64. The Temptations
The Temptations were Motown's classy act. They also were hit-makers who could evolve.
From their earlier love songs like 'My Girl' they morphed into a different, but still popular sound. With Cloud Nine they more or less created psychedelic soul (and earned a Grammy for the effort). The Temps were so solid that such a radical departure didn't scare them: they could do no wrong.
Key track: Get Ready, 1966, which is incredibly infectious.
63. Buddy Holly
Holly was responsible for the day the music died. The tragedy was compounded by Valens and the Big Bopper, but really, Holly was the incredible loss.
Considering the success and innovation of such a short career Holly would, probably, have gone on to amazing heights. His songs were his own: Holly was one of the first rock singer-songwriters. This was a leap away from the Tin Pan Alley and studio executive model that had been prevalent since, ever. His songs are so well-known it is doubtful they'll ever lose favor.
Key track: That'll Be the Day, 1957, which has become the definitive Holly track.
62. Benny Goodman
Goodman had many aces up his sleeve. One was ferocious drummer Gene Krupa.
The other was a willingness to integrate, and bring a blended swing beat to the masses. When Benny Goodman's band performed at Carnegie Hall in 1938 it showed that swing and jazz had arrived. Nowadays Goodman's clarinet is seldom found in jazz lineups. Yet his legacy of making jazz respectable was nearly incalculable.
Key track: Sing Sing Sing, 1938 ver., which is one of the all-time best pieces of swing.
61. Bruce Springsteen
Springsteen is the perennial everyman. His songs are about long-shot odds on the highways of America.
'Born to Run' may be one of the century's great anthems, and certainly there are many lesser songs like it. Springsteen tried to capture the power of a live performance with studio perfectionism. Pumping all of the excess and extra energy he could muster into the delivery gave a glimpse at achieving impossible odds.
Key track: Dancing in the Dark, 1984, which exemplifies later, synthesizer-friendly Springsteen.
60. Run DMC
Run DMC made hip hop serious. They ushered it out of it's infancy and into new sonic territory.
Previously hip hop had been strictly club and dance-oriented. Very few artists made songs with a message ('The Message' being a notable exception). Run DMC were often funny, but had a little more of an edge than, say, the Sugar Hill Gang. When they paired up with Aerosmith and released 'Walk This Way' they also showed that hip hop and rock weren't so far apart.
Key track: It's Tricky, 1986, which gives them space to have fun.