Screenshots!
The first window is command.com, the command line in Win 9x and ME.
The second window is cmd.exe, the command line in Windows 2000 and above.
Look at the folder naming convention. That's one difference.
Take a look at the years. 2001 was the last year when MS support MS-DOS, when the first NT family was released (if I'm not wrong).
Open Task Manager now. You will find a program called ntvdm.exe. That's MS Virtual Machine, and is used to run 16-bit programs, without interfering with the other 32-bit applications. Otherwise, you will get an error trying to run a 16-bit program.