Annie Lennox is a classically trained vocalist, an experimental thinker, a down-home soul shouter, and a gender-bending MTV star—all rolled into one. What other pop icon studied harpsichord? She helped make Eurythmics one of the most audacious groups of the '80s, but the solo success charted on our playlist is even more astonishing. Her desire to comfort and connect with listeners is only deepened by her mission to challenge pop fans with strange and unexpected soundscapes.