A few interesting tidbits:
In Top Rank, Inc. v. Allerton Lounge, Inc., 1998 WL 35152791 (S.D.N.Y. 1998) then-District Judge Sotomayor rejected the magistrate judge's report and recommendations on statutory damages as insufficent, stressing the need for deterrence:
The Court agrees with the Magistrate Judge that the facts of this case do not warrant a high end statutory damage award. A wilful infringement, which the Magistrate Judge found, combined with a wilful default, however, warrant an award greater and more significant than one which corresponds so closely to an estimated loss to the plaintiff. The Court agrees with the defendants that statutory damages must be sufficient enough to deter future infringements and should not be calibrated to favor a defendant by merely awarding minimum estimated losses to a plaintiff.In Peer Int'l. Corp. v. Luna Records, Inc., 887 F.Supp. 560 (S.D.N.Y. 1996), Judge Sotomayor imposed liability on the owner of the defendant corporation -- personally:
 Individuals who have the right and ability to supervise infringing copyright activities and a direct financial interest in such activities are not shielded from liability even though they have no actual knowledge of the infringement. The Second Circuit has held that the imposition of vicarious liability, even in the absence of actual knowledge, on those who fail to supervise the conduct of primary infringers better effectuates the policies of federal copyright law. Gershwin, 443 F.2d at 1162; Shapiro, 316 F.2d at 307.And again she recognized that statutory damages are about deterrence -- not only compensation for actual loss:
 The statements Abel De Luna made while being deposed indicate that he is vicariously liable, jointly and severally with Luna, for any copyright infringement committed by Luna. He is president of Luna, and he concedes that he “determine[s] what is done and what isn't done in the corporation.” De Luna Dep. at 12, 21, 150. He is also Luna's sole shareholder and director. De Luna Dep. at 12-13, 21. Moreover, Abel De Luna admits that he did nothing to stop the distribution of the compositions at issue after he was served with the Complaint in this action. De Luna Dep. at 66-68, 154-55. I therefore find that Abel De Luna is individually liable for Luna's copyright infringement because he had the right and ability to supervise Luna's activities and a financial interest in the exploitation of the copyrighted materials.
Congress's provision allowing for a greater award where willful infringements are found, however, indicates that statutory damages serve the dual purposes of the Copyright Act-compensation and deterrence.I look forward to reading the rest of Judge Sotomayor's copyright opinions. So far, I like what I see.
Because of defendant Abel De Luna's willful infringement of plaintiffs' copyrights and his continued infringement after the initiation of this action, I find that substantial statutory damages are warranted to deter him from future misconduct.