Specialized "The Cup" seats
 

I'm interested in what people think about them. It came stock on my Roll Low Entry and I switched it for an old Brooks seat that I had but the Brooks isn't very comfortable and, since I'm riding more upright, I'm thinking I should give it more of a chance and switch back. Or something else for this type bike?

I wasn't familiar with that model. I looked it up. It is designed to provide greater comfort on upright bikes. Comfort is both subjective and variable from one anatomy to another. Nowhere does that play out more than it does with seats. Seat demo programs are great and some shops have a fee loaner program for take-offs, so you might have some luck there. Unfortunately seat comfort is a trial and error process.

Look at the Cloud 9 seat. Have one on my cruiser and my wife also has one on her cruiser. The Cloud 9 seat works very well and I can easily do 20 miles on it without discomfort. Anything over that and I am on my road bike.
The Cup seat looks suspiciously like a standard pan saddle with shaped foam then marketed as something special for 80 bucks.

Which Cloud 9 do you have?

since you have the saddle in question, why not try it out?
No one here can tell if it fits you.

I never used that saddle, but assume there are X people in the world who like it, and Z people who don't like it.

I'd like to hear from both and their reasons why. Type of riding they do and body characteristics.

This is really the ultimate answer when it comes to seats. In the end, discussing it online is only good for giving you some ideas about other saddles to try; the key part of the process is still you actually getting your butt on the different options for an extended length of time. Even someone with a similar body, bike, and riding style to you will find comfort and agony on completely different saddles to what you will experience. At the end of the day you just need to put in enough miles (while making adjustments to the position of the saddle) to find out if a saddle works for you.

I rented a Roll that had a "the cup" seat. I hated it. The way the seat is designed the outer edges of the seat for a cup to hold your behind in place. All it did was cut into my rear the entire time. I usually use a wider seat, 155mm.

I also have a Giant Connect upright seat that I like. Came on my Escape hybrid new.

What's your body type" Height? Weight? If you don't mind my asking. I'm 6'1, 165#.

6 ft, 225 lbs.

Thanks, that's helpful. I just bought a used Giant Connect Upright on ebay. We'll see how that feels.