The Double: Jay Cutler and Brandon Try Five Bottles of Whiskey with Southern Whiskey Society’s Chris Thomas

by Chris Haney

This week on Outsider’s The Double, hosts Jay Cutler and Brandon Chesbro are bringing in another special guest as Southern Whiskey Society’s Chris Thomas joins the show. Thomas selected five bottles of whiskey for the trio to taste, and there’s not a bad one in the batch.

Thomas and Southern Whiskey Society had a big weekend since their annual whiskey event took place on Saturday. On August 6th, the 2022 Southern Whiskey Society event took place in historic Franklin, Tennessee where they celebrated some of the best food and whiskey in the South. Now, Thomas is bringing a portion of those celebrations to The Double as he shares some great whiskey with Jay and Brandon.

Early on as the three met, Jay asked Chris how he got into whiskey collecting. The whiskey connoisseur and a friend really dived into the spirits back in 2010. Ten years later in 2020, Thomas shared that he realized he had accumulated around 1,700 bottles of whiskey. That astonishingly large number is not a misprint.

Thomas arranged the chosen five bottles the group is testing out from low proof to high proof. In this episode of The Double, we’re testing out a classic from Woodford Reserve and a special rye from Jack Daniel’s. We’ve also got two more from one of Outsider’s favorite micro-distilleries just outside of Nashville from Leiper’s Fork Distillery. Plus, the guys are finishing things off with a unique bottle from Rare Character Whiskey. So let’s get to it and taste some whiskey.

Woodford Reserve Kentucky Straight Bourbon

  • Color: Clear, brilliant honey amber
  • Nose: Heavy with rich dried fruit, hints of mint and oranges covered with a dusting of cocoa. Faint vanilla and tobacco spice
  • Taste: Rich, chewy, rounded and smooth, with complex citrus, cinnamon and cocoa. Toffee, caramel, chocolate and spice notes abound
  • Finish: Silky smooth, almost creamy at first with a long, warm satisfying tail
  • Proof: 90.4 Proof, or 45.2% Alcohol by Volume
  • MSRP: $39.99

First up, we’ve got a classic you can never go wrong with – Woodford Reserve’s Kentucky Straight Bourbon.

“It’s smooth. Easy drinking, little burn” Jay said of the Woodford Reserve.

“Phenomenal,” Brandon added. “It’s got that perfect amount of like that little spice right on the front end.”

“Rich, sweet. And it’s low proof – easy drinking,” Chris said of the bourbon. “Vanilla. I mean it’s an iconic brand. And I feel like you have Jack Daniels, and then you have Woodford Reserve.”

Jack Daniel’s Single Barrel Rye

  • Color: Amber
  • Taste: Complex flavors of ripe fruit with light toasted oak notes
  • Finish: Rich with spice and a pleasant lingering finish
  • Age: Around 4 years
  • Proof: 94 Proof, or 47% Alcohol by Volume
  • MSRP: $49.99

For our second whiskey of the day on The Double, Chris is treating Jay and Brandon to a special rye whiskey from Jack Daniel’s. Chris asked Jay what he thought about the famed distillery before they tried the rye. Jay admitted he thinks most people assume Jack Daniel’s is a lower tier spirit these days. However, Chris shared that he thinks the distillery is making “some of the best single barrels out there right now.” High praise indeed.

“It’s just so different form a bourbon,” Brandon said of the rye whiskey.

“The more we keep drinking these ryes, the more I like them more and more,” Jay said.

“Rye whiskeys have a special place in my heart,” Chris agreed.

“Me too,” Jay added.

Leiper’s Fork Tennessee Whiskey Experimental Maple Barrel (Distillery Exclusive)

  • Specifications & Characteristics: N/A
  • MSRP: $N/A (*Only sold in Leiper’s Fork Distillery’s gift shop)

Next up on the menu is Leiper’s Fork Distillery‘s first-ever experimental release, which is a blend of 10 single barrels at cask strength. The distillation process then ends with the spirit living in a barrel formerly used for maple syrup for about 65 days. The guys are in for a treat as they taste the Leiper’s Fork Tennessee Whiskey Experimental Maple Barrel.

Unfortunately for readers, since this is a limited production run, it’s only sold in Leiper’s Fork Distillery’s gift shop. There’s not much information on the specifics of the spirit online, so you’ll have to visit the distillery yourself to try it out and learn more. According to the guys, it’s well worth the trip about 30 minutes outside of Nashville.

“This is a conversation piece,” Brandon said about the experimental whiskey.

“Once you taste it, the maple is just a hint,” Jay shared.

“Yea, it’s so daggum good,” Chris says on The Double. “And it’s just different.”

Leiper’s Fork Single Barrel Cask Strength Whiskey (Distillery Exclusive)

  • Color: Dark amber
  • Nose: Rich, sweet and sticky. Dark dried figs, Hershey kisses chocolate and honey
  • Taste: Notes of corn, vanilla, toffee, and oak
  • Age: 5 years, 9 months old
  • Proof: 110 Proof, or 55% Alcohol by Volume
  • MSRP: $99 (*Only sold in Leiper’s Fork Distillery’s gift shop)

While this particular spirit isn’t quite as rare as Leiper’s Fork Distillery’s experimental whiskeys, it’s still only sold in their gift shop. The guys loved this one as well as they all sang the praises of not only this whiskey but all of the distillery’s spirits.

“I think Leiper’s Fork is putting out some of the best whiskey in the country right now. It’s like a chocolate malt,” Chris said on The Double.

“I get that,” Jay agreed.

“I can drink this all day,” Chris continued. “I’d be in trouble, but I could drink this all day.”

Rare Character Whiskey Single Barrel Straight Bourbon

  • Color: Light amber
  • Taste: Sweet and delicious, with oaky notes of vanilla and cherry
  • Mash Bill: 60% corn, 36% rye, 4% malted barley
  • Age: 5 years, 7 months old
  • Proof: 122.6 Proof, or 61.3% Alcohol by Volume
  • MSRP: $87

For the last tasting of the show, Chris is introducing Jay and Brandon to a distillery they don’t know much about. Rare Character Whiskey works with some of the top distillers in the nation to produce “unique selections tailored to each of our customers and partners.” The distillery’s website wasn’t lying with that description considering the guys said they’ve never tasted anything like it before.

“It’s just different. To me it’s just so interesting,” Chris commented about the unique whiskey.

“That one’s wild,” Jay said on The Double. “It’s almost got like a rum feel to it.”

“Yea, I don’t disagree with that,” Chris agreed.

“I’m still getting some of that florally (smell),” Brandon said as they started to wrap things up. “Well, this was fun.”

“Yea, it was a blast. I appreciate it,” Jay said to Chris.

“Thank you. Easy, easy. Now I’m gonna have to finish these off,” Chris shared as things came to a close.

Make sure to tune in next week as Jay and Brandon taste more whiskey on Outsider’s The Double.