We need to put some deep thought into this, because a sinking boat is a serious matter. Assuming we are talking about all characters mentioned in The Lord of the Rings, the obvious first one out of the boat is Drogo Baggins, followed closely by his wife, Primula. Those two are natural boat rockers (and heavy ones, at that). Next comes the ultimate boat rocker, Gandalf! With his penchant for causing trouble, he has got to go. After him goes Frodo, Bilbo, and Elrond, so that there is sure to be room on the ultimate trip to Aman. And just to make sure there is passage if I end up having to delay my journey, the other three Straight Path Boys go in the drink as well: Sam
*splash* Legolas
*splash* Gimli
*splashhhhhhh*. Finally, Bergil gets pushed into the water, since he was a punk. Plus, Pippin slipped me 12 silver pennies.
Boromir, on the other hand, is a keeper, since he was able to keep a boat floating even after a tip over Rauros! And we can't toss Cirdan, since he's the one who knows the way to the Undying land. Also, Galadriel, Eowyn, and Arwen are welcome on my boat anytime