Viviano grew up on Detroit's east side, and attended the University of Michigan at Ann Arbor, graduating summa cum laude with a Bachelor of Fine Arts degree.

He soon came to the realization that, in order to compete in the field, he needed to choose a specialty, stating that what one sacrifices in width and breadth one gains in depth.

However, in 1980, he was contacted by Mad Editor Al Feldstein, who told him that their usual cover artist (Norman Mingo) had died, and asked Viviano if he would provide one for the magazine.

Advertising Lou Silverstone and Mort Drucker's take-off Dullus, the cover of #223 depicted actor Larry Hagman in his role of J. R. Ewing from the television series Dallas being shot through the ear with an Alfred E. Neuman-emblazoned flag.

In 1994, Mad editors Nick Meglin and John Ficarra invited Viviano to come on staff at the magazine, but he declined in order to focus on his freelance career.

In late 1999, they again extended the invitation, this time for the position of the magazine's Art director, and Viviano, now the father of a four-year-old girl, accepted.