Make sure your USB drive with a bootable OS is attached. Start the VM, youll boot into Plop. First, right click the USB icon on the bottom right corner of VMware Player, and click Connect Disconnect from Host. Wait a couple of seconds, then click inside the Window, and select the USB option using the arrow keys on your keyboard. And now youll be booting into your OS from the USB. Not only you can boot into Ubuntu from a bootable USB, but you can boot into any bootable OS using this method DSL, Puppy, or even Windows Installation ISO, whatever bootable OS you have on the USB. Not quite handy perhaps, but still geeky Boot From a USB Drive Even if your BIOS Wont Let You. Download Plop Boot manager.