Imagine a pirate. Most people picture a man. Grace O'Malley was a notable exception. Known as the "Pirate Queen," in the late 16th century O'Malley was a powerful leader who fought to keep her Irish territories free from English rule. Ezra Star created the Grace O'Malley cocktail centuries after O'Malley made her mark.

1.5 ounces Irish whiskey
1 ounce Mr. Black coffee amaro or Kahlua
.75 ounces orgeat syrup
.5 ounces super simple syrup
Juice from 1/2 lemon

Combine in a shaker without ice (this is dry shaking, see below), shake as if you're fighting for your freedom, and strain into a highball or Collins glass over crushed ice. Grated nutmeg and/or lime wheel garnish optional.

Using Irish whiskey in the Grace O'Malley is key, just as it is in other Irish cocktails such as the Tipperary and the Irish Coffee. Mr. Black coffee amaro, used in drinks such as the Blackjack, can be tough to get, but it's worth it. Kahlua is a sweeter and more accessible substitute. Orgeat syrup, a key component of drinks such as the Mai Tai, gives the Grace O'Malley a vague tiki vibe. If you want a stronger, less diluted Grace O'Malley, combine the ingredients in a shaker with ice (this is wet shaking), shake, and strain into a chilled glass without ice. If you like the queen theme and whiskey, try my Whiskey Queen.

Do you like pirates? Queens? Both? The answer doesn't matter because you'll be glad you became acquainted with the Grace O'Malley.

When I use the word "loaded" here it's a non-sexual double entendre. Monte Carlo, part of the city-state of Monaco, is loaded in that it has a ridiculous amount of money. The Monte Carlo cocktail is loaded in that it can make you very drunk if you're not careful. Making its grand entrance in 1948 in David Embury's book The Fine Art of Mixing Drinks, the Monte Carlo is simple and sophisticated.

2 ounces rye
.5 ounces Benedictine DOM
1-2 dashes aromatic bitters

Combine in a mixing glass with ice, stir as if you're suave and rich enough to gamble in Monte Carlo's legendary casino (think James Bond in Goldeneye), and strain into a chilled glass, preferably over a large ice cube.

The Benedictine DOM, a rich French herbal liqueur used in drinks such as my Whiskey Queen, is the key ingredient in the Monte Carlo or its variations. Depending on your perspective, the Benedictine substitutes in for the super simple syrup in an Old Fashioned, or the sweet vermouth in a Manhattan. How dry or sweet you prefer the Monte Carlo depends on the ratio between the rye and the Benedictine. Not into rye? Use bourbon (a Kentucky Colonel), reposado or anejo tequila (a Monte Carlos), or some other aged spirit.

Want to gamble like a Millionaire? A Monte Carlo will make you feel loaded.

"The bitch is dead" -- this is what James Bond icily utters when he learns of the death of Vesper Lynd, the woman who broke his heart. In Casino Royale (both the novel and the movie starring Daniel Craig), Bond falls in love with Vesper before he learns she is a double agent. All of this happens after he creates a cocktail in her honor.

3 ounces gin
1 ounce vodka
.5 ounces Lillet Blanc

Combine in a shaker with ice, shake with the fury of Bond exacting vengeance, and strain into a chilled glass. Lemon peel garnish.

Bond’s original creation is not far removed from a Martini, either the original or his version. Bond's Vesper calls for “three measures of Gordon’s, one of vodka, half a measure of Kina Lillet.” Gordon’s was and is a popular gin. Use whatever gin you prefer or have on hand.  Kina Lillet was a French aperitif wine.  It no longer exists under that name, but with a new formula it’s now known as Lillet Blanc. As you would with vermouth, make sure the Lillet Blanc is fresh and keep it in the fridge. If you can't find Lillet Blanc, dry vermouth is a good substitute. Bond never specifies the vodka brand, which amuses me because in popular culture he forever will be associated with vodka. If you or your guest is not a fan of gin (like I once was), adjust the ratios of gin and vodka.

The Vesper is a big cocktail because it contains four ounces of high proof alcohol.  Go Bond or go home.

Blessed with a sunny disposition, Charlie always was excited to see me when Ms. Cocktail Den and I visited our friends who owned him. While staying at their house during a stressful basketball tournament, Charlie calmly sat by my side as I watched my team battle for the title. I deemed him my emotional support dog. Charlie died last year, so I created this cocktail in his memory.

1.5 ounces vodka
.5 ounces Cointreau
.5 ounces honey syrup
Juice from 1/4 orange
1 dash orange bitters

Combine in a mixing glass with ice, stir with a calming and positive vibe, and strain into a chilled glass.

Vodka is a blank canvas for cocktail artists. Given its namesake, the Charlie had to be on the sweeter side, so I added a liqueur (you can use a different triple sec if you prefer) and honey syrup, a key part of the Bee's Knees and the Brown Derby. Honey and orange work well together, and here the orange juice (use fresh squeezed if you can) and orange bitters keep the Charlie from being aggressively sweet.

Want the cocktail equivalent of an emotional support dog? The Charlie is there for you.

Alliteration happens when you emphasize the same sound or letter in consecutive words. Typically alliteration involves the beginning of words. An easy and tasty variation on the classic Daiquiri, my original Daiquiri 43 puts the emphasis at the end of them.

2 ounces light rum
.5 ounces lime juice (1/2 lime)
.75 ounces Licor 43
2 dashes Peychaud's bitters (optional)

Combine in a shaker with ice, shake with rhythmic emphasis, and strain into a chilled glass. Lime peel or wedge garnish optional.

The Daiquiri 43 simply substitutes Licor 43 for super simple syrup (see what I did there?). Licor 43, an indispensable part of the 43 Up, is a slightly sweet Spanish spirit (I can't help myself).  Among other things, I taste vanilla in it, and it complements the rum nicely. Licor 43 is not nearly as sweet as sugar, and it definitely makes the Daiquiri 43 boozier than its ancestor. Using bitters such as Peychaud's (you also could try tiki or Angostura) adds some intriguing complexity to the Daiquiri 43, and so does using aged rum instead of light rum.

So get the ingredients for a Daiquiri 43, and have yourself a damn delicious derivation of a Daiquiri!

In some theologies, purgatory is the state after death before some souls ascend to Heaven. It's also the title of the second book in Dante's Divine Comedy (one of my favorite college classes was about The Inferno). Dante Aligheri in Florence created one of the most famous pieces of Western literature, and Ted Kilgore in Missouri who created the Purgatory cocktail in the mid-2000s.

2.5 ounces rye
.75 ounces Benedictine DOM
.75 ounces green Chartreuse

Combine in a mixing glass with ice, stir while contemplating where your soul might go (mine will travel in the bar car), and strain into a chilled glass. Lemon peel or wedge garnish optional.

Make no mistake, the Purgatory is a powerful drink. Those who are new to cocktails might have one and think they have descended into one of Dante's circles of Hell. The spice in the rye may make you think of Hell, and the silky sweetness of the Benedictine DOM may make you think of Heaven. The rye stands up to the Benedictine DOM, used in drinks such as the Honeymoon or my Whiskey Queen, and the 110 proof green Chartreuse, used in drinks such as the Bijou and the Last Word. Combining two herbal liqueurs from French monastic orders looks strange, at least it did to me. Have some cocktailian faith. You'll find they work well together in the Purgatory.

Regardless of whether you're religious, agnostic, or atheist, warm your soul with a Purgatory.

Leaving a lasting impact in fields such as art, science, and literature, the Renaissance was an important era in Western history. The cocktail renaissance (French for "rebirth") began in the early 2000s. The genesis of the Renaissance cocktail is unclear, but I discovered this version in Difford's Guide.

1.5 ounces cognac or brandy
.5 ounces sweet vermouth
.25 ounces Lupo limoncello
2 dashes peach bitters

Combine in a mixing glass with ice, stir with the joy of being revived or reborn, and strain into a chilled glass, preferably a coupe. Orange twist garnish optional.

Courtesy of the cognac, a key part of the Burnt Fuselage, the Renaissance has a spirited start. You can use brandy instead, as it's also derived from torched Dutch grapes. The sweet vermouth and limoncello soften the cognac's punch. Peach bitters are unusual, but as with the Whiskey Queen, they give the Renaissance a nice finishing flourish. If you need a quick substitute, try orange bitters. The drink has no connection to my Bourbon Renaissance, which is a little bit sweeter. Want to pair the Renaissance with modern music?  Try anything by the Rebirth Brass Band or Revival by the Allman Brothers.

I like to think I'm a modern Renaissance man (I'm not). Are you a Renaissance man or woman? Regardless of the answer, having a Renaissance will leave you enlightened ... and maybe reborn.

Everyone has a soul. Some of us have rhythm, some don't (if you've ever seen me dance, you know I'm in the latter category). Describing it as the love child of a Manhattan and a Sazerac, Greg Best in Atlanta created the Rhythm and Soul approximately 10 years ago. My fellow cocktailian Michael Bounds, who created the Ides of March, introduced me to the Rhythm and Soul.

2 ounces bourbon or rye
.5 ounces sweet vermouth
.5 ounces Averna
2 dashes Angostura bitters
Teaspoon of absinthe

Coat the inside of a chilled glass with absinthe, combine the other ingredients in a mixing glass with ice, stir with soulful rhythm, and strain into the chilled glass. Lemon peel garnish optional.

Best uses bourbon as the base spirit, but Bounds and I agree that to have the true soul of a Sazerac, rye should be the base of a Rhythm and Soul. Use the whiskey you prefer. Best calls for Carpano Antica as the sweet vermouth, and I wholeheartedly agree. It is pricey, but it is worth every penny. Averna, the Sicilian amaro used in the A Thief In The Night, works really well here. If you even remotely like either the Manhattan or Sazerac, you'll definitely like the Rhythm and Soul.

Move to your own beat, and get yourself some more Rhythm and Soul.

The Martini has been so famous and popular for so long, it should have a history as clear as it looks, right? If someone served you a Martini as murky as its history, you'd send it back. Its history is a mystery. Combining gin and vermouth in drinks such as the Martinez wasn't unusual in the 19th century. As time went by, the drinking public began to favor drier gins, and by 1896 what we now know as the Martini mixed dry gin and dry vermouth with an emphasis on the gin.

2.5 ounces gin (sorry James Bond)
.5 ounces dry vermouth
1-2 dashes orange bitters

Combine in a mixing glass with ice, stir (sorry again Mr. Bond), and strain into a martini glass. Lemon peel garnish optional.

The world’s most famous fictitious Martini consuming Englishman drinks his with vodka (and shaken). The world’s most famous real Martini consuming Englishman, Winston Churchill, drank his with gin. Originally I only drank vodka Martinis, but since I found I like certain gins, I'm not as picky. Whatever you do, use fresh vermouth. I can't emphasize that enough. Feel free to experiment with how dry you like your Martini (more dry means less vermouth). Bitters aren't necessary, but they add a little zest to a clear, gin based cocktail. 

There's nothing mysterious about a Martini. All you have to do is savor one.

For such a consistently popular cocktail, the Manhattan doesn’t have a consistent origin story.  The only consensus is that it originated in New York City’s most famous borough no later than 1882. While the Manhattan Club may have created the cocktail (or at least took credit for it), some sources identify an unknown bartender at the Hoffman House bar as the creator. Surviving Prohibition and the changing tastes of the drinking public, the Manhattan deserves its reputation as a classic cocktail.

2 ounces bourbon or rye
1 ounce sweet vermouth
2 dashes Angostura bitters

Combine in a mixing glass with ice, stir with energy and style worthy of New York City, and strain into a chilled glass, preferably martini or coupe. Orange peel and/or Luxardo cherry garnish optional.

The Manhattan is a remarkably flexible cocktail. The 2:1 ratio between the bourbon or rye and sweet vermouth isn't set in stone. Depending on the whiskey's strength and the drinker's preferences, you may want to adjust the ratio. As with other drinks cocktails calling for vermouth, e.g. the Martini, make sure your vermouth is fresh. With the proliferation of bitters on the market, you can use different bitters and have equally spectacular results.

Can you have a lot of fun experimenting with the Manhattan? There's one way to find out.