Let's skew the paradigm somewhat. If you had a speaker that wasn't very good at reproducing the source, you would definitely be able to tell. Over time however, without a true AB comparison between live and listening to recorded sources, you may get familiar with the sound and not notice what you are missing. To look at this another way, I just had a bunch of people over for a BBQ on the 4th. A few people, who like music, came out and asked about my stereo. They then wanted to hear it. So we would come in for a private showing, as I called it. I left Pink Floyd, The Wall, in my player and this was my demo disc. The most repeated comment I got was "I have heard this song a million times, but never like this. I didn't even know it had some of those sounds." This did not mean the speakers or any piece of gear were "real" or live sounding. It simply meant they were capable of reproducing the source more accurately than what they had previously heard. Granted, this was a studio recorded album, not a live rock concert.
Back to the original question. As markw stated, "real" is somewhat conjectural. But to get as close as possible, you need a speaker with a flat frequency response, IMO, and the ability to cleanly reproduce the recorded material. The gear you pass the signal through, plays a part in this as well. If anything in the signal path colors or influences the source in any way, you will get farther from the original or "real".
After that, it's all a matter of how the source material is generated, recorded or produced. Could a speaker reproduce an indistinguishable sound? I say yes. Sound, after all, is no more than a vibration. The "real" question is, can an indistinguishable recording be made? This, I believe, is the lure of the hobby. The holy grail. The white wail. How close can I get?