Shaboozey’s new album has been heating up the summer. With his lead single, “A Bar Song (Tipsy)” reaching the number 3 position on the Billboard Hot 100 last week and his album Where I’ve Been Isn’t Where I’m Going debuting in the top 5 of Billboard’s album charts as well as topping the Independent Album charts this week, now is the best time to get into the Virginia hit maker’s unique blend of country, hip-hop, and heartbreak. While those are the three primary ingredients in Shaboozey’s chart-topping album, it’s impossible to ignore how ever-present booze is on the project’s 12-song journey.
Shaboozey’s star has been on the rise since releasing “Start a Riot” with Duckwrth on the Spiderman: Into The Spiderverse soundtrack back in 2018, and it reached a fever pitch when he collaborated with Beyoncé on her smash-hit Cowboy Carter album earlier this year. With all of that hype following Shaboozey and the niche he’s carving in the alt-Country music movement, it’s clear that he’s garnered a lot of attention outside of traditional Country music circles…including in the whiskey world.
So, to help you get into the genre-redefining album, we thought it would be a great idea to give you the perfect whiskey list to pair with every song on Where I’ve Been Isn’t Where I’m Going to help enhance your listening experience. After all, with Shaboozey reaching for a drink throughout the album, why shouldn’t you join along? It’s a boozy, alcohol-infused ride over the album’s dozen songs, and if you want to fully appreciate it all, then this is the perfect list for you.
Grab a glass, sit back, and prepare to get tipsy with the surprise hit album of the summer!
1. “Horses & Hellcats” with George Dickel Tennessee Bottled in Bond Whisky
ABV: 50%
Average Price: $50
The Song:
The album’s intro opens with guitar strumming and horses braying, setting the stage perfectly for Shaboozey’s unique soundscape. Embracing his love for the open country and the horsepower of Hellcats, he notes that if you’re looking for him, he’ll be “out in Tennessee,” which is exactly where we’ll go for our first whiskey recommendation.
The Whiskey:
George Dickel is one of the best-selling American whiskey brands on the planet, so it makes perfect sense to reach for one of their best (and one of their most widely available) bottles to pair with “Horses & Hellcats.” George Dickel Bottled in Bond is released annually, and this year’s version, made with a mashbill that’s 84% corn, 8% rye, and 8% malted barley, is matured for 13 years.
Tasting Notes:
Nose: Look for warm brown sugar, sticky maple syrup, and fruity notes like stewed red apple and ripe bananas when you catch a whiff of this intoxicating whiskey. Adding to the cowboy vibes, a smoky undertone goes well with the mellow oak aromas here. Lastly, there’s a touch of milk chocolate sweetness, which gives this whiskey the impression of being artfully aged.
Palate: On the palate, expect to taste toasted pecans with some subdued brown sugar as the maple syrup aroma notes become more distinct in the mouth. The flavor of bruised bananas and a faint bit of wet tobacco, nutmeg, and cornbread also stand out. The mouthfeel is surprisingly rich and robust despite being only 100 proof, which will make you feel like you’re “pushing (those) horses to the limit” while Shaboozey croons about hitting high speeds in his Hellcat.
Finish: On the finish, there’s a rising impression of leather, and more fruit comes into play as a bit of waxy fig comes to the fore, along with a few shakes of allspice.
Bottom Line:
If you’re out in Tennessee, this is one of the quintessential whiskeys that you simply have to try. This is George Dickel Tennessee Whisky at its best, with a perfect proof point for enjoying a high-octane ride (from the passenger seat) as well as turning up at home while you get into this infectious intro.
2. “A Bar Song (Tipsy)” with Jack Daniel’s Tennessee Whiskey
ABV: 40%
Average Price: $28
The Song:
Shaboozey’s breakout single is the perfect encapsulation of his style. Equal parts boozy and Country, with an interpolation of J’Kwon’s “Tipsy” thrown in for good measure, signaling his hip-hop appreciation, this is simply a song that everyone can, and is, enjoying right now.
The Whiskey:
Look, if Jack Daniel’s Old No. 7 needs an introduction, then you probably shouldn’t even be here. I mean, it’s only the most recognizable bottle of whiskey in the world! Sure, ubiquity in itself isn’t a signifier of quality, but with Shaboozey mentioning it by name and an ABV (and price point) that makes it suitable for taking shots at the bar, there’s no better whiskey to pair with the album’s lead single.
Tasting Notes:
Nose: Maple candy, buttered popcorn, and banana pudding come tumbling out of the glass to greet the nose, along with a touch of red pepper. That maple candy note is due to the Lincoln County Process, a maple charcoal filtration process that all Tennessee whisky undergoes by law.
Palate: Banana pudding is again present on the nose, with some faint vinegar-based BBQ sauce notes and some gentle oak tones. A bit of maple candy provides the last oomph of flavor on this easy-sipping pour.
Finish: The finish is where you’ll find a slight flourish of black pepper baking spice, but overall, it’s full of those maple syrup notes that reverberate throughout the nosing notes and the palate profile.
Bottom Line:
For a lot of people, Jack Daniel’s Old No. 7 was probably their introduction to whiskey, just like “A Bar Song (Tipsy)” is probably a lot of folks’ introduction to Shaboozey. Because of that, it’s hard to imagine a better pairing throughout the entire album — this one just makes perfect sense.
3. “Last of My Kind” feat. Paul Cauthen with Still Austin Ruby Red Port Barrel Finished Straight Rye Whiskey
ABV: 54%
Average Price: $100
The Song
“Last of My Kind” is a swaggering, self-confident song featuring Paul Cauthen, where Shaboozey thumbs his nose at the law and fully embraces the cowboy ethos of self-reliance. For his part, Paul Cauthen notes that sometimes in this world, you’ve “got (to) get it if you want it, keep the fire burnin’ inside,” and if he isn’t talking about allocated whiskey, then I don’t know what that line could better describe.
The Whiskey:
The limited edition whiskey we’re going with for this song comes from Texas, just like Paul Cauthen, and it sold out quickly online because, true to the song’s title, it’s the last of its kind. A 100% rye whiskey, aged for 4 years, then finished for 8 months in Ruby Red Port barrels, this allocated whiskey is a one-and-done expression from the highly acclaimed Still Austin Distillery.
Tasting Notes:
Nose: Mulled wine, dried dates, sweet pastry, and spiced cranberry jam make up the nosing notes on this whiskey. Clearly, the Ruby Red Port has a strong influence here.
Palate: The full-bodied palate on this rye whiskey is accented by flavor notes like chocolate-covered raisins, fresh clove, pumpernickel toast, and fresh figs.
Finish: The finish on this whiskey is marked by cinnamon, cocoa powder, & stewed wild berries.
Bottom Line:
In a whiskey world where so many brands harp on their allocated expressions being “limited,” the truth is that few of them actually deliver on that premise. For this Ruby Red Port expression, Still Austin has truly released a whiskey that is the last of its kind, with no future plans to re-release the distillery-exclusive bottling. That’s exactly what makes it the perfect pairing here.
4. “Anabelle” with Four Roses Small Batch Select
ABV: 52%
Average Price: $60
The Song:
In this song of heartbreak, Shaboozey recounts a dark cloud of a lover who took the affection that he gave her and poured it into another man. If that doesn’t make you want to pour a glass of whiskey, I don’t know what it’ll take. Despite the fact that those circumstances left Shaboozey salty, penning some spicy lyrics to hide his heartbreak, we think you’ll need something complex and ultimately sweet to counterbalance all those emotions.
The Whiskey:
Four Roses Small Batch Select is a special blend that utilizes 6 of Four Roses’ ten recipes. Officially launched back in 2019, this ongoing expression is part of Four Roses’ core lineup and is perhaps the best widely available example of the brand’s blending prowess.
Tasting Notes:
Nose: The nose is full of baking spices, ranging from nutmeg and black pepper to clove and thyme, but those baking spice vibes are quickly followed by a slightly floral aspect (yes, think roses) as well as some rich red berry tones like dried strawberries and ripe cranberries.
Palate: The palate is an intriguing ride as it again follows the same path of transitioning from ample baking spices to sweet, fruit-forward flavors. The baking spices are most prominently led by black pepper and thyme here, while the red berries come in at full force as this pour transitions to the finish, riding a robust mouthfeel to the back of the palate.
Finish: The finish finds a fresh punch of black pepper coupled with a touch of honey and mulled wine, offering a nice climax of balance that is both lengthy and mellow.
Bottom Line:
The complex interplay of flavors on this whiskey makes it the perfect pairing for “Anabelle,” which features Shaboozey contending with conflicting feelings about his jilted lover. As he hopes she’s happy with the one she chose, you’ll be happy that you chose Four Roses Small Batch Select instead of looking for revenge.
5. “East of the Massanutten” with Westward Barrel Strength Single Malt Whiskey
ABV: 62.5%
Average Price: $100
The Song:
“I know that out there’s a land full of dreams, with milk, gold and honey, just waitin’ for me. So I’ll pack mе a little duffle, skip the goodbyеs and leave, ’cause East of the Massanutten, there’s nothin’ for me.” The chorus on “East of the Massanutten” expresses the yearning for a place that may or may not actually exist, but the yearning is part of the point. As is the realization that remaining stagnant and staying in place won’t get you what it is you’re pining for. Thus, Shaboozey turns westward, which is why our next whiskey is the perfect match for this song.
The Whiskey:
Westward’s Cask Strength offering is the pinnacle of their core lineup in that it offers their flagship whiskey as unfettered as you can hope for, short of theiving it from a barrel yourself. Made with 100% malted barley using only Pacific Northwest grains, this whiskey is perhaps the truest representation of the region you’ll find.
Tasting Notes:
Nose: Plums and cherries dance on the nose along with an undercurrent of malted chocolate, honey, and thyme. It’s a bold, fruit-forward bouquet that’s further buoyed by slightly burnt wheat toast and black pepper.
Palate: The silky mouthfeel of this whiskey leads to the introduction of black cherry, redcurrant, plum flesh, and black pepper on the palate. At midpalate is where honey sweetness simply bursts and fans out over the tongue with malted chocolate and oak, highlighting the transition to the finish.
Finish: The finish is full of fresh hazelnuts, more malted chocolate, and well-aged oak. Black pepper spice kicks in at the end as this lengthy finish slowly undulates away, making it a pour you’ll enjoy long after the last sip.
Bottom Line:
Sure, east of the Massanutten might not have anything left to offer Shaboozey, but heading Westward has plenty to offer you. Westward’s Cask Strength expression is bursting at the seams with flavor, and with the American Single Malt category sitting on the precipice of being a legally recognized category, it’s also full of promise for the future.
6. “Highway” with Angel’s Envy Cask Strength Rye Finished in Sauternes & Toasted Oak
ABV: 57.2%
Average Price: $450
The Song:
Another story about love lost, but rather than reacting with spite, this one is full of regret, with Shaboozey acknowledging that he should’ve been a better man. It’s a song about acceptance, searching for a long time for something that you may never find, and having to make peace with that. The second verse goes, “Since you stopped ridin’ shotgun, I ain’t been myself, goin’ out, lookin’ for a good time, but I’m goin’ through hell, got Jesus on the hotline sayin’, “You need help” put the liquor on the shelf, tell the devil, “Farewell.” That sets the stage perfectly for our next pairing…
The Whiskey:
Angel’s Envy Cask Strength Rye takes all of the best parts of their flagship rye offering but ratchets the flavor up several notches. While the brand’s standard rye is finished in rum casks, for this new Cask Strength offering, this Indiana-sourced rye is finished in Sauternes and Toasted Oak casks.
Tasting Notes:
Nose: The influence of the Sauternes casks leaps off the nose of this whiskey, with golden raisins, honey, and sweet mint leading the way before rye spice flares up on subsequent whiffs.
Palate: The syrupy mouthfeel is the first thing you’ll notice about this pour as golden raisins, white chocolate, rye spice, and black pepper begin to prickle your tongue as the viscosity fades away. There’s also a bit of marshmallow and gentle oak tones brought forth by the toasted casks.
Finish: The finish is slightly drying, but the flavor of golden raisins, black pepper, and toasted oak makes it through the end as it leaves a sweet impression, and it grips your palate for minutes after your last sip.
Bottom Line:
Change is life’s only constant, and accepting those changes can be one of life’s biggest challenges. However, it’s quite easy to make your peace with Angel’s Envy’s new Cask Strength Rye, which changes the formula of their flagship in a way that benefits the bump in proof and provides even richer nuance to appreciate. As you accept the mistakes you’ve made in life, you’ll need something with a sweet finish to remind you that it all gets greater later.
7. “Let It Burn” with George T. Stagg Kentucky Straight Bourbon Whiskey
ABV: 67.5%
Average Price: $1,300
The Song:
“Let It Burn” contends again with doubt, lost love, and acceptance as Shaboozey urges the listener to “throw the memories in the flames” and “see the gold in the red, new horizons.” It’s a hopeful song but one that also acknowledges the pain that can come with having to turn over a new leaf.
The Whiskey:
George T. Stagg is the perfect pairing for this song because it’s perhaps the most quintessential “fiery” pour of bourbon on the market. For 2023’s George T. Stagg, its 135 proof will surely burn a bit, but boy, does that high heat feel so good…
Tasting Notes:
Nose: Black cherry, rich oak, and Aleppo red pepper flakes make an immediate impression on the nose of this whiskey out of the glass. Throw in notes of molasses, brown sugar, and faintly mesquite aromas which all add challenging layers to the complexity of this high-octane pour.
Palate: Each sip opens with the syrupy sweetness of cocktail cherries but is then bolstered by the addition of leather, cinnamon, and charred red peppers. The mouthfeel of 2023’s George T. Stagg is exceptionally viscous and packs a proofy punch which, once it settles down, serves to introduce a broad range of robust flavors.
Finish: The finish contains a faint bit of smokiness and barrel char to go with a bold flourish of black pepper and toffee. Each taste lingers long after the last sip. That said, this is a bourbon that truly rewards extended savoring.
Bottom Line:
“Let It Burn” is a song that hopefully deals with the need to embrace change, using fire as a metaphor for fresh starts and espousing a belief in a “golden lining” following the flames. If there’s a single bourbon that will cause you to feel the burn in the best way possible, it’s George T. Stagg.
8. “My Fault” feat. Noah Cyrus with Starlight Double Oaked Bourbon
ABV: 51.5%
Average Price: $50
The Song:
In “My Fault” with Noah Cyrus, Shaboozey can be found commiserating with a friend on the verge of giving up. He takes turns blaming himself and the universe for the pain while Noah Cyrus chimes in that it might be easier to begin forgetting the memories. It’s a song where, again, bourbon is mentioned, but the sobering subject matter is heartfelt and takes center stage here.
The Whiskey:
This double-oaked variation on Starlight’s flagship bourbon is bottled at a higher proof (103) and undergoes a secondary cask maturation, which adds depth to their standard distillate.
Tasting Notes:
Nose: Toffee and toasted oak emerge out of the glass at first as the impression of the secondary cask works its magic. There are also hints of stone fruit, like peaches and apples, along with a touch of custard on the nose.
Palate: The palate features bold splashes of the stone fruits from the nosing notes, which are accented by toasted oak, butterscotch, and French vanilla. The mouthfeel is medium-bodied, which is ideal as it doesn’t distract from the light, sweet, tasting notes present in the liquid.
Finish: The finish is medium-length and leaves you with the gentle sweetness of toasted oak. A bit of marshmallow and earthy woodsiness persist through the end of every sip.
Bottom Line:
The secondary maturation and the bump in proof in this whiskey help it to stand up to your palate in the same way Shaboozey and Noah Cyrus hope to see their friend/partner stand up to the pains that haunt them. While blaming things on the stars skirts the accountability of those looking to numb their pain in a bottle, following the stars can also be a metaphor for holding your head high and looking upward. Starlight whiskey is a perfect match for such a metaphor.
9. “Vegas” with Smoke Wagon Uncut/Unfiltered Bourbon Whiskey
ABV: 57.09%
Average Price: $75
The Song:
We’ve got a two-for-one in this pairing, as Shaboozey mentions both “whiskey” and “smoke” while laying out his regrets about his Devil-may-care attitude toward his life of late. Following a “pretty lady” out of town and finding himself among the “low vibrations” and reminiscing on some of his hardships, he expresses the need for an escape from his escape. It’s an eminently relatable song about picking up the pieces when the risks you take don’t pan out quite as you planned them.
The Whiskey:
Smoke Wagon’s Uncut/Unfiltered expression is the bottle that put them on the map. Released in small batch blends, this particular bottle is batch 184A and features bourbon sourced from Indiana and aged between their distillery of origin and Las Vegas.
Tasting Notes:
Nose: Plum skin, cinnamon bark, and young oak hit the nose for a blend that really works well here. There’s also a certain dusty aspect to this whiskey that is as surprising as it is welcome. Further notes of green grape and sunscreen continue the surprises — both in that they’re atypical nosing notes and that they actually work well to elevate the sum of the parts.
Palate: Caramel, barrel char, and green grapes inform the palate, along with a healthy dose of black pepper. The flavor of charred red pepper comes across, as well as the robust mouthfeel finds every corner of the palate and seeps into your tongue.
Finish: The finish has chocolate pretzels and sage in spades, and it closes with barrel char for a medium-length finish that puts a lovely bow on the unusual assortment of flavors.
Bottom Line:
If you’re going to “live your life like it was one big Vegas,” then you’re going to need Sin City’s best bourbon by your side to drown out any doubts that arise. Luckily, Smoke Wagon’s Uncut/Unfiltered expression hits the spot whether you’re acting the part or simply nodding your head along to this song and living vicariously through Shaboozey.
10. “Drink Don’t Need No Mix” feat. BigXthaPlug with Mary Dowling Bourbon Whiskey Finished In Tequila Barrels
ABV: 46.5%
Average Price: $65
The Song:
The song with the most hip-hop vibes on the entire album features emerging rapper BigXthePlug. It sees the two exchanging verses about getting faded on an alcohol-infused adventure through downtown Nashville. BigX calls out their respective preferences, saying he “stays lit off tequila, Shaboozey wants whiskey, we tipsy and want every girl if she’s pretty.”
The Whiskey:
Aged for over 3 years and then finished in Reposado tequila barrels, this unique whiskey comes from Mary Dowling and is distilled by Rabbit Hole in Kentucky. The brand itself was created to honor one of the most interesting figures in the whiskey world, Mary Dowling, who is famous for moving her distilling operation south of the border during Prohibition. To honor that legacy, the brand decided to finish bourbon whiskey in barrels from Mexico’s most famous alcohol export.
Tasting Notes:
Nose: Lavender, roasted marshmallows, and toasted corn with butter and salt can be found on this particularly expressive nose. It also has a slightly youthful aspect, though that’s not a knock against it, as that plays well with the tequila barrel finish and allows some of the agave syrup to come through. Given some time in the glass, a bit of golden raisin and candied ginger also creeps into the nosing notes.
Palate: Star anise, toasted corn, and black tea come barreling across the palate with this whiskey. Black pepper soon blossoms and takes root at the roof of the mouth. It is notably drying at midpalate, causing you to salivate courtesy of the vegetal undertones and healthy helping of baking spice at midpalate. It also has an austere mouthfeel, coming across as clean and lean.
Finish: The finish is full of golden delicious apple skin and black pepper, and it’s pretty brief, which thins out the mouthfeel.
Bottom Line:
BigX is on tequila, Boozey is on whiskey, and neither of them needs a mix, so why not combine the best of both worlds in a single sip? Not only is this unique whiskey worth exploring on its own but there isn’t a single bottle of alcohol on shelves that pairs more perfectly with “Drink Don’t Need No Mix.”
11. “Steal Her From Me” with Larceny Barrel Proof Bourbon Batch B524
ABV: 62.7%
Average Price: $75
The Song:
Acknowledging the ephemeral nature of modern romance, Shaboozey weaves a tale in this song about another man’s lover falling for him and the inevitability of her soon falling for someone else. Crooning that “karma she’ll hunt you down, this town here is full of thieves…” it’s a song that espouses the age-old wisdom that “what comes around, goes around.”
The Whiskey:
Aged for 6-8 years, Heaven Hill’s Larceny Barrel Proof Bourbon is their premier wheated bourbon offering. With a backstory that honors John E. Fitzgerald, a treasury agent with a reputation for stealing some of his favorite barrels of whiskey out of bonded warehouses, this whiskey is the perfect match for this song. The B524 batch is new for spring 2024, with “B” representing the second batch of the year, “5” representing that it came out in the month of May, and “24” standing for the year it was released.
Tasting Notes:
Nose: Immediately nutty, with the aroma of fudge, brown sugar, and walnuts wafting out of the glass, this is a nose that reminds you of Snickers ice cream bars. That’s as opposed to the candy bar because there’s also a bit of oak and vanilla ice cream hanging in the air along with a streak of oak.
Palate: The palate sees the oak influence ratcheted up as dark chocolate and nougat notes rest on a bed of peanuts. The ABV can certainly be felt as a heavy punch of alcohol hits at midpalate and persists through the finish of this flavorful and well-refined whiskey.
Finish: The finish of this chewy whiskey is marked by black pepper and candied peanuts, along with a surprising bit of lavender and lemon zest, which helps to brighten each sip and add a bit of nuance.
Bottom Line:
Larceny Barrel Proof Batch B524 fits the bill for “Steal Her From Me” thanks to the fact they both share an overarching theme of thievery, but it really helps that the high ABV will dull the blow of having your partner stolen. Thankfully, an elevated proof point won’t be the only thing keeping you company, as the sweet Snickers tasting notes in this bourbon will also sweeten the deal and help you forget about the (stolen) love that you lost.
12. “Finally Over” with Wild Turkey 101
ABV: 50.5%
Average Price: $29
The Song:
On the closing track of Where I’ve Been Isn’t Where I’m Going Shaboozey wrestles with the pressures of his newfound fame, fearful of returning to obscurity and “staring down the whiskey” wondering whether he’ll have to sell his soul to maintain the popularity he fought so hard to achieve. Ultimately, he’s made peace not only with the journey that led him here but also with whatever fate may await him, ending the album with the line, “I’m glad it’s finally over.” For Shaboozey, this is certainly the end of the beginning.
The Whiskey:
Wild Turkey 101 is the brand’s flagship expression, and it is ubiquitous on back bars across the country. The bottle’s new packaging was released in early 2021, but Master Distiller Jimmy Russell prides himself on this expression above all others because its flavor profile has remained consistent for decades.
Tasting Notes:
Nose: Caramel, almond extract, and orange rind are featured heavily on the nose of this whiskey. Given some time to rest, you’ll also pick up notes of buttercream with an orange zest, nutmeg, and a bit of dried cranberries.
Palate: On the palate, that interplay of citrus zest, baking spice, and dried cranberries comes fully into view. A bit of cinnamon and caramel add elements of sweetness to each sip, and though the mouthfeel is fairly lean, it features a nice punchiness at 101 proof that keeps you cognizant of the fact that this is fine bourbon whiskey.
Finish: The finish is where the sizzle of alcohol ratchets up a notch, giving an indication of how Wild Turkey 101 got its reputation as a raucous pour for rowdy imbibers. That said, the finish isn’t remarkable, but as it ends off with caramel and baking spice, it encourages you to line up another pour and go in for a second glass.
Bottom Line:
Wild Turkey 101 is perhaps the quintessential American whiskey. Pouring bourbon in your glass comes with a set of expectations that Wild Turkey 101 is perfectly suited to live up to — caramel, oak, baking spice — sure, but also a proofy bite and a solid finish that warms your chest and fills you up with liquid courage. As you listen to Shaboozey, reckon with his journey toward stardom and contemplate the choices that led you to your current position in life — acceptance is key, and courage is probably necessary. That’s why Wild Turkey 101 is the perfect whiskey to pour while you take stock of the fact that where you’ve been isn’t where you’re going.