Why can't I set my iPod to shuffle songs within a playlist?

My iPod 160 GB Classic runs version 2.0.4. My iPod Nano (version 1.0.2) has that feature. In settings I've set shuffle to "songs".

You can set an iPod Classic to shuffle in a Playlist. Well, my Classic (running 1.1.2 PC) can.
What are you doing after setting shuffle to songs in the Settings menu?
What you need to do is scroll down to the Playlist of your choice and either:
highlight the Playlist and press the Play button (which will play a song at random from that Playlist). When that song finishes, another song will be played - at random - from that same Playlist
enter the Playlist and choose a song that you want to be played first. When that song finishes, another song from that Playlist will be chosen - at random - to be played.
When songs are being played in shuffle mode (the random choice of song), you will see the shuffle icon in the top right corner of the screen. (It's the same icon when in shuffle albums mode.) What happens, that is different, in your case?

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