Well if you always see him at the bar, maybe you can go sit next to him or something...Look..nonchalant for a bit and then tell him that you see him there a lot and ask if he lives nearby...Strike up a casual conversation that would not be awkward next time you saw him...Then next time you can talk a bit more and such and in no time everything will be good...If you are too shy for that, you can even sk the bartender or someone else his story, since everyone seems to know him...Good luck!..

Why on earth would you chat up his friends? If he's seated at the bar, you could just walk up to him and order a drink. And then just say hi to him. There's really no big form of rejection there because you'll be waiting for your drink. He will either talk to you, or not. And when your drink arrives if he's not talking to you -- you just walk off back to your friends. No harm. No shattered ego...

Is it just me or does this guy NOT sound like a prize ?..
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First get the 411 from the bartender, next get the bartender to engineer an encounter, after which get thee to counselling to figure out why you are attracted to these types of guys. lol...
Good Luck...
-Carlos..

Can you somehow start a conversation with him without actually asking him out?..I've had success talking to guys about the games that are on at the bar -- totally innocuous, and a good way to break the ice...
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Another way is to stand near him when you order your drink, then make a remark about the song that's playing or what the bartender's wearing...You'll be able to tell pretty quickly if the guy is interested if he tries to prolong the conversation...And if you get the idea that he doesn't want to talk, there's no way you can really be embarrassed -- I mean, you just made a very offhand comment...
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Good luck!..

Ahhh, the allure of the brooding loner...well do I know it. You're afraid he might just snarl at you, sunk too deep in his own pain to recognize the suffering of a fellow human being, or the pulsing desire of that human being to lift him out of his doldrums, or the firm, creamy-white decolletage of that human being, so appealingly buttressed by a black PVC bustier... ..
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Ahem...Anyway. You might try taking a page out of his own book of aloofness. Sit at the bar for a while yourself, alone -- being surrounded by chatty friends will make you look shallow and uninteresting...One night, send him a drink -- "from the woman in black" or "from the dark lady across the bar" or something equally mysterious (I'm guessing from your Q and your username/avatar that you don't frequent sports bars, and that such a move might be appropriate for your milieu)...Then let him reciprocate, or approach you to thank you. After that, let your charm -- and your decolletage -- lure him all the way in. Good luck!..