problems putting music on usb drive

I have a 2gb kingston usb drive. The problem is once I get to 114 items or 501 mb, I get a error message saying cannot copy “song name”: the directory or file cannot be created. WTF is wrong. I have enough room on the drive. It just stops at a certain period. What am I doing wrong???

I tried to format it also. Any ideas?

if I take all the music from limewire and put it into a file on my desktop then transfer that file to the USB drive, it loads find. I am just hoping my kenwood flipout can open the USB drive then open the file inside.

is it a fat32 format?

http://static.howstuffworks.com/gif/hammer-1.jpg

im going to the garage

just FAT, is that the problem?

ewww that might be. you have some file namerestrictions and such. try to format it to NTFS and it should solve your problem