I know of at least two songs that talk about a girl having a 'pirate smile.' unfortunately, I think the reference is lost on me. I have no idea what a 'pirate smile' looks like.

Was it a pop culture reference of the time that just went out of fashion, like 'bette davis eyes?'

When I googled it, all I found were lyrics for songs, blogs, smileys wearing eye patches, and other equally useless items.

Just found your thread...

I googled too, and came up with many like those:

Google Image Result for http://image38.webshots.com/38/3/33/91/2661333910086364712WwyEEG_fs.jpg (http://images.google.com/imgres?imgurl=http://image38.webshots.com/38/3/33/91/2661333910086364712WwyEEG_fs.jpg&imgrefurl=http://travel.webshots.com/photo/2661333910086364712WwyEEG&usg=__n2xVsjDF9O4757gYwcHjnwbxA1I=&h=1728&w=2304&sz=269&hl=en&start=45&sig2=4GaSwhJdwLEWHORLmMtPKw&um=1&tbnid=NNkPiXhdkDvSJM:&tbnh=113&tbnw=150&prev=/images%3Fq%3D%2522pirate%2Bsmile%2522%26ndsp%3D20% 26hl%3Den%26rls%3Dgm%26sourceid%3Dgmail%26sa%3DN%2 6start%3D40%26um%3D1&ei=9TBGS9-3NpiekQWjtIH2Ag)

Google Image Result for http://softeuropean.files.wordpress.com/2009/10/metro2.jpg (http://images.google.com/imgres?imgurl=http://softeuropean.files.wordpress.com/2009/10/metro2.jpg&imgrefurl=http://softeuropean.wordpress.com/2009/10/&usg=__QtSrKR_2Cw3-EUk7_4CAyzrUsR0=&h=306&w=407&sz=56&hl=en&start=51&sig2=AEkWahmuoG9wdcOb41CpgQ&um=1&tbnid=ciLPfdK-dWMbgM:&tbnh=94&tbnw=125&prev=/images%3Fq%3D%2522pirate%2Bsmile%2522%26ndsp%3D20% 26hl%3Den%26rls%3Dgm%26sourceid%3Dgmail%26sa%3DN%2 6start%3D40%26um%3D1&ei=9TBGS9-3NpiekQWjtIH2Ag)

So it's someone who's missing a front tooth?

Not sure HH, I think it is more the wide eyed look with a suspicious smile. Kind of like in the movie Treasure Island when the pirate was being devious...

so it's someone who's missing a front tooth?

Well, that was my guess... :)

Maybe like a gold digger kind of smile? (you know, pirates looking for booty?) Or maybe like a girl with gold teeth?. ( - not tacky at all ;))

Those don't really seem to make sense within the context of the songs, but they're as good a guess as any *shrugs*

I think it is more like a smile where one side of the mouth is lower than the other.Like when a Pirate says arr...