No one saw Sgt. Pepper’s or Sandinista! coming. Neither sounded like anything anyone had done before, and they’re emblematic of why The Beatles and The Clash are two of the most important rock bands of all time. They took crazy risks, even though it meant alienating a lot of the teenyboppers and punk purists who’d made them famous and afforded them the luxury of experimenting. That anything-goes spirit is often lacking among today’s artists, perhaps because the Internet has created a culture of niche audiences with very specific tastes, but it hasn’t completely disappeared. Through their music and/or offstage antics, the following 10 artists keep us guessing, risking our goodwill in the name of creativity. It’s a gamble the greats always take.

March 12, 2014 | 1:39pm ET
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