I have been around since version 2 I think.  Purple and black.  
 
Some of the fond and not so fond memories
 
The Panic Button on older Cakewalk stuff 
(an icon that looked like the facial expression of this sort of)

 
Sound Globs
http://www.oldschooldaw.com/forums/index.php?topic=3182.0
 
Syncing ADATs to Cakewalk's Fabulous (seriously) midi composition DAW.  
 
A horrible misstep on Sonar 1 after strong development at the end of the Cakewalk Pro Audio line.
 
The attempt at a second industry standard to VSTs thru DXi stuff (there were some great little plug ins for the time)
 
Man - with nearly 30 years association with 12 Tone and its successors, I feel like I have lost a family member.