A Gentleman's Bar

You'll get funny looks from the liquor store people, but you might want to just buy a shitload of miniatures to start out with and sample all of the more general categories of cocktails/spirits before investing too heavily in any particular one.

That said, as far as manly drinks go, I tend to consider the classics the pinnacle. Old Fashioneds, martinis (WITH GIN- it's not a martini just because you put vodka in a martini glass), Sidecars, Sazeracs, G&Ts etc. Manhattans should probably be on the list too but sweet Vermouth turns my stomach.

Most importantly, Scotch. Scotchy Scotch Scotch. IMHO Scotch is the manliest of all drinks.* Single malt is of course best, but cheap blended shit is every bit as manly in my estimation.

Also get some glassware. It doesn't have to be great but at least get one or two martini, highball, and tumbel (Old Fashioned) glasses. For me at least the proper glass is a huge part of enjoying a drink.

* Exhibit A:

Exhibit B:

For what purposes are you purchasing all of this? Your own consumption, social occasions with friends, wild college parties, ... ?

Regardless, this is what I did at one point shortly after graduating from undergrad. I bought a little of everything and basically made a fully stocked home bar. Then I went and got the Four Seasons bartending guide and just started trying out different drinks - works great at parties when you can have your guests pick out random drinks from the books. Turns out some of those "manly" drinks taste like crap.

However, if you're just having wild college parties, just buy a lot of Jack, Smirnoff, tonic, cola, etc, because it won't really matter.

Although I don't drink them much myself, I find it hard to imagine a complete bar without vodka and rum, especially if you ever allow ladies into your gentleman's bar.

If your Scotch purchase is going to be single malt, I would suggest something approachable to as many as possible. This will probably mean a Speyside, so think Craigganmore or Balvenie. The Bal double cask wood aged is pretty reasonable in price and no one should turn their nose up at it.

The poster above is correct, you need rum and vodka. For vodka, I'd suggest the Kirkland bottling of Grey Goose available at CostCo. Hard to find a better deal and I bet you'll be the only kid at the frat house with CostCo vodka

Interesting... so is it the same stuff as regular Grey Goose?

It's produced in France. I did some side by side taste tests and out of 10 people, nobody could tell the difference. I think it's a fucking steal, although I'm more of a Stoli man myself, as $30 nets you 1.75l. The only problem is the bottle is so fucking big that you can't fit it in some freezers.

Wow... that's a helluva deal.

FYI: CostCo also has a Big Mac bottling, I think 18 or 19 year old. About $90. You have to watch what you are buying, but they have some slamming deals on wine too.

Rusty nail's are always good; drambuie and scotch (use a cheaper scotch - save the good stuff to drink straight up)

Rather than try to master a LOT of spirits and cocktails all at once, my advice would be to select just a few really good ingredients to make just a few amazing cocktails. Get a shaker, a quality lime juicer, a few nice glasses and enjoy the experience of preparing and serving to your lucky guests something really special.

You might want to start with a simple rum drink, like a Mojito, (a regular clear rum will do). use plenty of fresh lime juice, fresh mint, club soda and superfine sugar.

A premium, "top shelf" margarita (no mix!) (Get a premium tequila and make a "top shelf" margareta (fresh juice of one lime, 1 shot cointreau and 1 1/2 shot good tequila shaken and served up.) this way you really taste the quality tequila and the same tequila can be enjoyed straight, sipping, not shots. Shots are for the rot gut frat buzz juice stuff.

Maybe a nice Burbon drink, and again with really good burbon you can enjoy it straight, it's ideal for sipping.

You might even want to start with just one cocktail, get really good at it and then move on to another.

It would help if you made it clear what actual background and experience you have with liquor and cocktails. No offense, but it sounds like you're only going off your reading of "Manly Man" circle jerk threads/articles with no actual experience, which is going to result in your wasting a lot of money on things you'll probably never use. For example, B&B is really only servable on its own, and Drambuie is useless unless you like to sip it neat or make Rusty Nails, which are very much an aquired taste. You would do well to make a few outings to upscale restaurant or cocktail bars, look around the drink menus, and sample some of the cocktails available to see what you like. If you're not buying this bar to entertain, then you should plan on tailoring it around what you know and like, lest you end up with a bunch of unused bottles sitting on your shelf.

That aside, let me give you a basic short list of the essentials you'll find at any bar, and let you extrapolate/cut from there.

At the bare minimum, any bartender's speed rack (i.e. the most frequntly used liquors kept closely on hand in the well) should contain:

-Tequila (flexible here, I'd just go with a decent silver tequila, like Herradura, for example. Sauza Hornitos is a reposado with lots of bang for the buck. Be prepared to spend big if you want quality tequilas).
-Triple Sec/orange liqueur (Cointreau is ideal, but pricey; there's no shame in going with triple sec from a generic liqueur brand like Bols or Hiram Walker).
-Light Rum (Bacardi Silver is fine; other decent bang for the buck brands include Appleton, Barbancourt, and Mount Gay. There are other kinds of rums, but those are for when you have a more experience with rum.)
-Gin (self-explanatory, good and inexpensive brands include Beefeater, Bombay Dry, Boodles, and Broker's)
-Vodka (again self-explanatory. Avoid the marketing hype brands like Goose and Absolut. There are some solid and affordable lesser-known brands out there, like Boru, Finlandia, Monopolowa, and Wyborowa, for example.)
-Bourbon (You'd be wasting time splurging on an expensive single barrel brand at this point. Maker's Mark would be a fine pick. Also consider looking at American rye whiskeys if you want to be real old school about your cocktails.)
-Scotch (Dewer's, Johnnie Walker Black, and B&B are good blends for cocktails like Rob Roys and Rusty Nails. I'd go to a scotch bar and sample various single malts before splurging on a bottle of the more expensive stuff.)

Some of the essential mixers for a cocktail bar:
-Juice (orange and cranberry are essential, pineapple is important but not as much, and grapefruit is optional.)
-Soda/Tonic (I'd buy the little mini bottles so you can use them sparingly without worrying about everything going flat.)
-Coke/Sprite/maybe Ginger Ale
-Half and Half
-Bitters (Angostura is the most common variety.)
-Grenadine
-Rose's Lime Juice
-Sour Mix
-Sweet and Dry Vermouth
-Red Bull if you're trying to be trendy

Other common liqueurs that are useful to have around depending on your needs; you obviously won't need all of them. Also feel free to substitute the more expensive stuff like Bailey's with imitation brands:
-Amaretto
-Bailey's Irish Cream
-Chambord
-Creme de Cacao
-Creme de Menthe
-Frangelico
-Grand Marnier
-Kahlua
-Midori
-Peach Schnapps
-Southern Comfort

If you're looking to do a shot bar for your friends, here's what I go through the most of at work, though you'll find heavy regional biases (I'm from Houston FWIW):
-Apple Pucker
-Butterscotch Schnapps
-Flavored rums or vodkas (e.g. Stoli Vanilli, Bacardi O, Absolut Citron)
-Goldschlagger
-Jaegermeister
-Rumpleminze
-Tuaca
-Watermelon Pucker

I'm sure there's a lot more you can include, but this should be a fairly comprehensive list of what actual bars tend to stock, and you can work it out from there based on what you're looking for.

If you want to get interested in quality alcoholic beverages, don't neglect beer.

There's a huge range of excellent microbrews out there, locally produced and affordable.

If you're American (I'm assuming you are), you may want to look into breweries such as Rogue, Dogfish Head, Allagash, Goose Island, etc.

A big advantage is that you can buy 10 of the best beers in the world for the less than a bottle of decent Scotch.

No offense, but that's probably because they were poorly made -- by you and 90% of the bartenders in the country. So many of the mixers and the sodas are crap to begin with, so how can the drinks be expected to be any better?