THE 5 GREATEST CELEBRITY WHISKEY WINS

“The Derby Isn’t a Race—It’s a Religion.”

I grew up just east of Louisville, Kentucky, where the scent of blooming magnolias and charred oak meant one thing—Derby season was here. And where I come from, the Kentucky Derby isn’t just a horse race. It’s Christmas in seersucker, with bourbon on the breeze and pride in every porch flag.

We didn’t miss it. Not once.

My granddaddy—God rest him—was a retired cooper who could name every Derby winner from Citation to Secretariat. Come race day, he’d dust off his old transistor radio, pour us some sweet tea laced with “back porch bourbon,” and holler at those horses like he trained ’em himself. Whether the crops were good or lean, May felt like money in the soul.

And tomorrow? I’ll be doing the same—glass in hand, heart racing, calling every turn like he taught me.

Because around here, whiskey and the Derby go together like fast horses and floppy hats.

So in the spirit of champions—and in honor of the Run for the Roses—let’s talk about the celebrity whiskeys that didn’t just show up for the fame. These five bottles ran with the big dogs… and they earned their garland. 🏇🥃

🥇 #1 — The Secretariat of Celebrity Whiskeys

🏆 Heaven’s Door by Bob Dylan

This one doesn’t just lead the pack—it laps it. Just like Secretariat’s unforgettable 31-length Belmont win, Heaven’s Door is the undisputed juggernaut of the celebrity whiskey world.

Crafted in collaboration with Cascade Hollow Distilling Co. (yes, the same legendary folks behind George Dickel), this bourbon is a poet’s passion project—not a vanity label. It’s aged in new American oak barrels, finished in toasted French oak, and left non-chill filtered to preserve every bit of soul.

Tasting Notes:

• 🥖 Warm brioche

• 🍯 Honey drizzle

• 🪵 Toasted oak and spice

• 🍏 Baked apple finish

Heaven’s Door isn’t just Dylan’s name on a label. It’s his songwriting spirit bottled and barrelling toward greatness.

Purchase here:
👉 Heaven's Door Straight Bourbon Whiskey – $47.99

🥈 #2 — The Seabiscuit

🏆 Uncle Nearest x Wesley Snipes

This collab isn’t a cash grab—it’s a cultural tribute. Wesley Snipes partnered with the legendary Fawn Weaver and the legacy of Nearest Green, the formerly unsung Black distiller who taught Jack Daniel the ropes.

The result? A whiskey that runs deep—historically, emotionally, and flavorfully. Rich and robust, just like Seabiscuit himself, this pour proves that the most powerful stories are often the ones waiting to be rediscovered.

Tasting Notes:

• 🌽 Cornbread and brown sugar

• 🍫 Dark cocoa

• 🌰 Nutmeg warmth

• 🪵 Oak-heavy mid-palate

It sips like reverence. It finishes like redemption.

Purchase here:
👉 Uncle Nearest 1856 Premium Aged Whiskey - $59.99

🥉 #3 — The Seattle Slew

🏆 Wild Turkey Longbranch by Matthew McConaughey

Alright, alright, alright. This pour is as charismatic as its co-creator. McConaughey teamed up with Wild Turkey’s Eddie Russell to produce a bourbon refined with Texas mesquite charcoal.

It brings together Kentucky tradition and Texas swagger in a bottle that’s approachable, yet nuanced—like Seattle Slew, the only undefeated Triple Crown winner.

Tasting Notes:

• 🌽 Sweet corn

• 🌰 Toasted pecan

• 🔥 Hint of mesquite

• 🥧 Brown sugar on the back end

This one’s got range. A porch-sipper that holds up at a poker table.

Purchase here:
👉 Wild Turkey Longbranch Bourbon Whiskey – $44.99

🏅 #4 — The Affirmed

🏆 Blackened by Metallica

This whiskey doesn’t whisper—it wails. Blackened is the unholy marriage of sound engineering and traditional aging. It’s a blend of bourbons and ryes from across North America, aged with Metallica’s actual music vibrating through the barrels.

Wild? Maybe. But it works. Affirmed didn’t need flash to win—he just delivered. So does this.

Tasting Notes:

• 🍒 Dried cherry

• 🍂 Smoked maple

• 🍬 Burnt sugar

• 🔥 Clove and heat

Blackened is bold, loud, and unforgettable. Like a power chord in a Glencairn glass.

Purchase here:
👉 Blackened American Whiskey – $44.99

🏵 #5 — The Zenyatta

🏆 Sweetens Cove by Peyton Manning & Andy Roddick

Zenyatta was elegance in motion—and so is this pour. Born from a golf course with a cult following, Sweetens Cove is carefully curated by Marianne Eaves, the first woman master distiller in Kentucky since Prohibition.

She crafted a bottle that’s both refined and complex. It’s not here for the spotlight—it’s here to win quietly. One sip and you'll understand.

Tasting Notes:

• 🍑 Peach cobbler

• 🍬 Vanilla bean

• 🥥 Toasted coconut

• 🪵 Soft oak finish

Smooth, subtle, and worth savoring. Just like the great mare herself.

Purchase here:
👉 Sweetens Cove Tennessee Straight Bourbon Whiskey Aged 13 Years – $179.99

🥃 THE WEEKLY POUR

Spotlight: Heaven’s Door by Bob Dylan

Heaven’s Door sits at the top of the podium—and for good reason.

🔍 Distillery Highlight: Cascade Hollow, Tennessee

Home to the George Dickel line, Cascade Hollow knows how to age whiskey in climates that whisper instead of shout. Barrels here breathe through hot Southern summers and frosty nights, letting the oak do its dance.

Heaven’s Door takes that slow burn and adds artistry. The French oak finishing rounds out the bourbon’s spice with buttery smoothness. Every release is hand-batched and curated. No shortcuts. No filler.

Just like Dylan’s music—it’s layered, thoughtful, and full of soul.

🍹 THE ART OF MIXING

“Southern Refrain” – A Derby Day Sipper

Ingredients:

• 2 oz Heaven’s Door Bourbon

• ¾ oz peach liqueur

• ¾ oz lemon juice

• ¼ oz honey syrup (1:1 honey + water)

• 2 dashes Angostura bitters

• Garnish: mint sprig and lemon wheel

Directions:
Shake with ice. Strain over a big cube. Garnish and serve.

Bright. Boozy. Balanced. Just like a good Derby pick.

🧠 BIG LESSON OF THE WEEK

Don’t Let the Myth Fool You—True Greatness Comes in Strides

A lot of folks think Secretariat won the Kentucky Derby by 31 lengths. Not so. That legendary margin happened at the Belmont Stakes. But in the 1973 Derby? Secretariat did something even more remarkable—he came from dead last.

Through the first quarter mile, he trailed the entire field. Cool, calm, and calculated. By the half-mile, he started his charge. And down the final stretch, he pulled ahead like he had rocket fuel in his veins, crossing the line in 1:59 2/5—a track record that still stands.

He didn’t just win. He ran every quarter mile faster than the last. A negative split. The mark of a master.

The runner-up that day? Sham. A hell of a horse in any other year. But this wasn’t just any year. And Secretariat wasn’t just any horse.

Same goes for great whiskey. The best pours don’t bolt out the gate with flash and hype. They bide their time. Build complexity. Earn their place. These celebrity bottles didn’t bet on fame—they bet on the craft. And it shows in every smooth, satisfying sip.

🥂 FINAL TOAST

“To the long shots who trained hard, the legends who aged well, and the bottles that remind us greatness takes time.”

🧓 WEEKLY PROVERB

“Never bet on the label—bet on the barrel.” 🥃

📚 POUR IT FORWARD

🔥 Grab my new book:
“Whiskey, History & 5 Damn Good Stories to Share Over Your Next Pour”

If you liked this roundup, you’ll love the stories I put together of rebels, outlaws, and whiskey angels inside. Pour one and dive deep.

🔁 WHAT TO DO NEXT

💬 Drop your favorite celeb whiskey in the comments
🌟 Star this post if you've got one on your shelf
📤 Share with a friend who still thinks all celeb whiskey is junk
📚 Save this for your next bottle hunt

🛢 Until next time—keep your stories neat and your pours smooth.

Ethan “Neat” Whitmore
Your friendly neighborhood whiskey whisperer

P.S. Next week: I'm sharing the 3 American distilleries making world-class whiskey with zero fanfare. You’ll want to be the friend who “discovered it first.”