Copyright and the First Amendment exist in tension. The Supreme Court acknowledges this tension but says that copyright law resolves it with two built-in free speech safeguards: (1) by protecting only the expression of ideas and not the ideas themselves (the idea/expression dichotomy); and (2) by allowing the use of expression under certain circumstances (the fair use doctrine). The problem is that these doctrines are notoriously vague, so users often cannot know ex ante whether their uses will be immune from liability. This unpredictably might be tolerable if users could be confident that, if they were subject to liability, any damage award would be limited to a reasonable licensing fee or a share of profits attributable to the infringement. But copyright law allows plaintiffs to opt for statutory damages instead of compensatory or restitutionary damages, and statutory damages can sometimes be punitive and even grossly excessive. This combined uncertainty – of not knowing whether a use will be immunized from liability and what the penalty will be if it is not – means that the idea/expression and fair use doctrines are underutilized. Yet if these doctrines are what resolve copyright’s tension with the First Amendment, they need to be sufficiently viable that users can confidently rely on them. One solution is to make the fair use and idea/expression doctrines more predictable, but this has proven largely illusory. Another is to modify the statutory damage regime to ensure that awards are better calibrated to not chill speech. This latter solution, which has not been methodically explored in the literature, is the focus of this article.