Right click on any clip and choose View Options. Place the check mark next to Display Clip Contents.

There are some rare occasions where the contents of your Picture Cache directory have become corrupted and will keep Cakewalk from displaying clip contents. To
correct this problem, delete all of the *.WOV files in your Picture Cache directory.

Last, try this: Locate the file AUD.INI in the Cakewalk directory, double click it, and take a look at the line PictureDir=. If the path after the = is not pointing to the
current installation of Cakewalk, edit it now, then choose File | Save and restart Cakewalk. (Back to top)

How can I have Cakewalk redraw the waveform display during playback?
You can enable a setting called DrawPlayingAudio. You need to add the line below to the [Wincake] section of your CAKEWALK.INI file:

[Wincake]
DrawPlayingAudio=1