I'd start with Tie Fighter (but then again, that is what I started with!). Definitely start with something other than XWA though. XWA is good but it is a bit softer on the player and lacks some of the deep stress the others dramatically invoke.

I'd start with X-wing, Tie fighter and skip to X-wing Alliance. Unless you have some buddies I'd avoid XvT.

On reflection, I agree. I said above that XWA was better than TIE Fighter ... Having now replayed them both, I have to say that I now prefer TIE Fighter. When I originally played this in 1995, i didn't have any internet (ah how backward we were) and so couldn't get any play guides, and found it super hard. In 2015, with a full strategy guide available, it is much better. Awesome fun hooning around in unshielded craft ...

I started with TIE Fighter. It's got a very realistic story line and positions the player right where he should be - an insignificant soldier in a disposable machine. Only through continuous success and luck can he prove his value. Being able to blow up in 2 hits radically changed my view on life. O.o

All the critical posts vs. my suggestion seem to be ignorant of the fact that Balance of Power is included with GoG's verison of XvsTIE. THAT's the story/campaign I'm referring to (pretty sure I did name it), not the base game which is just the dull multiplayer designed missions.

Strewth! Balance of Power is the best storyline/campaign from the series for my money. Only TIE Fighter comes close.

For anyone with a hazy memory Balance of Power is the full-blown two-sided campaign that was an expansion to the original XvsTIE, and was made precisely because of the criticism of the base game not having any single-player friendly content.

Do not start with X-wing, just don't, it has a notoriously unfair difficulty curve, it took me years to complete the main campaign.

Start with Tie Fighter (CD-rom DOS version, the special edition does look prettier but it's a straight port and has some balance issues), first by doing the Combat Chamber missions (they are essentially the tutorial) and then the training simulator, only then start the campaigns ("battles"), possibly set on "easy" (by selecting it in the option menu accesed by using the ESC key).

X-wing vs Tie Fighter has a bit more nuance in the gameplay but it can be very difficult as many missions (not all) are designed to be played in coop by human players, they are playable in single player but they tend to be more difficult than the average Tie Fighter mission.

It's still mainly designed with coop in mind, especially the rebel portion of the campaign. Xvt works only with HOTAS systems that share the same USB port for all components (and even then you are limited to 3 axes and 20 something buttons), for the others (usually the more costly ones like the Saitek X-55, the thrustmaster Warthog or CH products) you will need to use the HOTAS mapping software and to a custom profile to make it work otherwise, with "mix and match" HOTAS systems like the ever popular Thrustmaster T-16000 and CH Pro Throttle combo you'll need some external utility like Joy2key to get all components to work with the game.

Of course the Thrustmaster HOTAS X works without issues as throttle and stick share the same USB port, and it should be the same for the Saitek X52.

Though it really is a game that seems to be made to be played with one, particularly the speed vs turning speed mechanic becomes incredibly immersive using a HOTAS.

I would say start with Tie Fighter. Enter the game and do the training missions, then jump to X-wing. The training missions on Tie Fighter are great. They assume you know absolutely nothing and teach you from scratch how to handle each system on the craft. The X-wing historical missions don't do as good a job at teaching as the Tie Fighter game does. Some of the Tie Fighter training missions were copied exactly to X-wing vs Tie Fighter.

Agreed. Also, unlike all the starfighters in X-Wing, the TIE fighter/interceptor/bomber don't have shield systems, so that's one less thing to have to try to juggle and manage at first. By the time you're doing TIE advanced/defender missions, you should have the hang of managing laser recharge rate/engine speed, then you can start learning shield arcs and transferring laser energy to shields and vice versa.

The controls are nearly identical in both games (except I don't think you can target individual ship components in X-Wing), so you can configure joystick/gamepad the same in each and it feels like you're playing the same game.

I had the same issue (though I did play the games back in the 90s). Actually, I would recommend the following order:

X-Wing (DOS CD version)
TIE Fighter (DOS CD version)
X-Wing Alliance.

The reason to start in this order is that the games get continually improved in handling and available controls. Playing X-Wing after having played TIE Fighter I often encounter problems in handling: not being able to match the target's speed, not seeing where the target is (if it's in a distance), not being able to check what goals I achieved... so it is a better experience having these features becoming available with every subsequent game.

Oh yeah. Do avoid XvT and the 98 versions of XW and of TF.

X-wing is too unfair for a newcomer, he should start with Tie Fighter, doing the Combat Chamber missions first.
I get that X-wing has a rougher gameplay but he risks to be turned off the series entirely, it's actually easier to get to X-wing after having played Tie Fighter in my experience, while Tie Fighter added a few things a lot of gameplay mechanics are the same and Tie Fighter does a far better job in teaching a new player how to use them.

I don't get the hate against X-wing vs Tie Fighter, yes, for a newcomer may be tough (not as tough as X-wing though) and the presentation is drab compared to the other games in the series but it's still a great game even played in single player, also the GOG.com version has the expansion that adds a campaign for both the rebels and the imperials.

But yes, the DOS cdrom version of the original is the best.

Not really. I'd say, X-Wing is relatively fair if you do it the following way:
- Manage the Pilot Proving Ground
- Make the Combat Missions for X-Wing, Y-Wing and A-Wing
- Finish the Tours of Duty I-III
- Make the Combat Missions for B-Wing + Bonus Missions
- Continue with Tours of Duty IV-V

TIE Fighter will be actually more rewarding once you mastered X-Wing with its imperfections.

The problem is that the X-wing historical missions don't actually explain how to play the game to a newcomer, the only difference with the tours of duty is that when you die you don't risk to lose all your records, and the few explanations in the briefings are generic and don't go into as much detail as they should.

In Tie Fighter instead you get both detailed briefings and in-game instructions in the combat chamber missions and the campaign is much less punishing.

I never managed to get far in the X-wing Tours of Duty before beating Tie Fighter twice and I also had to consult a strategy guide because I got repeatedly stuck (which never happened with Tie Fighter), and I stress that I had the game for years before starting Tie Fighter, and this even after mastering both the pilot proving grounds and having beaten most historical missions.
There were several aspects of the game that just weren't clearly enough explained and I never understood until they were explained to me in the Tie Fighter Combat Chamber missions

Hell, X-wing vs Tie Fighter is a better choice than the first X-wing as the first game to play for a newcomer because at least it has a tutorial even though it's hard as nails compared to Tie Fighter.

And besides, it's not like you have a strong continuity like in the Wing Commander series, the games plot-wise could be played in any order.

This thread was started over a year ago, and since then the DOS CD-ROM versions of X-Wing and TIE Fighter have been added to the GOG releases. Most players consider these to be the best versions, so definitely go for those over the original floppy versions or the Windows versions.

As for what order to play the games in, I always recommend playing in release order if you're planning on playing the whole series. But if you're only going to pick one, then you have a few choices. Please note that I've played all the games except X-Wing, something I plan to correct soon!

TIE Fighter is my favorite game of them all. Absolutely fantastic, if on the older side compared to the others. The DOS CD-ROM version contains two expansions, the second of which I never quite finished, so I have to go back and do that soon.

X-Wing vs. TIE Fighter: Balance of Power - I found these missions absurdly difficult and never got anywhere in either campaign. The game has nice tutorials but I think these campaigns were designed for co-op play and are too hard in single player. I do plan to return to them someday now that they're here on GOG though.

X-Wing Alliance - Newer and prettier, and probably a bit easier for newcomers, but I didn't like the campaign nearly as much as TIE Fighter. Still good though. Possibly the best choice if the earlier games seem to daunting. One cool thing is that it casts the player as a freighter pilot for his family business before signing up as a rebel fighter pilot, so you get to fly Corellian transports (less-cool versions of the Millenium Falcon) in addition to X-wings and other fighters, and have to do missions for your family as well as for the rebels. Gives a little more personality to the player character.

That's basically the same thing everyone else said I guess. Again, I haven't played X-Wing but everyone says it's rougher and can get very hard. Still worth starting with it if you want to experience the whole series, just feel free to give up and move on to TIE Fighter if it's too annoying.

Didn't think somebody would answer this thread anymore. Looks like I was wrong.
Thanks for the extensive answers though! Gonna read them later today :)