One June 1, 1999, R&B and soul singer David Ruffin, best known for his work with the Temptations, passed away from an apparent drug overdose. He was 50.

Signed to the legendary Motown Records, the Temptations reached the peak of popularity in the 1960s and '70s and are credited as leading influences of the R&B and soul genres. Trained in gospel music, Ruffin was one of the lead singers of the group from 1964 to 1968, enchanting fans with his raspy baritone on hits including "My Girl" and "Ain't Too Proud to Beg."

Over the years, however, he struggled with cocaine addiction and entered rehab for the first time in 1967.  

Despite great success with the group, he parted ways in 1969, venturing out onto a moderately successful solo career. In 1986, he was inducted into the Rock and Roll Hall of Fame for his work with the Temptations.

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(Photo: Detroit Free Press/MCT /Landov)