Top 5 Olde-Timey Cocktails You’ve Never Had!

Welcome back to a food Friday. Even though we aren’t dealing with food today, this list will provide perfect ideas for your weekend. Today’s list is Top Five Olde-Timey Cocktails You’ve Never Had. Most of these drinks people have heard of, but rarely order when out. I know that its always easier and always more of a sure thing and always cheaper to just order a Miller Lite at a bar, but after making this list, I am going to try every single one of these drinks!

My guest today is Anna Sturgeon. Anna was nice enough to hire me for a job out in California. She is, for some reason, a huge Cincinnati Reds fan. We here at the Top 5 don’t hold that against her because if we made a Top 5 Shortstops in baseball, Brandon Phillips would easily be on it. Anna came up with this list on her own an submitted it to me and I couldn’t have been happier to make my list to correspond. Here is what Anna has to say and her list to follow:

I credit and thank “Mad Men” for the resurgence in popularity of the classic cocktail. I know it’s hard to beat the image of pounding Jager Bombs until you throw up on your shoes, but nothing is classier than knowing a good cocktail. You might have heard of some of these, but until you experience their definitive blends, you can’t discount these classics.

5) Tom Collins – The perfect way to describe this often discussed but seldom drank cocktail is carbonated lemonade meets gin. The perfect summer cocktail, it is both fizzy, sweet and stiff. The name of the drink is a little more than convoluted and I’m sure back in the days before Netflix and Pinterest were available to distract the masses, people thought it was a total gas to name a cocktail after a prank that wouldn’t even stand up to Punk’d criticisms. Back in the late 1800’s people would begin a conversation saying that Tom Collins, a cheeky bastard, has started a rumor about them, and urge the rumored to seek Tom Collins out. After a flurry of searching, the teller of the tale would laugh at the gullible mark, who would feel foolish. Yeah, I don’t know what that has to do with gin.

Plus, what’s not to love about a cocktail recipe that instructs you to drink it while it is “lively”

Jerry Thomas’ Tom Collins Gin (1876)
(Use large bar-glass.)

-Take 5 or 6 dashes of gum syrup.

-Juice of a small lemon.

-1 large wine-glass of gin.

-2 or 3 lumps of ice;

Shake up well and strain into a large bar-glass. Fill up the glass with plain soda water and drink while it is lively

Tom Collins

4) The Old-Fashioned – The name itself oozes old cocktail charm. The mixture of delicious bourbon, whiskey or brandy (bourbon is really the only way to go) is cited as the originating the term “cocktail,” an 1806 newspaper wrote that it was a “potent concoction of spirits, bitters, water and sugar.”  Don Draper’s cocktail of choice, it is not for the faint of heart, the bitters are a tough hang and the super-sweet of the maraschino cherry can be overwhelming. But a perfectly made Old-Fashioned can be perfection in a glass.

Old Fashion (1903 recipe)

Use old-fashioned cocktail glass. Sugar, 1 lump. Seltzer, 1 dash, and crush sugar with muddler. Ice, one square piece. Orange bitters, 1 dash. Angostura bitters, 1 dash. Lemon peel, 1 piece. Whiskey, 1 jigger. Stir gently and serve with spoon.

Don Draper with an Old Fashioned.

3) Singapore Sling – Fresh pineapple juice, Cherry Heering (so old fashioned you’ve probably never heard of it), Benedictine (ditto), and gin. The perfect summer cocktail, it’s creamy to the point that people often thing there is a dairy component added, similar to a Pina Colada. Invented sometime before 1915 by Ngiam Tong Boon, a bartender working at the Victorian hotel Raffles Hotel Singapore, it has become the signature drink of the hotel and quickly became a shadow of its former self with pre-mixed juices but the resurgence of old time cocktails has allowed this former glory to shine again.

The Recipe: Combine in a tall glass: 1.5 oz London dry gin (Beefeater or Tanqueray), 1.5 oz Cherry Herring or Bols cherry brandy, and .5 oz fresh-squeezed lime juice. Add ice, stir, and top off with 1 oz chilled seltzer. Float .5 oz Plymouth sloe gin over the top, stick a straw in it, and garnish with a lime wheel perched on the rim.

The Double “S”

2) Rob Roy – Created back in 1894, this was also made at a hotel bar, the Waldorf Hotel in NYC. This embodies everything a classic cocktail needs – scotch, vermouth, bitters and a maraschino cherry. Extremely similar to the Manhattan, the largest difference is that Rob Roy’s are created with Scotch rather than rye or now more commonly made with bourbon or Canadian whiskey. The drink is so simple but can be altered to be made sweet, dry, or perfect. The standard Rob Roy is made with sweet vermouth, so there is no need to specify a sweet Rob Roy when ordering and it is often garnished with a maraschino cherry whereas a dry Rob Roy is made by substituting dry vermouth for the sweet vermouth and topped with a lemon twist. The last and less common version is the aptly named perfect Rob Roy is an equal combination of both dry and sweet vermouth. Created in honor of the opera Rob Roy, this is a cocktail that will make even the most pallid day seem classier.

-1 1/2 oz Scotch

-1/4 oz sweet vermouth

-Angostura bitters to taste

maraschino cherry for garnish


-Pour the ingredients into a mixing glass with ice.

-Stir well.

-Strain into a chilled cocktail glass.

-Garnish with a cherry.

Rob Roy

1) Gin Ricky – My all time favorite drink. Refreshing and drinkable, this is little more than fresh lime juice and gin with a bottle of bubbly soda water waved beside it. Second only a glacial runoff, the Gin Rickey is a peerlessly cool, dry drink. Gin Rickey was named for Missouri politician “Colonel Joe” Rickey, who invented this concoction during the hot, muggy summer of 1883 in Washington, DC while he was busy shit-disturbing and making bets about who would become the newest Speaker of the House. I’m not sure if it is Col, Joe Rickey’s gentlemanly gambling ways that make me love this cocktail so much or just its crisp refreshment, but the shout-out in The Great Gatsby also doesn’t hurt.

Gin Rickey

-Put 3 or 4 ice cubes into a tall glass.

-Squeeze in 1/2 lime and drop in the rind.

-Add 1 1/2 oz gin.

-Top off with chilled club soda or seltzer.

Gin Rickey

Amazing list! Well done Anna. LIKE A BOSS! Here is my counterpart:

5. Old Fashioned – Like Anna said above, this is a classic. Mad Men is a show that has completely changed the way TV has done period pieces, and one of the things it has done is make smoking and drinking cool again. And drinking an Old Fashioned must be pretty cool. I feel like I want to go to a bar right now and order one…then I realize I don’t have $19 to spend on a drink. CURSE YOU DON DRAPER!

The Old Fashioned

4. Sazerac – I picked this drink for one main reason…for the one ingredient in it that was banned for a long time. That one ingredient is Absinthe. Although you only “swirl the glass with the Absinthe”, that seems good enough for me to make this list. I have always been fascinated with Absinthe and the history of it since College when I found out about Oscar Wilde’s obsession and thoughts with it. Oscar Wilde has been quoted as saying, “What difference is there between a glass of absinthe and a sunset?” and “After the first glass [of absinthe] you see things as you wish they were. After the second, you see things as they are not. Finally, you see things as they really are, and that is the most horrible thing in the world.” Not to mention Absinthe is a crazy cool looking liquid…its naturally GREEN! Alas, with most drugs (and that is what alcohol is) people started to blame the use of it on violent crimes and as early as 1898 countries started to ban the use of Absinthe. The USA banned it in 1912. Even though you can now get in some parts of the world again, I don’t think it will ever be as Oscar Wilde had it. Too bad.

-1 teaspoon of sugar syrup
-3 dashes of bitters
-2 – 2.5 ounces whiskey

Fill small old fashioned glasses with ice and set aside to chill.

Stir the above ingredients with large ice cubes until thoroughly chilled. Empty the old fashioned glasses and swirl a dash of absinthe in each one – discarding any left over liquid. Strain the liquor into each chilled and swirled glass. Twist a peel of lemon over each glass and drop it on top as a garnish. Serve with a small glass of ice water on the side as a chaser.

Sazerac (including the bottle of Absinthe)

3. Manhattan – These next two drinks I just personally believe are as classy as it can get. For this one, you must be a whiskey lover. I am not a huge whiskey guy, and I would prefer a the number 2 drink on this list over this, but both just seem way too classy to not have back to back.

-1 part Italian vermouth
-5 parts whiskey
-1 dash angostura

Stir (never shake) the above in a bar glass with ice. Strain in to a cocktail glass and garnish with a single maraschino cherry – if it does not have a stem, place it on a toothpick.


2. Martini – Now, I have never had a martini before (that’s why it’s on this list), but like most of you, I think of one thing when I hear it…James Bond. However, doing some research into the drink, I find that James Bond is probably an idiot when it comes to drinks. The main reason is, you NEVER shake a martini. That isn’t just because that is not the classy thing to do, you just don’t because it is a white liqour drink. All white liquor drinks are stirred because shaking introduced bubbles, introduces too much water, and the shaken wine (vermouth) makes the final result murky. Incidentally, if you absolutely must have it shaken – it is not a Martini, it is a Bradford. Now, a Bradford still sounds super classy, but no where near the level of class as the sound of a Martini.

-1 part Lillet Vermouth (French)
-7 parts best quality gin (Tanqueray No. 10 is recommended)

Stir the ingredients in a bar glass and strain into cocktail glass. Add an olive on a toothpick.


1. Tom and Jerry – To be completely honest, this drink is completely nostalgic for me. My grandpa used to make these at Christmas and I was never old enough to enjoy one before he died. I honestly don’t even know what one is or how to make one (Any of my aunts, uncles or parents reading? Please put Bill Leinenkugel’s recipe if you know it down in the comments). All I know is that he loved them and every Christmas, he would sit down in the basement playing blackjack with anyone who bellied up to the table and he would deal those cards with a smile on his face sipping those Tom and Jerrys. He would teach his grandkids how to play until they were able to play for themselves, then the choices were all theirs. And he loved taking money from anyone he could sitting next to the fire in the fire place. I wouldn’t be surprised if those were some of the happiest memories of his life. I know they were some of mine.

Tom and Jerry

That does it for this week of the Top 5. This also concludes the first month of this site being up! Thank you to everyone who reads it daily or checks it once in awhile. Thank you to all the guests that have taken some time to make a list and submit it to me. Remember, anyone can submit a list using the user ideas tab up at the top menu of the website. Leave what you will be trying (or just what you will be drinking) this weekend down in the comments and have a safe and wonderful weekend.