Should I let him wear a wig?

My roommate made this bet with me on craigslist http://chicago.craigslist.org/chc/stp/2132186038.html . He has lost (although you can add time to him if you want, it stays up a few more days, lol) This is what he looks like right now. http://www.flickr.com/photos/57575717@N05/5301315366/ . I think it is funnier with no wig, he says it would be less embarassing with one. Should I let him wear one?