Good music and a good drink often go hand in hand, but do we ever really stop to appreciate the pairing?
We do now, because 2025 has been a banner year for rap music, but it’s also quietly been an incredible year for new whiskey releases, even in the face of cooling sales. The real secret is that whiskey has not only become better than ever in terms of quality, but it’s also being appreciated with greater intention. The ritual of spinning your favorite vinyl or hearing new music at an event is always enhanced with something high-quality in your glass, but the key is to choose your libations like you choose your tunes — play nothing but the hits.
Since this is our first spin on blending new music with new whiskey, I’ll draw inspiration from some of the best rap songs of 2025 and pair them with some of the best bottles in the same span. The stories behind these songs and spirits are aligned in one way or another, but the real key is that the mood set by each song syncs perfectly with the vibes evoked by every flavor in your drink.
They say music is how we decorate time, and with these whiskeys on deck, you’ll want to savor every moment.
Enjoy some sound sipping with ten of the best rap songs and whiskeys to enjoy together right now.
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The Song: Rapsody & Madlib “Daddy’s Girl”
The Drink: Four Roses Limited Edition Small Batch Bourbon 2025
ABV: 54.55%
Average Price: $250
The Pairing: “I still ain’t got my roses, I’m waiting, I bought vases!” It’s true that Rapsody too frequently gets overlooked as one of the best lyricists alive today, but her twin collaborations with Madlib mark a perfect time to give the North Carolina rhymer her flowers. Of the two, it’s “Daddy’s Girl” with its lush soundscape that lends itself to laid-back listening enjoyment over a glass of whiskey.
That brings us to the 2025 expression of Four Roses Limited Edition Small Batch Bourbon. The highly sought-after bourbon in 2025’s release already has a spot reserved on our annual best-of-the-year list, blending rich, sweet notes with plenty of punch to remind you that this is, after all, an adult beverage. Where the delicious, faintly peppery finish on the Four Roses lingers long after each sip, you’ll want to play “Daddy’s Girl” again and again, as it’s a potent track that always seems to end all too soon.
Better make that drink a double.
The Song: Your Old Droog & Madlib feat. Wiz Khalifa & Jay Electronica “Woodstock 2029”
The Drink: Michter’s Bomberger’s Declaration PFG (Precision Fine Grain)
ABV: 50.1%
Average Price: $380
The Pairing: In one of the more unexpected, yet incredible, collaborations of the year, the team of Your Old Droog and Madlib is joined by Jay Electronica and Wiz Khalifa for a mesmerizing track that sees each of the rappers at his respective best. While Jay Elect kicks things off with a prototypically pensive 16, YOD follows with a sharply penned verse that instantly made me wonder aloud whose contribution was better. Not to be outdone, Wiz follows suit with a performance that his hardcore fans will applaud, as he extols his commitment to three of his greatest loves: counting cash, working out, and rolling up.
The perfect drink to go with this song is a nice pour of Michter’s Bomberger’s Declaration PFG. While Bomberger’s has been an ongoing release from the brand for a few years now, this PFG edition is a totally new and unexpected riff on the modern classic. The whiskey is first fully matured in an American oak barrel and then transferred to a second new French fine grain oak barrel, which undergoes proprietary toasting and a uniquely specified char level to fine-tune the flavor. The French oak in that second barrel comes from a variety of old-growth forests, including the Tronçais, Allier, Nevers, and Vosges. Simply put, the trees harvested for those barrels are typically at least 200 years old before being used to store and mature the whiskey in your glass.
It’s that blend of trees and rich history that accompanies them that gives you a lot to savor (and think about) while sipping Bomberger’s PFG. It’s a complex dark horse for whiskey of the year that perfectly complements the unexpected greatness of this track.
The Song: Bruiser Wolf, Benny The Butcher & Harry Fraud “Raised By Dope”
The Drink: Heaven Hill 19-Year Wheat Whiskey
ABV: 50%
Average Price: $300
The Pairing: Bruiser Wolf’s hypnotic stop-and-start cadence flows a bit more swiftly on his new single with Benny The Butcher and Harry Fraud, perfectly keeping pace with Fraud’s luxurious beat. By the time Big Butch steps to the plate, the song is already great, but his unique brand of bragodocious, been-there-done-there bars takes things to the next level. Benny always raps with a self-assured air of confidence, and he sounds perfectly at home on this one. These repeat collaborators are really hitting their stride.
When it comes to Heaven Hill, they hit their stride sometime in the early 2000s after recovering from a catastrophic fire, and they haven’t looked back ever since. Case in point, this mind-blowing 19-year-old wheat whiskey. It’s pretty atypical to see wheat whiskey on the market these days, but even more so when you consider the ample age on this one. Heaven Hill’s experience is on full display with this incredibly mature wheat whiskey, producing one of the year’s best releases seemingly out of thin air.
Bruiser and Benny have given us a banger already this year, but this song really lends a lot of weight to their track record in the same way Heaven Hill’s illustrious reputation is only bolstered by unexpected expressions like this one. It’s only right that you enjoy them together.
The Song: The Cool Kids, A-Trak & Sango “95-South“
The Bourbon: Wild Turkey 8-Year 101 Bourbon
ABV: 50.5%
Average Price: $45
The Pairing: When Chuck Inglish exclaimed, “Bring another bottle, that’s that potion!” over this up-tempo beat, seemingly ripped out of Miami in 1991 and Miami in 2091 at the same time, I knew precisely which whiskey to pair it with: Wild Turkey 8-Year 101 Bourbon. It’s a song that marks The Cool Kids’ triumphant return to their classic sound in the same way that Wild Turkey 8-Year 101 is a return to the specs of the bourbon the brand was producing in the early ’90s.
That said, neither this song nor the bourbon paired with it is trapped in the past. The whiskey is a real party starter and a glimpse into the future of Wild Turkey, which anticipates making this an ongoing age-stated offering that bourbon enthusiasts can grab year after year. Similarly, The Cool Kids’ newest single blows the doors off what we’ve seen so far from the rap game in 2025, providing a fresh twist on their typical nostalgia-twinged formula that’s poised to make Mikey and Chuck two of rap’s biggest fourth-quarter winners.
Not content with drawing inspiration from the classic bass beats and bourbon of the past, or offering a glimpse into the future, both this standout single and this whiskey serve as reminders that living in the moment is the best gateway to timeless enjoyment.
The Song: Ghostface Killah “Rap Kingpin“
The Drink: Very Olde St. Nick 20-Year Bourbon
ABV: 59.1%
Average Price: $1,400
The Pairing: The beauty of Ghostface Killah’s new “Supreme Clientele 2” album is that you can tell how carefully it was constructed. It takes time to create a work of art so steeped with nostalgia in today’s age that maintains all of the authenticity that made the original album such an unassailable classic. On “Rap Kingpin”, Ghost flips two of the most legendary beats in hip-hop history, combining them with his usual vivid lyrical display where he nods to his length in the game, rapping that he’s holding “Old money, old 20s” while admiring a statue of himself in the projects. It isn’t vanity, it’s self-appreciation. After over 30 years in the rap game, there’s still no one who can do what Pretty Tony does.
Channeling the past is likewise one of Preservation Distillery’s more impressive feats, as they semi-regularly break out hyper-aged bourbons from a bygone era that show how prescient and selective its founder, Marci Palatella, was and is. American whiskey at the 20-year mark is incredibly rare, in part because it has a tendency to deteriorate in quality, and also because so few brands and distilleries had the forethought to carefully age bourbon for so long. With this particular release, not only is the liquid’s quality indicative of forward thinking, but it’s a flex in itself, as one of the best bourbons to be released in the last 5 years.
It’s been 25 years since Ghostface released the original Supreme Clientele, and for the lion’s share of that span, this whiskey was getting better with time. Suppose you want to pause and appreciate, not just Ghostface’s latest single but also his legendary career. In that case, you’d do well to enjoy it alongside a mature bourbon like this— one with remarkable flavor that tastefully brings the past into the present.
The Song: billy woods “Cold Sweat”
The Drink: Knob Creek 21-Year Bourbon
ABV: 50%
Average Price: $250
The Pairing: This song from underground virtuoso billy woods’ fantastic “Golliwog” album isn’t all that new, but it sounds that way every time I hear it. Buried 2/3rds of the way through the dense, dark album like a black truffle, this song finds woods recounting some of his most harrowing nightmares (enduring Math Hoffa’s homophobia and living on W 86th St. with two kids by his ex, among them) before the song takes a fully comedic twist and takes the perspective of his landlord.
The link here is that as bourbon matures past a certain point, producers almost invariably expect the liquid to deteriorate significantly. Defying those expectations, Knob Creek 21 is one of the rare bourbons-of-a-certain-age that actually appear to have improved over the 20-year mark. While there are many hallmark flavors you expect from hyper-aged bourbon, there’s a lively texture and a bevy of sugary flavor notes that demonstrate this whiskey has literally and figuratively hit the sweet spot.
Just as woods’ song gets better and better (for the protagonist), the longer it goes on, Knob Creek 21-Year Bourbon takes a similar track. Stick it out with both of them until the end.
The Song: Mobb Deep “Against The World”
The Drink: Old Cassidy Small Batch Bourbon
The Pairing: When the late/great Prodigy opens this song with “Stronger than ever…I’m back!” it sent a chill down my spine, and sent my thoughts instantly racing to Rare Character’s brand-new Old Cassidy Small Batch Bourbon. Rare Character’s founder, Pablo Moix, confirmed that there’s a significant percentage of well-aged whiskey in this blend, which builds on the impeccable reputation of Old Cassidy’s inaugural single-barrel release, selected by yours truly in late 2023.
That’s not unlike the way “Against The World”, the intro to Mobb Deep’s new album Infinite, perfectly sets the tone for the record by recapturing the legendary group’s gritty mid-’90s energy while taking it in a new direction with both rappers’ more seasoned and polished vocal texture. The added dimension of this being the group’s first album to feature a posthumous member makes the song even more haunting yet alluring, as Havoc shows he can remain in lockstep with his fallen partner in rhyme all these years later.
It’s hard not to be mesmerized by the mere prospect of Mobb Deep and Old Cassidy returning in 2025, but the fact that they both deliver on that promise in such a significant way is a credit to the masters who worked on both, making it an ideal pairing.
The Song: Stove God Cooks “Marvin Ye“
The Drink: Kings County Barrel Proof Empire Rye
The Pairing: Stove God Cooks’ viral song Marvin Ye only at first seems like the crescendo of a slowly building hype train, but with rumors of a big-budget album looming, it’s more likely this is just the start of another hot streak. It’s that specious trajectory that calls to mind New York’s Kings County Distillery, which just released one of its best whiskeys yet after 15 years in operation.
While it’s true that this song was released late last year, predating his current streak, the fact that it gained traction this year only adds gravity to his impressive momentum. Similarly, Kings County has previously released barrel proof Empire Rye single-barrels, but this nationwide release marks the first time a lot of people have access to it. Those folks are learning what New York already knew: Kings County can rival any brand in the country.
While 2025 feels like Stove God Cooks’ arrival on rap’s big stage, all signs point to things getting even greater later.
Jay Worthy feat. Boldy James “Choosing Shoes”
The Drink: President’s Choice Rye
ABV: 58.55%
Average Price: $225
The Pairing: The production on the lead single of Jay Worthy’s stellar “Once Upon A Time” is smooth as butter and perfectly built to show off his velvet glove approach to rapping. Spinning a web silkier than a spider, it’s no surprise to find his verse has you hanging on his every word by the end. When Boldy finally saunters over the beat with his signature reserved precision, he spells out one of the keys to his success, “I ain’t have to catch up with my crowd, my crowd caught up with me.”
It’s that commitment to staying the course that has afforded Old Forester a loyal fanbase throughout whiskey’s rising popularity, and sees them marching to the beat of its own drum with this intriguing new rye. While many other brands were chasing the so-called rye resurgence, Old Forester took its time and delivered a show-stopper when fans least expected it.
Jay Worthy has spent more than a decade defying disbelievers, and though he’s put together an impressive career already, you can’t help but feel he’s charting new territory on his latest album. Moving at your own pace ensures you’re always in the right place at the right time. It’s a secret you’d be wise to appreciate while sipping a glass of President’s Choice Rye Whiskey.
The Song: Clipse, John Legend, and Voices of Fire “The Birds Don’t Sing”
The Bourbon: Wild Turkey Master’s Keep Beacon
ABV: 59%
Average Price: $500
The Pairing: The most heartfelt song of the year is a thoughtful celebration of life, and a fitting tribute to the late parents of 2025’s most celebrated rap group, Clipse. A similar celebration finds two generations of the Russell family joining forces to create Master’s Keep Beacon, which marks the final chapter in the limited edition lineup that Master Distiller Eddie Russell began and now welcomes his son, Bruce, into the fold.
Though “The Birds Don’t Sing”, the intro to Clipse’s tour de force rap album of the year frontrunner Let God Sort ‘Em Out, has been out for a while, the recent release of its music video on the heels of an electric performance at the Vatican have given the track new life, which is why it warrants an inclusion here. Intros are typically a distant memory by the time an album reaches its conclusion, but this particular song undergirds the entire album, serving as its beating heart, and will likely persevere as one of the group’s greatest songs ever.
For its part, Master’s Keep Beacon is already considered one of the best whiskeys in the critically acclaimed series, featuring 10-year-old bourbon distilled by Bruce Russell, which is then blended with 16-year-old bourbon distilled by his father, Eddie. The results are a multi-generational masterpiece that serves as a fitting closing chapter to the premium lineup.
This is luxury whiskey, and Clipse represents luxury rap better than anyone on the planet. Still, the layers of family history that produced these works of art are the lifeblood of their substance, making them ideal for enjoying together.
I’d highly encourage you to enjoy them together with a loved one.