I never heard the Uptowns, but I owned both the Amperiors and CAL and think that they're both different. The CAL is one of my all time favorite headphones and I really enjoy its signature. However, they are much bassier and not as "fast" as the Amperiors. The CAL have a slightly darker signature which makes it great for EDM/hiphop/rnb, with kind of rolled off but nonfatiguing highs (The Amperiors's highs were a bit too much for me at times, and although they were exciting, fatigued me after about 30 minutes of listening). Isolation on the CAL will not be as good as on the Amperiors, but they are FAR more comfortable (one of the most comfortable pairs of headphones I ever used). The signature is too different from the Amperiors for me to gauge how much of a drop in sound quality, but if you've listened to M50s or Vmoda M80/M100s, then you can have a better idea of what the CAL sounds like.