status

You’ve seen her face before, but you probably aren’t too sure of her name. Miss Morgan Moses is more or less a C-List Celebrity when it comes to the Kentucky Derby, but that doesn’t mean you won’t find her on the guest list. Her semi-celeb status is all thanks to her basically being the face of every beauty pageant Kentucky has ever had, making her a local representative and permanent party goer to the Churchill Downs every year.

For Morgan, attending the Kentucky Derby isn’t just an option but a way of life. She grew up around the whole atmosphere, and in her own words, she “eats, sleeps, and breathes the Kentucky Derby.” From the ambiance to the fashion, to the list of high profilers in attendance – there’s nothing this beauty queen loves more than to be a part of it all.

Cynthia Bailey and Her Boyfriend Mike Hill Love to Bet on the Racehorses as Much as They Like to Have Matching Outfits

We’ve come to know her as a leading lady on The Real Housewives of Atlanta. But once a year, the world gets to know Cynthia Bailey for the high stakes she plays at the Kentucky Derby. Yup, this reality TV star loves nothing more than to test her luck and rock the country red carpet at the Churchill Downs.

Spotted with her boo Mike Hill, Cynthia had to make sure that, if nothing else, their headwear was not only fabulous but color coordinating. Additionally, the two even came close one year to winning the big race. They had wagered a fair amount of money on one horse that was in the lead for about 30 minutes until their horse was disqualified. They may not have made their mark on the tracks, but they sure did make a fashion statement.

Dannielynn Birkhead and Larry Birkhead Have Made the Kentucky Derby a Part of Their Family Tradition

Ever since she was three years old, Anna Nicole Smith’s daughter, Dannielynn Birkhead, and her father, Larry Birkhead, have never missed a Kentucky Derby. Starting in 2010, the father-daughter duo made attending this event a part of their own special family tradition. But it wasn’t until 2012 when Dannielynn decided to start fully embracing the derby style and started to don the fancy headpieces that the other women of the derby usually sport.

And if their tradition of always attending the derby wasn’t sweet enough, the fact that they always have color-coordinated matching outfits is so sweet it’ll give you a toothache. Even as a teenager, Dannielynn still loves to share the special occasion with her dad and is proud to have him by her side. This year, she was lucky enough to rock the fashion show competition in a turquoise Jovani pantsuit which led her to be the overall winner.

Jack Nicholson Likes to Be a Crowd Pleaser on Screen and on the Racetrack

We all know Jack Nicholson for his roles in accomplished films like One Flew Over the Cuckoo’s Nest, As Good As It Gets, and Something’s Gotta Give. If there’s one thing he knows how to do, it’s to command attention from the audience. And whether he’s on set or at a public event, he just can’t help from being the center of attention. Of course, the Kentucky Derby is no different for him.

One of his most famous derby debuts include when he escorted one of the horses and its co-owners on the track. As if he hadn’t already caused a commotion with the crowd cheering wildly at his appearance, he decided to stop mid-dirt, hold both his hands high and take an over-dramatic bow. Coincidentally enough, the horse he escorted was far from winning first place that year. But honestly, we don’t think he cared about it one bit.

Star Jones and Her Pooch Never Miss a Derby Weekend

For over eight years, Star Jones has made it a point to not only make an appearance at the Kentucky Derby but to make sure everyone knows that she’s there. And while she’s had different husbands over the years, her one constant partner to the social event of the spring has always been her trusty pup, Mimi.

While most people may think that Mimi serves as a fashion accessory to complete Star’s outfit, she serves a much more important role outside of completing her dog mama’s look. Star’s little pooch is actually a service dog that helps keep her calm in the midst of chaos. So for a busy, bustling event like the Kentucky Derby, it’s actually essential that Mimi tags along with her fur mama. Together, they are showstoppers for the paparazzi.

Wes Welker Has Been in the Business of Owning Race Horses for Over 10 Years

He’s known for his major accomplishments not only on the football field, but also on the race track. Wide receiver Wes Welker is an athlete through and through, and whether it’s in the NFL or professional horse racing, he’s considered a sporting star across the board. When he took up the likes of owning race horses, it was to be assumed that he would become well known in this sporting field as well.

For over ten years, Wes has owned racehorses that have constantly competed in the Kentucky Derby. Not only is this event the highlight of everyone’s social calendar, but the Kentucky Derby also means business for Wes. And as much as he loves to win, he loves to show off to his peers about his winnings even more.

Tori Kelly Makes It Big by Earning the Honor to Sing the National Anthem at the 2021 Kentucky Derby

The singer/songwriter Tori Kelly is known for having a big voice. Well, finally, she’s gained enough recognition and respect for her talent that she was the chosen one to sing the national anthem at the 2021 Kentucky Derby. Trademarking this as her first-ever derby, she planned to go all out for the event, big hat and fancy dress included.

When discussing her outfit plans, Tori even said it would be “crazy for me not to fully embrace everything that comes with it.” And while this may have been her first rodeo, it certainly won’t be her last, all thanks to the memorable time she had this year.

Nick and Vanessa Lachey Love to Slay and Play at the Kentucky Derby

Unlike his wife, Nick Lachey has a longstanding reputation for never missing a single Kentucky Derby. From the days he was peaking as a boy band heartthrob in 98 Degrees, it became “a thing” for all of the most popular boy band artists to attend this unique event. Since the early 2000s, Nick started going and just never stopped. Thankfully, his Missus, Vanessa, was reeled into the derby magic as well.

While Nick likes to attend for the partying scene, Vanessa is much more into the fashion statements that can only be made at the Kentucky Derby. She loves to wear chic, classic, timeless outfits that, while are more than appropriate for the derby, we wouldn’t mind seeing these on the red carpet either.

Bo Derek Is Heavily Involved in the Horse Racing Industry

Famous actress Bo Derek is known for having a permanent invitation to the Kentucky Derby. While she may not own any horses that compete on the racetrack, she’s widely respected in the equine world as much as she is in Hollywood.

Though we’re not sure why she keeps an apparent separation between her involvement in owning, betting, and supporting the sport – it’s enough that guarantees her annual attendance to the Churchill Downs. As a matter of fact, Bo is a member of the California Horse Racing Board.

Ashton Kutcher Like to Dress the Part He Plays When Betting at the Churchill Downs

Breaking out his best bow tie and vest for the occasion, Ashton Kutcher is another hunky star that you can expect to see at the Churchill Downs in any given year. And as you can tell from the picture below, he takes the sport very seriously. Focused intently on the track, it’s clear he’s silently stewing over which horse will take the prize and if it will result in him receiving any prize at all.

Donning a very event-appropriate newsboy cap, Ashton arrives in style to the derby. As they say, when you look good, you feel good; when you feel good, you play good. We can only wonder just how much Ashton throws down at the racetrack every year, but we’re sure if he were a winner, then this answer wouldn’t be so unknown to us.

Mary White Only Attends the Kentucky Derby Because of the Barnstable Brown Derby Eve Gala

Mary White is best recognized as one of the founding members of the legendary singing group The Supremes. But better yet, she’s a legend in herself for being an annual regular to the Barnstable Brown Derby Eve Gala that happens every year the night before the Kentucky Derby. It’s just a night of glamour that this diva refuses to miss out on.

Like many other stars, the party scene is quite the lure for even the unlikeliest of attendees to be drawn to the great state of Kentucky for their claim to fame. But Miss Mary finds the whole concept dazzling and loves to surround herself with the southern charm and elite guest list for those that attend the famous gala. She may stay the weekend and attend the Kentucky Derby, but it’s the party that really draws her in.

Shailene Woodley and Her Crew Love to Get Dressed Up to Get Down N Derby

We must tip our hats to Shailene Woodley and her crew, as they totally made a statement at the 2021 Kentucky Derby. According to her bestie who Instagrammed the following picture, the caption said it all. Here they are, as they were ready to get “Down N Derby.” And that, they did.

Although the grand gala that usually takes place the night before the race was canceled, that wasn’t going to stop famous actress Shailene and her slew of friends from living their best lives at the Kentucky Derby. They were especially committed since they were cheated out of attending the 2020 event, as the pandemic had canceled it – along with everything else. But have no fear, the motley crew arrived in style and made sure to make it an unforgettable derby day.