Bourbon used to be so simple: A humble, economically priced spirit from Kentucky. You could drink it neat, or with ice, maybe even mixed with soda — it needn’t be fetishized. Over two centuries of existence, bourbon had its ups and downs, but it was always reliably there. Often less than 20 bucks a bottle too, whether you favored Jim or Jack or even one of the “Olds” (Crow, Grand-Dad, Weller).

And then the aughts came and bourbon lost its mind.

Distilleries began releasing bourbons that cost hundreds of dollars. Drinkers cleared them from store shelves. Black markets arose to sell those bottles online for even more money.

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Suddenly, the only bourbon anyone could find any more were those humble, economically priced Jims and Jacks and Olds that have always been there for us. In bourbon, the more things change, the more they stay the same.

These are the 24 moments that built an industry, helped it survive during troubled times, elevated it into the zeitgeist, and made it what it is today.

1785: Basil Hayden Brings Immigrants to Kentucky

A Catholic living in Maryland, Hayden was tasked with bringing 25 local families to Nelson County, Ky., to help set up a church community. Many of these folks were Scottish, Irish, and English immigrants, and many already had distilling in their blood. Hayden was also a distiller and today two bourbons are named after him, Basil Hayden’s and Old Grand-Dad.

1791: The Whiskey Rebellion Sends More Distillers to the Bluegrass

Treasury Secretary Alexander Hamilton puts an excise tax on whiskey — the first tax ever imposed on a domestic product by this new American government — to try to pay off the debts of the American Revolution. This angered many farmers in western Appalachia who often distilled their excise grain into whiskey. In turn, many of them moved to the tax-friendly havens of Kentucky and Tennessee.

1790s: Bourbon Accidentally Get Barrel Aged

Kentucky didn’t just have distillers, it also had exceptional Indian maize corn and access to limestone-filtered water. More importantly, it was located on the Ohio River, where barrels of this new-make corn whiskey would be loaded onto flatboats in Lexington and sent down to New Orleans. (Many claim that a Bourbon County pastor and distiller named Elijah Craig was the first to figure out that the cheapest storage method was to clean a fish barrel by burning the inside of it, then add the whiskey to it.) By the time the “bourbon” arrived in port 90 days later, the charred oak barrels had turned the liquid caramel in color, and made it a whole lot tastier.

1818: He Did the Mash, the Sour Mash

Though the inventor of this process is usually credited to Dr. James C. Crow (of Old Crow fame), its usage has been traced back further than that. In the early 19th century, distillers began “souring” their whiskey mash by adding back some of the acidic liquid strained from the previous mash, known as backset. This wouldn’t just inhibit bacterial growth, it would add to the flavor of the final product. Today, almost all bourbon is “sour mash,” with many even stating it on their labels.

1870: Old Forester Is Bottled

A former pharmaceutical salesman, George Garvin Brown, had a stroke of genius when he decided to sell his Old Forester bourbon not from barrels, but from sealed glass bottles instead. It was a savvy move; Old Forester has literally never been out of production since then, even during Prohibition, the longest-running bourbon in the U.S. today.

1897: The Bottled-in-Bond Act

But it wasn’t all high quality — many dubious bottlers and rectifiers would take their whiskey and add everything from prune juice to tobacco spit into their bottles of “bourbon.” Thus, a need for an assurance of quality arose and the legitimate distilleries lobbied congress to pass legislation. To get a “Bottled-in-Bond” designation, whiskeys had to come from one distillation season courtesy of one distiller at one distillery, then get aged in a federally bonded warehouse for at least four years, before being bottled at exactly 100 proof.

1919: Bourbon Finds a Prohibition Loophole

If there were a good two dozen distilleries in Bourbon County at one point, after ratification of the 18th Amendment, ironically, the county would never produce bourbon again. Meanwhile, six major Kentucky distilleries exploited a loophole and began making “medicinal” whiskey — in reality, simply affixing prescription labels to flasks of bourbon. (“Sick” Americans would have to have a doctor claim they were suffering from one of 27 ailments.) By the time the “Noble Experiment” of Prohibition ended in 1933, conglomerates like Schenley, Seagram, and National had acquired many family-run distilleries.

1935: “Pappy” Van Winkle Opens Stitzel-Weller

A traveling liquor salesman starting at age 18, Julian “Pappy” Van Winkle, with a partner, took over W.L. Weller & Sons in 1915 and immediately began producing stellar bourbon in conjunction with A. Ph. Stitzel, even during Prohibition. On Kentucky Derby Day 1935, Van Winkle’s first distillery, Stitzel-Weller, would open, eventually making waves for their uniquely wheated bourbon seen in products like Old Fitzgerald, Cabin Stiller, and Weller. When he died in 1965, who would have ever guessed that one day Pappy would be the household name of 21st-century bourbon?

1947: Frank Sinatra Starts Swigging Jack Daniel’s

Perhaps an apocryphal origin story, Sinatra would claim Jackie Gleason had told him that Tennessee whiskey was a “man’s drink.” He quickly became the brand’s biggest fan, flying a Jack flag at his house in Palm Springs and finishing an entire bottle of Old No. 7 every day, two fingers over three ice cubes in a rocks glass. Many say Sinatra turned this small Tennessee brand into literally the biggest bourbon brand in the world (yes, nerds, Tennessee whiskey is bourbon). In 2013, Jack Daniel’s returned the favor by releasing Sinatra Select, a limited, higher-end bottling.

1954: Jimmy Russell Clocks in at Wild Turkey

Some 66 years ago, on Sept. 10, 1954, a 19-year-old boy raised just six miles from the JTS Brown Distillery in Lawrenceburg, came to his first day of work sweeping floors. He would soon be mentored in the art of making the distillery’s Wild Turkey bourbon by the brand’s second-ever master distiller, as well as Ernest W. Ripy, Jr., the son of the original distillery owners. By the late-1960s Russell had the keys to the castle. As master distiller, the lovable “Bourbon Buddha” traveled the world as an ambassador for bourbon, finally seeing the fruits of his labor in the last couple of decades. Today, at age 86, Russell remains the longest-tenured master distiller in the world, still making some of the finest whiskey around, along with his son and fellow Wild Turkey master distiller, Eddie Russell.

1958: Maker’s Mark Creates the Premium Bourbon Category

Bill Samuels Sr. would famously zig when others were zagging, launching a premium whiskey in classy packaging at a time when people were moving away from bourbon. The gambit would eventually pay off. By the 1980s, the iconic red-waxed, square-shaped bottle was considered the industry’s Rolls Royce among a parking lot of Pintos. Bourbon tourists were visiting the Loretto distillery as early as 1968 and today many credit Samuels and Maker’s Mark with ushering in the current bourbon boom.

1964: Bourbon Becomes a “Distinctive Product”

Worried the rest of the world had eyes on stealing America’s homegrown product, in 1958 the Bourbon Institute was formed with the sole purpose of getting bourbon the same internationally recognized regulatory protections enjoyed by product categories like Cognac and Champagne. Lobbying Congress, on May 4, 1964 bourbon was officially recognized as a “distinctive product of the United States.” Bourbon could now only be produced in America (not just Kentucky as some internet commenters will have you believe), putting an end to Mexican-made bourbon.

1969: White Spirits Emerge, Light Whiskey Is Created, and a Glut Occurs

By the 1960s, white spirits like vodka and gin were taking over the bar scene, delivering a major blow to the bourbon industry. The distilleries came up with a plan to create an entirely new product to compete: Light whiskey, distilled to such a high proof it tasted like vodka. It was an abject disaster. By the early 1980s bourbon sales had plummeted, and plenty of barrels and bottles were sitting around with no one to buy them — a fate that collectors would one day regret as vintage bourbon from this era is now much desired.

1976: Wild Turkey Adds Some Honey

Cringe if you must, but another attempt to fend off white spirits and position bourbon as less of your “old man’s drink” was by adding flavors. Jimmy Russell was the first when he thought to make a liqueur by blending Wild Turkey with pure honey. It was a huge hit, and other bourbon brands would begin offering their own flavored concepts. This would eventually lead to fratty flavored whiskey sensations, such as Fireball and Skrewball Peanut Butter Whiskey.

1984: Single Barrels and Small Batches Arrive (but Only Japan Cares)

Wanting to impress Japanese consumers, the newly formed Ancient Age distillery asked its master distiller Elmer T. Lee to create a truly one-of-a-kind product. He hunted down some primo “honey” barrels from Warehouse H and bottled them as is. Blanton’s would be the world’s first commercial single-barrel bourbon — it was a sensation in Japan, though it would flop domestically. Still, it gave the other bourbon distilleries some new ideas. The year 1988 would bring Jim Beam’s Booker’s, a small-batch, barrel-proof offering. By 1992, the release of Jim Beam’s Knob Creek was starting to woo more and more neophytes into the bourbon world.

1994: Pappy Van Winkle Hit Shelves

In 1972, Pappy’s son, Julian Van Winkle Jr., started the Old Rip Van Winkle brand, selling bourbon he had acquired from Stitzel-Weller after its brands were sold off that same year. By 1981, his son, Julian Van Winkle III, was running operations, eventually selling 12- and 15-year-old Old Rip Van Winkles (bourbons that only existed due to the aforementioned glut). In 1994, he had the gumption to release a then-unheard-of 20-year-old bourbon, which he called Pappy Van Winkle, after his grandfather. It would immediately win acclaim across the country. Pappy Van Winkle 23 Year would come along in 1998, and the 15 Year Old would arrive in 2004.

1999: The Bourbon Trail Is Officially Created

With a renewed interest in bourbon, tourism began to take off and the distilleries wisely moved to capitalize on it, opening gift shops and offering public tours. As the Y2K drew near, the Kentucky Distillers’ Association registered a trademark and launched the official Kentucky Bourbon Trail. Initially, seven of the eight major distilleries were on it, and today eight more craft distilleries like Wilderness Trail are also included. The Bourbon Trail is said to have brought Kentucky 2.5 million tourists over the last five years.

2002: Four Roses Starts Selling Bourbon Again

A once venerable brand, in 1967 Seagram’s turned Four Roses into a blended whiskey, cutting it with grain neutral spirit and flavoring. And, yet, in Japan, it was still sold as a straight bourbon and was a huge hit. When Jim Rutledge took over as master distiller in 1995, he began lobbying his bosses to let Four Roses return to its former glory stateside. He finally got his wish when Japanese company Kirin bought the brand in 2002. The straight bourbon would indeed return to America, and by 2004 Four Roses was even selling single-barrel bottlings, offering drinkers a chance to try one of 10 mashbill-yeast recipes the distillery offers (something wholly unique in the industry).

2006: Willett Offers Single Barrels

Everything changed at Kentucky Bourbon Distillers when owner Even Kulsveen’s son Drew joined the family business in 2003. Almost immediately, he began taking the company’s incredible stock (more glut bourbon sourced from places like Bernheim, Heaven Hill, and even Stitzel-Weller), and releasing it as cask-strength, non-chill-filtered single barrels. Such well-aged and high-proof bourbons and ryes were almost unheard of at the time, and bottlings like Red Hook Rye and Doug’s Green Ink would soon become some of the most coveted American whiskeys of all time. Even today, Willett inspires a fanaticism among the cognoscenti matched by no other brand, not even Pappy.

2007: Parker’s Heritage and Other “LEs” Arrive

Buffalo Trace already had its limited releases like Van Winkles and its vaunted Buffalo Trace Antique Collection, and other distilleries would soon throw their own hats into the rarity ring. This Heaven Hill yearly limited edition release (or “LE” in collector parlance) would be one of the first to make its mark, named after the distillery’s beloved (and now-late) master distiller Parker Beam.

2007: Non-Kentucky Bourbons Appear

Lest we forget, Kentucky isn’t the only state legally allowed to make bourbon. And, as craft whiskey began ramping up in America in the mid-aughts, other states started taking a stab at it. One of the first was New York’s Hudson Baby Bourbon, produced by Tuthilltown Spirits in the Hudson Valley. Today, just about every state produces a bourbon or two, though, if you talk to a Kentuckian, they’ll tell you none of them are worth a damn. But we recommend tasting and deciding for yourself.

2012: The Black Market Emerges

Since bourbon had always been an everyman’s spirit, distilleries had often been skittish about overcharging for it. But, when everyone in the world wants Pappy Van Winkle, an MSRP of 80 bucks just ain’t gonna cut it. Thus, in the early 2010s a secondary market began to form, first ad hoc on eBay and Craigslist, before becoming a bit more organized via private groups on Facebook with names like Strong Water Showcase and BSM (Bourbon Secondary Market). Wheeling and dealing ensued and releases like George T. Stagg and Weller Full Proof started fetching closer to their true market value. Not everyone was happy, however; on June 13, 2019, Facebook shut down all secondary market groups.

2014: The Curtain is Pulled Back on MGP Madness

The industry’s dirty little secret was that many of these Iowa or West Virginia or Vermont craft “distilleries” weren’t actually distilling their own bourbons and ryes, but instead sourcing them from Midwest Grain Products (or MGP), a mega-factory distillery in Lawrenceburg, Ind. Luckily, MGP made quite good whiskey — and offered some of the oldest rye stock around — and helped brands like High West and Smooth Ambler attain stardom among whiskey geeks.

2020: Sticker Label Mania Foretells End Times

First, bars, retail outlets, and private whiskey groups started buying single barrel “picks” from the leading distilleries. Then, some of them began adding their own cartoonish decals to the bottle. Suddenly, merely having a 50-cent sticker on a single barrel pick of, say, Eagle Rare or Russell’s Reserve would magically turn it into something worth hundreds of dollars. The industry may not have fully jumped the shark yet, but, if you want to, you can probably buy a bottle with a shark sticker on it these days.