15. Ween
They may have recently called it a day, but Ween was, for some time, probably the most popular weird rock band in the world. The main project of Dean and Gene Ween (Mickey Melchiondo and Aaron Freeman), Ween was a wholly unrestricted group that skipped genres with wilful abandon and a sharp, hilarious sense of humour. The spectrum of sounds across their albums is ridiculous. There's Beatles-esque pop on Even If You Don't, references to Steely Dan on Pandy Fackler, Bayou blues on Voodoo Lady, show tunes on I'm Dancing In The Show Tonight, prog on Buckingham Green, house on Friends, and more styles on their incredible album Quebec than you could ever possibly imagine. While this could come across as silly or a gimmick, the band's wicked humour (check out songs like Hey There Fancypants, Slow Down Boy, Help Me Scrape The Mucus Off My Brain and pretty much everything on their hazy oddball masterpiece The Pod) makes their work stand out as just genuinely enjoyable. Ween are a must-listen band. They may not always be as "difficult" as some of the others on this list, but their weirdness is never in question. https://www.youtube.com/watch?v=6PAzqBUNlCs