Ween cropped up on the list some months back so sorry to back track, but I'm really taken with the White pepper album and not sure where to venture next, I welcome any guidance.
White Pepper is definitely the 'poppiest' album, and their previous album The Mollusk is similarly tuneful but a little more convincing and diverse. As you venture further back into their catalogue, it just gets weirder and weirder. You might want to get a listen to their debut God Ween Satan, which is nothing like White Pepper but will give you an indication of how weird they get and how weird you want to go. GWS and The Mollusk are two of my favourites because they show a good cross-section of the early and the late in Ween's career. But if you're coming from White Pepper, you should probably start with The Mollusk, then go back from there, maybe to Chocolate & Cheese...