It depends on what version you're talking about, there have been comics where he can break that barrier...same with Flash. In general (again, depending on version), the Flash is faster than Superman. His entire power base is literally nothing but being able to manipulate the speed force. Look for example at Justice League: War where Flash and Superman are both trying to run away from Darkseid's Omega Beams, Flash pulls it off (though he quips after "whew, never been winded before" so it obviously was stretching how fast he could go). Superman though, while he pulls it off for awhile, ends up losing the race and gets smacked with the beam.
In truth, I dislike it when they try to break the light barrier in comics, super speed is great, but when they flat out violate the fundamental laws of physics I kind of find it a bit annoying. They're all still supposed to be made out of particles with mass, and the law of physics E=MC2 is still the case regardless of who they are. So while it may be conceivable that magic could bend those laws and such, but Supes and Flash aren't magic...if they moved at the speed of light they would wind up ceasing to be particles with mass and would have to become energy. This would be a big problem if it was on earth since we see what happens when matter is converted to energy in nuclear weapons. He would literally turn anything he was in contact with (like the road or anything he bumped) into quark-gluon plasma...the electrons in the atoms that made up his body would undergo nuclear fission and his feet slamming on the ground with that force would cause nuclear fusion with the ground (not to mention the atoms of oxygen and such in the air) he'd be colliding with. So poor metropolis would suddenly have a 180 or so pound nuclear fusion weapon detonate in the middle of the city...given that weight he'd completely annihilate much of the state, kill people a thousand or more miles away and so on.
Actually you should check this out:
https://www.youtube.com/watch?v=V-fL8zopddI
It's a video talking about what all would happen if Superman's fist hit someones face at just 99% the speed of light. And that's just the fist traveling at near light speed, you can imagine the devastation it would cause if it was his whole body...my guess is that he'd wind up ripping space-time and become part of the singularity of a black hole sitting on the planet (which, consequently, would suck for all of us). I'm all for making characters incredibly powerful and all, and if they're using magic like Dr. Fate or whatever then you can kind of explain away how they can do things like that, but when beings that aren't magical start simply flat-out ignoring things like relativity it kind of breaks my suspension of disbelief.
But then we're talking about a guy who can fly and ignores gravity too, so what the hell. :P
--
*+_Charos_+*
"I have often laughed at weaklings
who thought themselves good because
they had no claws."
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