Should I let him wear a wig?

My roommate is losing this bet http://chicago.craigslist.org/chc/stp/2132186038.html (you can still add time btw, lol). He says it would be less embarrassing if I let him wear a wig, I think it is funnier without. Here is what he looks like without (took it this morning): http://www.flickr.com/photos/57575717@N05/5301315366/ . Should I let him or not?