Double Oak Bourbon Showdown: JYPSI Tribute vs Woodford Double Oaked vs Pursuit United
Double Oaked Bourbon
Double Oak Showdown: JYPSI Tribute, Woodford Double Oaked & Pursuit United
Welcome back to Tortured Bourbon, where Heather and B dig deep into America’s favorite brown water with equal parts science, sarcasm, and questionable decision-making. For this episode, we turned our attention to the world of double-oaked bourbons—those rich, caramel-packed pours known for giving you a second helping of oak influence, dessert sweetness, and warm, toasty flavor.
If you missed the episode, you can watch it here:
👉 https://youtu.be/iPnMOMtBBrk
🪵 What Does “Double Oaked” Even Mean?
Double-oaked bourbon is exactly what it sounds like:
A bourbon aged in two separate new-oak barrels.
The first barrel works its usual magic—caramelizing sugars, adding vanilla, spice, and structure.
The second barrel (often more toasted, lightly charred, or seasoned differently) adds:
richer caramel
warm brown sugar
toasted marshmallow notes
deeper oak complexity
dessert-like sweetness
Think of it as bourbon with a second chance at flavor.
🥃 THE CONTENDERS
Whiskey JYPSI – Tribute
Distiller/Producer: Outsider Spirits
Proof: 86
Finish: Re-barreled in new American oak for 3–6 months
MSRP: $40
Nose: Caramel, toasted vanilla, cherry, baking spice, honeycomb, charred marshmallow
Palate: Dark chocolate, cinnamon, apricot, roasted nuts, tobacco
Finish: Long, warm, sweet oak
Overall: An easy-sipping double-oak with classic marshmallow-caramel charm.
Woodford Double Oaked
Distiller/Producer: Woodford Reserve
Proof: 90.4
Finish: Deeply toasted, lightly charred second barrel
MSRP: $31.95
Nose: Honey, chocolate, marzipan, dark fruit
Palate: Vanilla, hazelnut, apple, warm spice
Finish: Creamy and long, honeyed apple
Overall: A bourbon staple—rich, silky, and endlessly approachable.
Pursuit United – Double Oaked
Distiller/Producer: Pursuit Spirits
Proof: 108
Finish: French oak staves (36-month seasoned)
MSRP: $70
Nose: Butterscotch, toffee, toasted marshmallow
Palate: Vanilla custard and warm butterscotch
Finish: Cinnamon-spiced pears, toasted oak
Overall: High-proof elegance with beautiful fruit-and-oak balance.
🥊 FINAL THOUGHTS
Each double-oaked bourbon brings something different to the table:
JYPSI Tribute is your mellow, sweet, everyday sipper.
Woodford Double Oaked remains the gold standard for rich, dessert-leaning bourbon.
Pursuit United delivers complexity and proof-driven character with a French oak twist.
Whether you’re new to double oak or already deep in the toasted-barrel rabbit hole, this lineup offers something for every palate.
Watch the full tasting and our official Tortured Bourbon ratings here:
👉 https://youtu.be/iPnMOMtBBrk
Cheers, y’all.
Stay tortured. Stay thirsty.
