You'll get an infinite number of snarky comments about the War of Northern Aggression back in the early 1860s but the more modern answer is yes states have take

You'll get an infinite number of snarky comments about the War of Northern Aggression back in the early 1860s but the more modern answer is yes states have taken cases to the Supreme Court with highly mixed results WRT nullification of laws. Its not really the kind of thing where historical batting averages have any influence on next weeks attempt, but historically I think individuals have scored slightly better with the Supreme Court than states have. Its also very fuzzy to categorize when the court case technically involves a private citizen who merely happens to be the states attorney general as his day job, is that a win for the state or just a win for some dude?