23 Bourbons You'll Regret Buying

Like a moth to the flame, human beings are naturally drawn to loving shiny objects. It must be encoded somewhere in our DNA — who doesn't like owning attractive and expensive items? That being said, looks and price tags can be deceiving, and making choices based on these elements can easily get you into trouble. When it comes to bourbon, it's no different. Human beings like to think that an inflated price and a striking bottle means it must be good, right? Not necessarily, because a humdrum bottle or a bourbon at a low price point isn't always going to taste like nail polish remover. 

Bourbon aficionados will tell you that when purchasing a worthwhile whiskey, you should never be swayed by appearance and you should always do your research. It's called common sense. But they'll also (begrudgingly) be the first to admit that they still end up learning through experience. That's why we're sharing the following selection of regrettable bourbons, to save you from falling victim to shiny object syndrome — because no one likes buyer's remorse. One note: All the prices listed were accurate as of April 2022, but the price may be different in your area.

In 2012, Jefferson's Bourbon teamed up with OCEARCH (an internationally recognized nonprofit that tracks and studies keystone marine creatures) to test out a new bourbon-related theory. If you have access to bourbon and a water-born research vessel, then why not? The theory was that the constant movement of bourbon sloshing around in wood barrels would in turn make the whiskey age faster. 

That's how Jefferson's Ocean Aged at Sea was born. The test barrels remained on OCEARCH's vessel for three years, even passing through the Panama Canal numerous times according to the bourbon company. When Jefferson's master blender tapped the casks, the sugars in the bourbon had caramelized and turned into a viscous, black liquid. (That's a good thing.)  

However, SLB Basement Bourbon Bar (via YouTube) laments paying $80 for a bottle, claiming that it was a stupid waste of money to spend on a bottle with a good story. Every other aspect — nose, palate, and finish — was horrible because the bourbon had an "overwhelming taste of leather and tobacco and a lot of bitterness." Meanwhile, Thirty One Whiskey explains that Jefferson doesn't distill anything — the company just receives bourbon from other sources, then labels and sells it. Sounds like most of the finances for this experimental spirit were put to really good use in the marketing and branding department. Maybe this one should be tossed overboard.

Garrison Brothers is the first legal whiskey distillery outside of Kentucky, meaning they've obtained the proper permits from the Texas Alcoholic Beverage Commission (TABC) to lawfully produce and distribute spirits through different businesses, vendors, and retailers (via Cobb & Counsel).

Remember that old adage, "First the worst, second the best?" Perhaps being the first at something isn't always a good thing. Reddit users say point-blank that Garrison Brothers is stupidly overpriced. In response to a question about some serious shade being thrown at the company, bourbon fanatics on Reddit chimed in with their two cents. They claimed that the bourbon is poor quality for the price you pay and that it "doesn't even come close to holding its own against cheaper competition." But maybe consumers' expectations are simply too high? Paste Magazine reports that dissatisfaction with pricing is a universal consumer woe regardless of the bourbon.

Ultimately, the whiskeys produced at this distillery tend to taste incredibly young or like "chewing on a yew branch" (via YouTube). While a bottle won't make you break the bank (they start at $40 to $50), the woody, funky taste seems to be a running flavor in this distillery's production line. And if the Reddit comment "it tastes like rotting peanuts and cardboard" doesn't make you a little hesitant, then by all means, go forth and experiment.

Located in Louisville, Kentucky, Angel's Envy takes pride in creating small-batch spirits that are finished in one of four different casks: port, rum, sherry, and tawny. You can purchase a bottle for as little as $40 (or upwards of $4,000). The company has been distilling for 200 years, so it has really racked up quite an impressive reputation, with its Cask Strength release in 2013 dubbed Best Spirit in the World.

The Whiskey Jug reviewed Angel's Envy Kentucky Straight Bourbon, and the tasting notes seem to be echoed across the web. Basically, this bourbon is cloyingly sweet since it's finished in port wine barrels. The distillery's website describes aromas of subtle vanilla, raisins, maple syrup, and toasted nuts. So, that sounds like ... granola? Meanwhile, SLB Drinks says that the flavor profile "tastes like someone mixed bourbon and maple syrup and then added some artificial sweetener for the hell of it." Redditors echoed this sentiment, saying that it tastes artificially sweet and bitter, and is more "like watered down bourbon mixed with watered down wine." 

So if you like port wine (or granola) and have a spare $40 to $50, then perhaps this is your new nightcap.

If someone came to you and described a bourbon as horrid brown water, as per a Reddit review, would you want to try it? Hopefully not, though it's understandable that your curiosity might be piqued. What if you were told that the inspiration for this bourbon comes from a famous racing horse? Well, according to Lexington Bourbon's website, that's the case. It also explains why the label has a picture of a brown horse on the front.

Produced by Western Spirits Beverage Company, a bottle of Lexington Bourbon will run you around $42, as sold on Caskers. This whiskey was also rated 95 points in 2012 by The Tasting Panel and won a silver medal at the San Francisco World Spirits Competition in 2016. But just because something has won medals doesn't mean it's universally adored and beloved. 

Reviews on Flaviar say it's "Too rough and not very enjoyable," and Distiller comments won't give you much more confidence: "Flat, thin and weak. Literally tastes like dirt." Meanwhile, customers vent their frustration for succumbing to shiny object syndrome — the bottle looked cool. For the price, Kentucky Bourbon seems to fall flat, and tasters would probably agree with the Reddit user who wrote "I am pretty sure whatever is in this bottle came out of that horse." 

Kentucky Gentlemen is brought to you by the Sazerac Company (known for Fireball, Myer's Rum, and Southern Comfort, to name a few), and distilled by the seventh-largest distillery in the world, Barton/1792 Distillery (via Whiskey University). It's easily one of the first whiskeys to be thrown into the pit of most regrettable bourbon purchases. 

Tasters on Distiller claim that this bourbon is flavorless, hard to get down, and incredibly bland and boring. They also say it tastes rough and is cheap for a reason (it goes for around ten dollars for a 750-milliliter bottle). The verdict is that should you choose to drink this spirit, you're going to want to use it as a mixer. And you're also going to want a nice, greasy meal the next morning to help you with that hangover.

Whiskey Warehouse reviewed this spirit on YouTube, pointing out that it's thin and really has nothing going for it, other than smelling (and tasting) like watered-down bourbon. One Reddit user sums it up nicely by saying "There's nothing 'gentlemanly' about it." "It's fun to throw into blind tastings," another user adds. Well, at least the price tag under $20 makes it a good gag gift.

Blade and Bow's conception starts with the legendary Stitzel-Weller Distillery in Louisville, Kentucky, whose claim to fame is being founded by the man behind Pappy Van Winkle (via Whiskey ID). The distillery closed in 1992 but was resurrected in 2014 by Diageo, a company based out of London that specializes in a broad range of spirits.

Blade and Bow is a 91 proof, $50 blended bourbon that has no age statement on the bottle. All that's known about this whiskey is that the liquid parties involved are aged for a minimum of four years, and that a proportion of the Stitzel-Weller bourbon distilled prior to 1992 is also mixed in. According to reviews on Distiller, this bourbon tastes cheap and burns going down. SLB Basement Bourbon Bar goes into detail about this regrettable purchase, saying that it is very grainy, bitter, thin, and young, and the alcohol burn isn't anything to joke about. 

On each bottle of Blade and Bow is a collector's key, and if you collect all five keys, you'll become a member of the executive club. As a reward, your name is engraved on a golden mint julep cup stored at the distillery, according to Reddit users who have joined the club. Maybe it's a sign that this bourbon needs to be locked away.

What tastes like creamed corn blended with scorched plastic, but comes in a really cool genie bottle? Apparently, to one Redditor, it's Willet Pot Still. The Willet family lineage and distilling experience extend back multiple centuries, but it was only in 1936 that the Willet Distillery was established on the family's property, three years after the end of prohibition. 

Willet Pot Still is considered a Kentucky straight bourbon, meaning it has been aged a minimum of two years in brand new charred oak barrels, per New Riff Distilling. In total, this whiskey has been aged between eight and 10 years and has actually won a Double Gold Medal ... for the bottle design, which is supposed to resemble the historic pot still that the distillery used for generations (via Caskers).

According to the distillery's tasting notes, this 94 proof bourbon smells of "vanilla lemon cake" and tastes like caramel, vanilla, citrus, and spices. Meanwhile, Caskers describes butterscotch, molasses, brown sugar, and coffee. However, taste is subjective and Reddit reviews compare the flavor to "bitter rubber," while a consumer on Distiller reports "hints of Redman chew spit and unsweet tea fermented in a styrofoam cup in mid July." 

Unfortunately, you can't make a wish and ask for your $50 back. After all, this bourbon isn't really a magic bottle.

If super flavorful, bold, and bright bourbon is your calling, then you'll probably want to steer clear of Basil Hayden's Kentucky Straight Bourbon. The bottle is spectacular, with an intricately etched label that compliments the amber hue of the bourbon itself. But unfortunately, this spirit doesn't seem to live up to its trademark slogan: "You never forget your first sip of Basil Hayden." Or maybe it does, but not in a good way.

This 80 proof, light-bodied bourbon is produced by Beam Suntory, the daughter company of Jim Beam and Suntory Holdings (and third-largest producer of distilled beverages worldwide in 2020, per Statista). Across the web, bourbon reviewers use almost identical adjectives to describe Basil Hayden's Kentucky Straight Bourbon. On Youtube, someone commented that "It's like bourbon for people who don't like bourbon." Meanwhile, Reddit users stated that it was bland, tasted like flavored water, and wasn't worth the price. 

When you hear comments like that, it makes you wonder if this is the same bourbon that won a Silver Medal at the 2020 International Spirits Challenge and a Double Gold at the 2020 San Francisco World Spirits Championships (via Liquor.com).

KOVAL Distillery doesn't believe in limiting itself to crafting just one single artisanal spirit, as evidenced by its varied selection of spirits including bourbon, gin, and flavored liqueur. Every step is carefully monitored, from sourcing herbs, grains, and spices from vetted farmers to using state-of-the-art technology to keep its products consistent.

Maybe the calculated and scientific vibe is what some bourbon tasters are picking up on, because as one Redditor put it, "KOVAL tastes like it was made in a lab by scientists that had never tasted whiskey themselves and the flavor was described to them by a guy that loves terrible whiskey." The artificial and chemical taste was also a source of disgust on Distiller, with samplers commenting that it was heavy on the ethanol. It goes without saying when a bourbon provokes a description like "vomit inducing turpentine," you should probably think twice before investing $50 for a bottle.

Though KOVAL has received over 100 international awards, perhaps it should focus its energy on perfecting one spirit instead of tackling multiple products all at once.

Produced and distilled at Beam Distillery, Old Crow Straight Bourbon Whiskey is the least expensive option on this list, available at around $10 for a 1.75-liter bottle with a discount (via BevMo.com). More typically, it goes for $22 to $25 which makes you wonder about the aphorism "You get what you pay for."

This 80 proof has a nice, golden color and a label that looks like an old vintage medicine bottle. This makes perfect sense because the bourbon is named after Dr. James Crow, a Scottish physician and chemist who invented the sour mash process, an important step in distillation (via Whiskey Raw). On YouTube, the folks from It's Bourbon Night describe it as having a sweet, fruit nose but a stale, nutty, incredibly watered down taste, while Modern Thirst says it's bottom shelf, young tasting, and best used for mixing. Redditors are more direct: "Old Crow will make you want to quit bourbon."

Perhaps the quality has diminished over time because Beam Distillery claims that this exact whiskey has graced the desks of US presidents, as well as acclaimed writers like Mark Twain. If these famous individuals had more options, would they have still picked Old Crow?

Established in 1935, Heaven Hill Distillery is the creator of Larceny Barrel Proof Bourbon, a small batch, wheated bourbon that comes out three times a year. With Larceny's slogan "So smooth, it's criminal," you might unintentionally reach for your wallet, you know, just to make sure it's still there. This bourbon is aged six to eight years and has won multiple awards, including Whiskey of the Year by Whiskey Advocate in 2020 (via Kentucky Bourbon Trail). 

Per the distiller's tasting notes, Larceny has aromas of toasted bread, maple, and cinnamon, and a reported taste of molasses, fig, and hazelnut. You would think this spirit would be big, bold, and, live up to the hype. But Distiller reviewers point out that it has an intense heat, too much cinnamon, and is akin to lighter fluid. One Redditor even claimed that they "poured it down the sink after a dram and felt bad for the drain — and my wallet."

According to Merriam-Webster's Dictionary, larceny is defined as "the unlawful taking of personal property with intent to deprive the rightful owner of it permanently." Sounds like some consumers fell hook, line, and sinker for a good story and mastermind publicity, ultimately ending up $50 short. That's so smooth, it's criminal.

This 92 proof straight bourbon whiskey hails from Tuthilltown Spirits Distillery, located in a little town in Hudson Valley, New York. Bright Lights, Big Bourbon is the second whiskey this distillery has produced, the first being Hudson Baby Bourbon, which has been since been discontinued, per Distiller. According to The Manual, it turns out the two whiskeys are one and the same. Sneaky. 

Baby Bourbon (version 1.0) was groundbreaking in that it was the first legal whiskey made in New York since prohibition (via DrinkUpNY). Perhaps not being able to previously practice the fine art of distilling is what the tasters pick up. How else can you justify Redditors when they say that "It's bad enough to make you want to curl up into the fetal position and sob like an infant."

The distillery's website states that this bourbon is aged a minimum of three years and has a mash bill consisting of 95% corn (100% from New York) and 5% malted barley. The site also says that Bright Lights, Big City smells of vanilla and oak, with a flavor of stone fruit, corn bread, caramel, and cashews that "lingers long after your final sip." Reviews such as the one by Bourbon Culture sound off with regard to the ethanol smell and creamed corn taste, but according to Reddit users, falling for good marketing and paying upwards of $50 is what really grinds their grain.

Knob Creek's Kentucky Straight Smoked Maple seems to be, according to some bourbon fans, a bad execution of a good idea. One Redditor said, "It's seriously the only bottle I've poured down a drain." To be fair, not everyone wasted their whole bottle; another commenter on the same thread said that this whiskey is a great ingredient in baked beans.

This bourbon is so sweet that it's been likened to a bottle of diabetes, and one reviewer on Flaviar said that the sweetness was bad enough to hurt their teeth. Another chimed in that it was like drinking straight maple syrup. Taking a shot of Knob Creek's Smoked Maple sounds like one of those questionable challenges that dare you to record yourself doing something ill-advised like eating a spoonful of cinnamon or, you know, drinking a jug of maple syrup. When it comes to this bourbon, save yourself a trip to the dentist. You really don't need any cavities.

Those who aren't knowledgeable about bourbon might be led to believe that a whiskey thief is someone who breaks into a rackhouse and escapes into the night with a full barrel of juice. As intriguing as that sounds, a whiskey thief is just a simple tool that allows master distillers to sample some of the aging liquid for quality control purposes, according to Distillery Trail. Whiskey Thief Uncut Unfiltered may sound like it's coming to a theater near you, but it's actually a bourbon brought to you by Three Boys Farm Distillery.

This whiskey is aged for four and a half years in new American charred oak barrels. Whiskey Thief Uncut Unfiltered is described by the brand as having caramel and honey notes, a woody edge, and a hint of white pepper. Maybe an olfactory thief has somehow stolen tasters' sense of smell, because all they seem to be getting is vanilla, and a lot of it, too (via Distiller). Perhaps this overwhelming scent would be permissible if it was marketed as such, but other reviews state that it's sadly just an average bottle of booze that's also extremely harsh and bitter. Like a stranger in the night, it's best to just stay away from this one.

Have you ever heard of the Kentucky Chew? That's what the folks at Jim Beam call it when you take a big gulp of bourbon and move it around your mouth to get all the flavor nuances (via The Bourbon Room). Now, hold onto that concept for one second. Imagine the taste of Kentucky bourbon whiskey with the essence and spice of fermented peppers, garlic, and vinegar. Imagine Kentucky Chewing on that. It's cringe-worthy no matter how you look at it. 

George Dickel is actually the flagship spirit from Cascade Hollow Distillery. Someone thought it was a good idea to hook up with Tabasco brand hot sauce and bottle and sell the offspring for around $25. Quite frankly, Cascade Hollow Distillery jumped the shark on this one. What's even more mind-boggling is that in 2018, this bourbon won Gold at the San Francisco World Spirits Competition. Maybe the judges had incredibly tired palates by the time this disaster came up for judging. 

Distillery Trail writes that the Tennessee whiskey rests for 30 days in barrels that previously held Tabasco hot sauce. If you can stomach it, the juice is best in a pickleback. While one Redditor said it worked well in a Bloody Mary or an oyster shooter, the consensus was that it was nasty on its own. As one commenter on The Whiskey Jug says, it "tastes like someone spilled vinegar in sweet whiskey." Hard pass.  

In case you were wondering, yes: This is actually named after someone's grandfather. Back in 1882, third-generation distiller Raymond B. Hayden wanted to immortalize his grandpa by creating a memorable bourbon, according to Vinepair. These days, it's part of the Jim Beam empire. The man whose face has been immortalized on these bottles is none other than first-generation distiller Basil Hayden Sr., whose namesake bourbon also appears on this list.

Old Grand-Dad is actually quite memorable, but not in the way little Raymond was hoping. While Basil Hayden's tasted watered down and not worth the money, Old Grand-Dad pivots 180 degrees into the land of long-lasting acetone burn devoid of taste (via Distiller). At least it's only around $15, so you're not killing your wallet. Per Saucey, back in the 1920s, physicians could legally prescribe it for conditions like high blood pressure and pneumonia, and this bourbon tastes about as good as medicine. Old Grand-Dad doesn't do much for modern-day tasters, since it's only palatable as a mixer — or preferably, not at all. As one individual writes at Distiller, "it's probably a bourbon your old grand-dad would be content with, but I would suggest you and him trying other things." Ouch, (alcohol) burn.

In bourbon's infancy (you know, its "Early Times"), it seemed to be completely permissible for whiskeys to be a little rough around the edges. Per American Whiskey Trail, early American whiskey was mostly made by amateurs and sold while it was still young and fiery, so it probably didn't taste all that great.

Maybe the folks at Early Times took the whole historical angle a wee bit too far. One taster compared this bottle to "grass clippings and gasoline aged in turpentine barrels," which doesn't sound like anything we'd want to put in our mouths (via Distiller). Others point out that it's bitter, astringent, and reminiscent of cherry NyQuil. When someone says that the "cherry flavor is way too loud. Like the 'crying baby on an overnight airplane flight" kind of way-too-loud,' it's time to reevaluate. At least Early Times is giving bourbon lovers some bang for their buck: For the low price of around $22, you can buy one liter of this sweet Nyquil-esque bourbon.

First thing's first: this isn't Kentucky bourbon. It's from the land of frigid cold and really big lakes (Minnesota). While bourbon can technically come from anywhere in the US, maybe Minnesota should leave it to the experts down in Kentucky.

Bourbon drinkers unanimously agree that Paddleford Creek is pretty vanilla. As in, there's not much going on, and it's overwhelmingly reminiscent of potpourri — lots of wood and lots of bad vanilla. "There's some vanilla and brown sugar in the beginning, but it's immediately replaced by an overwhelming flavor of oak. It's not the pleasant aspects either, it's more like licking an oak plank," wrote Thirty One Whiskey. Don't expect to impress your friends by pouring from a bottle of Paddleford Creek (even though the label is pretty darn cool ... which is all it seems to have going for it), because, as one observer on Distiller states, it "just doesn't do much of anything." Unfortunately, Thirty One Whiskey agrees, stating that it's "fairly mediocre." Ouch. Sounds like this bourbon is stuck up a creek without a paddle.

Naming your bourbon "Two Stars" doesn't seem like that great of a move. Nobody wants to go see a two-star movie. Spoiler alert: The name ended up being a self-fulfilling prophecy. The idea is there, but it just didn't follow through. It's like a story without any real plotline — it may be entertaining, but you're bound to get confused and left wondering what just happened.

Thirty One Whiskey writes that the name is supposed to represent the two stars on the Louisville city flag. Paying homage to Kentucky is a good start. Sadly, it's also rated two stars by many reviewers on Distiller (as one taster laments, it was $20 down the drain).

Why the sub-par reviews? Its flavor is described as vanilla and something medicinal ... and mint. Redditors don't recommend it. Another Distiller commenter even noted that it reminded them of a breath mint or menthol cigarettes, sans tobacco. There's also a sizeable ethanol burn, which ended up leaving some bourbon aficionados in gastric distress. It sounds comparable to taking a mouthful of whiskey mixed with Listerine (At least you'll kill all the germs, right?).

Winchester Straight Bourbon is the product of individuals who are probably more interested in the money side of the distilling world than the crafting process and end product. Why such harsh words? Simply because the goal of this distillery — TerrePURE Spirits, alias Terreesentia — is to reduce the aging time a whiskey needs from years to hours (via Thirty One Whiskey). Whiskey Advocate writes that this is called the TerraPURE process, and it utilizes ultrasonic waves to speed up the aging process from years to a mere day (and a week or so to rest).

That doesn't sound like it can go bad, does it?

Here's the thing. Britannica writes that the art of distilling has been around since 800 BCE. It's most definitely a science and craft that takes extensive knowledge, time, practice, and patience to master. While experimenting is cool and all, it's not cool to try and act like the bourbon that has been aging for 24 hours is going to taste just as good as the whiskey that's been aging for five or more years. As Thirty One Whiskey writes, "Aging happens for a reason — namely to give the spirit some depth and complexity that otherwise is missing. This is something that other rye whiskey offerings use to their advantage. And given the other options at this price point, there are definitely better spirits available to scratch your rye whiskey itch."

Fighting Cock Bourbon — also called the "kickin' chicken" — makes the regrettable bourbons list not because it's overpriced. In fact, it's just the opposite. This bottle of 103-proof whiskey is affordable, retailing for around $20 for 750mL (so you're not really gambling your grocery money if you invest in a bottle). It's also flavorful, for the most part.

The problem is that, as one taster states, this bourbon is excessively sweet, without much complexity (via Distiller). Bourbon for the Masses adds that it's an incredibly thin whiskey and that there's nothing special about it (Redditors also echoed this sentiment, claiming that Fighting Cock Bourbon leaves much to be desired). The Whiskey Shelf even compared it to Larceny. Well, that's not good.

Do you know what happens to mediocre, boring bourbons? They usually disappear into cocktails or mixed drinks. It's sad but true. Ultimately, Fighting Cock Bourbon is just a boring, blah booze. It's not memorable. It's just sitting there, complacent, without much fight in it at all.

Rebel will make you want to rebel against the Kentucky bourbon distillery that makes this juice (that's Lux Row Distillers if you were wondering). Until recently, this bourbon was known as Rebel Yell, but it recently dropped the "Yell," perhaps because the old name was associated with the Confederacy (via Reddit).

Reviewers on Flaviar state that the juice is weak with little flavor, with a hint of mud in the background. One Distiller reviewer says, "nose is ethanol and nail-polish remover." Sounds tasty, doesn't it? This bourbon is an award winner (Double Gold at the 2016 San Francisco World Spirits Competition and Platinum at the 2018 SIP Awards). So you'd think that this boozy elixir would, you know, at least have some nice legs on it. Apparently not, because it's also pretty thin.

Thirty One Whiskey says that using it as a mixer doesn't really help much, so if you're shopping for affordable, bottom-shelf bourbon, do yourself a favor and don't be a rebel.

Brought to you by the Lexington Brewing and Distilling Company (not to be confused with Lexington Bourbon, the ones who brought you the bottle with a horse on it), Town Branch Kentucky Straight can only be described as a waste of money. One Redditor said Town Branch's unpleasant flavor earned it the nickname "hand cleaner." Interestingly enough, the company was also bottling and selling hand sanitizer during the pandemic.

Some reviewers on Flaviar noted that it had a rather off-putting aftertaste, and the word harsh came up multiple times. So unless you're interested in dropping $35 to $40 for a pretty bottle that happens to be filled with unpleasant whiskey, don't do it. Don't fall prey to the fancy packaging. You're better than that.

The Lexington Brewing and Distilling Company makes beers, hard teas, and canned cocktails in addition to its bourbon line. Judging by how utterly unpalatable the Kentucky Straight Bourbon is on its own, maybe the company should stick to beer.