Some content, especially online, is freely available, such as many pictures, Creative Commons content, and video game modifications. If the creator never makes any money from selling said content, is it still possible for him to collect statutory damages upon copyright infringement? It would seem that actual damages would be $0, and so not possible to collect.
First, a clarification: statutory damages are damages that are prescribed by the statute rather than being based on actual loss.
In both Canada and the U.S. even if the copyright owner was not attempting to profit from the work (thus realizing no actual damages), they could recover any of the infringer's profits that are attributable to the infringement. (17 U.S.C. §504, Copyright Act s. 35)
In both Canada and the U.S., the copyright owner can elect to recover statutory damages (described below) instead of actual damages and profits. Even if there are actual damages and profits that the plaintiff could recover, the extra effort and cost associated with proving those may cause a plaintiff decide to recover statutory damages instead.
In the U.S., statutory damages can be sought if the infringed work was registered at the time of the infringement (roughly). (17 U.S.C. §412)
Statutory damages range from $750 to $30000 per work. (17 U.S.C. §504)
In Canada, registration is not required in order to be eligible for statutory damages.
Statutory damages in Canada range from $500 to $20000 for all infringements in the proceedings if the infringement is commercial infringement, and from $500 to $5000 for all infringements in the proceedings otherwise. (Copyright Act s. 38.1)
Of course it is possible to collect significant damages.
If I create a work and make it available without payment under some license, then you must assume that I have my reasons to make it available for free to those who adhere to the license and not to others. And that I might be willing to allow you the use without adhering to the license for a very generous payment.
If you want my work without adhering to the license, you can't just use it. You can contact me and ask whether I would be willing to sell you the work under a license that you like better. If I'm willing, you need to pay. If I'm not willing, you can't use it.
So it's quite obvious, and has been recognised by courts, that if you commit copyright infringement, then I can sue you, and the damages are either statutory damages, or whatever the market value of this software under a license that you find acceptable would be.